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Table of Contents
Read Me First ............................................................... 5

What’s New in Version 1.1 .................................................. 6

Introduction ................................................................ 7

Quick Start .................................................................. 9

Be Your Own Strategist ............................................. 11

Know the Principles of Successful Planning ............... 14

Make Better Promises to Yourself ....................................... 14

Reduce Mistakes by Deciding in Advance ............................ 15

Define 100% as Peak Sustainable ...................................... 18

Define “Productive” for Yourself ......................................... 20

Map Your Natural Style .............................................. 21

Elements of (Natural) Style ............................................... 22

Approaches to Planning .................................................... 27

Review Core Concepts ............................................... 35

The Tools You Use ............................................................ 36

The Components of Productivity Tools ................................ 42

The Process of Using Your Tools ......................................... 58

Choose Your Tools ..................................................... 61

Audit Your Existing Technology .......................................... 61

Select Your Task App ........................................................ 64

Get Started with Your Task App ................................. 81

Document Your Old System .............................................. 82

Get Used to Your Tools ..................................................... 82

Pick a Review Period ........................................................ 84

Set a Planning Window, if You Like ..................................... 85

Create Your Mandatory First Project ................................... 85

Run Both Systems Side by Side (Temporarily) ..................... 86

Work with Your System ............................................. 91

Store Ideas in Collection Points ......................................... 91

Do Things ....................................................................... 93

Manage as You Go ........................................................... 94

Process Your Collection Points ........................................... 97

Implement Best Practices .......................................... 99

Planning Techniques ........................................................ 99

Time Estimation Techniques ............................................ 105

Satisfaction Techniques .................................................. 111

Manage Your “Yak Shaving” ............................................. 113

Track, Review, Adjust .............................................. 121

Projects ........................................................................ 121

Individual Tasks ............................................................. 123

Collection Points ............................................................ 125

Manage People (Gently) .......................................... 127

Make Liberal Use of Waiting Fors ...................................... 127

Set Expectations ............................................................ 129

Manage Sideways and Upward ......................................... 131

Fail Successfully ...................................................... 136

Recognize Your Major Triggers ......................................... 137

Identify Your Situation .................................................... 139

Keep Your Priorities Straight ............................................ 141

Start Over .................................................................... 142

Declare “Project Bankruptcy” ........................................... 143

Keep More Notes ........................................................... 147

Review and Generalize ................................................... 148

Transition to Normal ....................................................... 148

Reward Yourself ............................................................. 149

Understand Your Brain, Understand Your Body ....... 150

Experiment on Yourself ................................................... 150

Try These Changes ......................................................... 152

Consider Everything ................................................ 157

The First Month ............................................................. 157

After Three Months ........................................................ 159

Six Months or So ........................................................... 159

A Year or Two ................................................................ 160

Are You Rereading This Book? ................................. 162

New, and You Read the Entire Book .................................. 162

You’re Confused About Something .................................... 162

It’s Been a Year, My Reminder Sent Me ............................. 165

About This Book ....................................................... 166

Ebook Extras ................................................................. 166

About the Author ........................................................... 167

About the Publisher ........................................................ 168

Copyright and Fine Print .......................................... 169

Read Me First
Welcome to Take Control of Your Productivity, version 1.1, published
in March 2020 by alt concepts inc. This book was written by Jeff
Porten and edited by Joe Kissell. See About This Book.

This book provides you with the tools and information you need to
create or improve your system for managing your goals and projects,
both professional and personal, with concrete steps and strategies for
implementing your tools and workflows, improving your results, and
avoiding common pitfalls.

If you want to share this ebook with a friend, we ask that you do so
as you would with a physical book: “lend” it for a quick look, but ask
your friend to buy a copy for careful reading or reference. Discounted
classroom and Mac user group copies are available.

Copyright © 2020, Jeff Porten. All rights reserved.

Updates and More

You can access extras related to this ebook on the web (use the link
in Ebook Extras, near the end; it’s available only to purchasers). On
the ebook’s Take Control Extras page, you can:

• Download any available new version of the ebook for free, or buy
any subsequent edition at a discount.

• Download various formats, including PDF, EPUB, and Mobipocket.

(Learn about reading on mobile devices on our Device Advice page.)
• Read the ebook’s blog. You may find new tips or information, as
well as a link to an author interview.

If you bought this ebook from the Take Control website, it has been
added to your account, where you can download it in other formats

and access any future updates. However, if you bought this ebook
elsewhere, you can add it to your account manually; see Ebook Extras.

What’s New in Version 1.1

Version 1.1 of this book updates the text to reflect changes in both
software and approaches by the author. The most significant changes

• Updates to software listings to reflect new features since the 1.0

release; see Choose Your Tools

• Additional tips and methods developed by the author while practic-

ing what he preaches, for example in Review Core Concepts and Get
Started with Your Task App

• Rewrites to some text when feedback indicated the initial language

was confusing

Most educational systems are designed with two objectives. The
obvious one, which even young children grasp, is to teach students
things they should know. The sneakier one: students are also learning
how to learn, and methods they’ll need for future self-education.

Oddly, little attention is paid to how to work. The usual advice is solely
“apply yourself” and “work harder”—and that’s parallel with increasing
responsibilities and more dire consequences from falling short.

Eventually, “work harder” stops working. If that’s the only tool in your
toolbox, no wonder you’re having difficulty. Your body and mind have
limits, but demands on you do not. You need better methods.

Everyone has a first time picking up a book like this one, and it’s
almost always a response to frustration about their DIY methods. It
doesn’t matter what you do—student, career professional, self-em-
ployed, retired—if you do things, you can become dissatisfied with how
you organize yourself or your results. There are three rough categories
that describe that feeling of dissatisfaction:

• You’re exasperated with what you’re doing, or with the outcome of

what you’re doing. Either it’s quantitatively lower output than you’d
like or it’s qualitatively divergent from your larger goals (which you
may have never articulated).

• You can feel external pressures and the metaphorical heat increas-
ing, and you have to proactively increase your skills to match.

• You’re already in crisis, and you know you should do something

differently, but you don’t yet know what.

In this book, you’ll learn strategies for all three. The process of improv-
ing your productivity and skills is ongoing, but crisis management is
somewhat different, with an approach you can use as needed.

I’m an expert because this is the book I desperately needed to read a

long while back. I’ve read nearly all the other popular ones over the
years. Most had good ideas (and those that didn’t were highly enter-
taining, in ways the author clearly didn’t intend). They fell into two
groups: interesting theories that fell short of telling me what to do at
2 P.M. every Tuesday, or books with specifics that worked well so long
as I was the same kind of person as the author.

I’m not going to do that to you. I’m highly idiosyncratic, and so are
you. You’re not going to do exactly what I do when you finish this
book, which contains very few “point here, click there” instructions.
Instead, you’ll learn detailed steps for building something similar to
the examples I discuss, but with plenty of latitude to fit your own
needs. You and I are going to end up with similar houses, but yours
will be a different color, with your own furnishings, and maybe a

I spent 20 years discovering how to build my house, and learning the

reasons behind what works and what doesn’t, before I invented a
system that worked well and worked reliably. Your process will be
measured in weeks or months, because you’ll skip most of the trial and
error, and learn from my mistakes. (In some cases I’ll tell you what
they were, but most of the time I’m omitting horrible and time-con-
suming advice.)

I’m different in another way: I’m diagnosed with bipolar II and atten-
tion deficit disorders. My productivity system acts as an outboard
brain, to help me through the times when my own brain is dysfunc-
tional. When I’m depressed or hypomanic, my work capacity radically
changes. Meanwhile, my ADD means I am literally unable to pay
attention the way most people can.

What this means for you is that it doesn’t matter who you are, or what
you’re dealing with. You’re not the exception who can’t use these
techniques. The more uncomfortable they feel, the more they’ll help. If
they can work for me, they can work for anyone. You just have to
determine how they should fit to you, instead of the other way around.

Quick Start
This book is designed to be read repeatedly, as you come back to
whatever needs a refresher, but I recommend you read it linearly the
first time. Skipping parts may confuse you, or cause you to miss
important steps. When you read it again—the book recommends when
you should!—do so in any order you wish.

Everything you need is in these pages, but there is also additional

information that was either useful but secondary to the main points or
only applicable to some readers. I’ve moved that information to the
web. At times you’ll see this, to let you know what’s there:

Web content: These asides point you to specific related posts on the
book’s blog. There is also an index post that includes every link to the
blog in this book, and informs you of anything that might be added or
updated after publication.

Here’s what you’ll find in this book:

Learn Key Concepts

• Be Your Own Strategist and Know the Principles of Successful Plan-
ning to learn what a productivity system does for you, and how best
to use it. When you Map Your Natural Style, you’ll be examining
yourself so that what you build is perfectly tailored to your own
unique requirements.

• Don’t skip Review Core Concepts, or you’ll find later chapters to be

rather confusing. The book redefines some common words for
specificity and creates a few new terms.

Get Up and Running

• You need to Choose Your Tools based on your own requirements
and preferences. You may need some new apps, and maybe a few
new gizmos and nontechnical tools as well. You may also change
how you use your existing tools.

• Then it’s time to Get Started with Your Task App: set up your tools
and add your first projects (including one I provide that helps you
manage your new system).

Work with and Revise Your System

• When you Work with Your System, you’ll follow a step-by-step
process to make your tools work for you, and you’ll actually do the
stuff you’re managing.

• There’s never a bad time to Implement Best Practices, but this is the
point where the steps will make the most sense to you, now that you
have some experience working with your system.

• Track, Review, Adjust is not only crucial to making your system

work for you, it’s equally valuable for everything that lives in your
system. Here’s where you make sure your planning and reality are
in sync.

Make Your System Work Better for Yourself and Others

• There are people you rely on, and those who rely on you, and you’ll
incorporate all of them in your planning as you Manage People

• It’s natural to have times when things get out of whack; when that
happens, Fail Successfully.

• You have to Understand Your Brain, Understand Your Body to be

aware of and improve your most important tools.

Take the Broader View

• Consider Everything. Reviewing your system periodically to make
sure it’s meeting your larger goals isn’t only a good idea, it’s a
required step.

• I recommend that you come back to this book for annual or biannu-
al checkups when things are just peachy, but you might need to
return to it sooner if you run into difficulties. I provide instructions
for each of these occasions where I ask Are You Rereading This

Be Your Own Strategist
You have many things to do and think about. Good planning makes
that easier. I’ll be using the word system to describe the places where
you do that planning—the apps you use, the other tools you employ,
the physical and virtual locations where you store things for later;
literally anyplace where you store useful information or physical items.

Note: I use the word “place” loosely, so I’ll clarify that a place is

sometimes a physical location, and sometimes a virtual space. Your

office is a place, and so is the desktop on your computer. It will be

clear from context which I mean.

Here’s how that all works together:

1. You load your system up with projects, tasks, goals, and information
that you want to manage.

2. You work with your apps and other tools to set rules for how every-
thing should be processed—for example, when a task needs to
repeat, or when one task has to precede another. You choose your
priorities and what’s important to you.

3. Based on the rules you’ve set, your system spits out lists of projects
and tasks, telling you where to go, what to do, and when to do it.

Usually, this starts with a master list that may change daily—it’s the
first thing you reference—while other lists guide you at specific
times or places, or when you’re in a certain mood. The lists show
only what you need, when you need it, and get the distracting rest-
of-everything out of the way.

4. You regularly review your plan, and map out your choices for the
time between now and your next review.

For a preview of how a project looks when it’s entered in your system,
and how it then can be shown in a filtered list, see Figure 1. This
screenshot is from an app called OmniFocus (which you might use, but

aren’t required to), and includes many concepts that I’ll discuss later.
The point of this illustration is to show you: structure and organization
goes in, simple lists of what to do come out.

Figure 1: A structured project view on the left (in OmniFocus for

Mac), and the resulting list filtered by Contexts on the right (on an

A productivity system requires giving up some of your natural autono-

my. If a bright, shiny, and distracting idea happens across your
doorstep, you can’t drop everything to spend two hours on it—or at
least you can’t do so simply because it’s more interesting than what
you’ve already planned to do. If it shows up as a task with a deadline,
or it’s genuinely more important than your current task, that’s a
different story. You’ll learn better habits of discerning what’s impor-
tant from what’s merely new, and the genuinely urgent from the
squeakiest wheels.

Note: What do you do with those distracting ideas? You put them
away for later. You’ll have set times for reviewing all those new
things to see what remains useful, and that’s when you can schedule
them (or save them as a “maybe” for later).

Particular distractions themselves may be unexpected, but the fact that

they will arrive is not, so your planning will include time for them.
Sometimes you’ll have more of them than usual, and only then do you
have to juggle things in the moment. That won’t be your natural way of
working, which makes planned items the usual priority.

Some people chafe at working off of lists generated by software, be-

cause they see it as letting a computer run their lives. The agreements
you make aren’t with your apps, they’re with yourself. When you plan,
you’re making commitments for “future-you.” When you follow
through on those plans, you’re doing what “past-you” set out for you. If
you made the wrong decisions, you can change them if they were
howling errors, but in general you stick to the plan and make correc-
tions during your next review, when you’ll have a week or two more
experience with what you’ve set out to do.

That’s all you need to consider to get into the right mindset. Next I’ll
present key principles to know before you start mapping out your own

Know the Principles of
Successful Planning
Now that you know how to think about planning in broad strokes,
there are a few other things you should know before you get to defining
any specifics. I originally called these “rules,” but that’s not the right
word—no one gets to set rules but you. Then I thought about “guide-
lines,” but they’re too important regarding how much time and trouble
they’ll save you. “Principles” is the word that’s the perfect temperature
for Goldilocks’ porridge.

These are:

• Recognize that your planning is a series of promises you’re making

to yourself about what you’re going to do.

• Map out your projects and tasks to a sufficient level of detail so that
when the time comes, you’re not thinking about how to do it, but
rather are doing it.

• Design your system with a humane understanding of the constraints

on your time and emotional energy, so that your work doesn’t
deplete you.

• If your goal is to be more productive, define for yourself what that


Make Better Promises to Yourself

When you sit down and brainstorm a list of things to do, what are you
actually doing? Writing them down doesn’t get them done, doesn’t put
appointments on your calendar, and doesn’t do any of the several steps
required to go from a good idea (or a required outcome) to an accom-
plished task. What you’re doing when you put something on a list is
making a promise to yourself—usually to do a task, sometimes to
consider it in the future. These lists are personal unless you explicitly
choose to share them; no one but you sees them. Only when you tell
other people what’s there, or when they ask you to add their requests
and you agree, is it a public commitment.

Note: The privacy of your lists is crucial, and should be maintained.

Your plans will contain goals, tasks, and information that are embar-
rassing or even harmful if others know about them. Share only what
needs to be shared, and only with the people who need to know.

To boil it down, your new system will guide you to make three changes:

• Make better promises to yourself about what you can and will do,
and be more reliable about what you promise others.

• Adopt self-improvement approaches that help you form better

habits and respect the existing habits you want to keep.

• Ensure “what you do” fits “who you are” and “where you’re going.”

You choose your own destinations and paths, but these underlying
adjustments make the voyage easier and more satisfying.

Reduce Mistakes by Deciding in Advance

The ad hoc approach to productivity, which everyone without a delib-
erate system uses, requires constantly making decisions in the moment
about what to do next. Maybe you’ve written down some tasks on a
daily list, but once you’re under fire, you’re busily figuring out how to
move things around and what things you might have missed. Likewise,
without planning, you may get to a task only to realize that first you
have to figure out how to do it, or that it can’t be done right now.

Obviously, that’s chaotic, but there are other reasons why it’s a bad

• Constantly choosing may feel like freedom to do anything, but it

leads to wasted and inefficient use of your time. You spend a while

reading email, then a while looking at a document you have to finish
writing, and at the end of an hour you’ve neither cleaned out your
email nor added much to your document. Interesting things might
get done, but not what you’ve agreed with yourself to do. This also
leads to many things started but few things completed.

• When you decide as you go, you open the door to criticizing yourself
later. Say you chose to ignore your email while you finished writing.
Tomorrow you have 100 extra messages waiting and you castigate
yourself for not dealing with them sooner. The time you spent
writing was productive, but it doesn’t seem like the best choice now
that you’re facing your email, so you feel like it was a bad choice.
(This effect and the prior one are called the “paradox of choice.”)

Note: The paradox of choice is best resolved with a decision tech-

nique called “satisficing,” in which you make a good-enough choice

within identified constraints, such as the time and effort required to

make the decision.

• When you’re deciding what to do on the fly, there’s no distinction

between what you’ve planned and what happens to show up. Any
new task can derail you and your priorities. When you’ve planned,
the things in your plan automatically take precedence. New tasks
usually get deferred, until they can be planned as well; exceptions
are only made for literally exceptional tasks.

• According to psychological research, everyone gets a quota of good

decisions per day, although some research disputes this. According
to the hypothesis, different people get different quotas, but every-
one’s quota is finite. A decision uses physical resources available to
your brain, and the only known way to fill the tank is with a good
night’s sleep. Go over your quota and you start making bad deci-
sions. It doesn’t matter whether they’re big or small: each one
counts, whether it’s deciding to quit your job or deciding on a ham
sandwich for lunch. Make too many small decisions and there’s
nothing left for any big ones later.

With a system, you make both large and small decisions in advance,
like “finish the big work project by March” and “take out the trash
every Tuesday,” and then follow the game plan that past-you set out for
you. You weren’t any smarter then than you are now, but you were less
distracted and under the gun, and probably better focused on the big
picture than you are right now.

You’re still in charge, and you can make minor changes as you go—but
in general, you follow the plan. Yes, you should have finished that
document, because your system told you it came first. Later, when you
review your plan (something your system will remind you to do), you
can change things in a way that works better for you.

I can hear some of you scoffing, “Maybe this works for other people,
but my work has far too many interruptions for me to be able to do
this.” It’s true, a monk has it easier in this respect than emergency
dispatchers. To demonstrate how these methods work when you’re
juggling tons of inputs, here are sneak previews of what’s to come
(italicized terms will be explained later):

• You need to make more time available (maybe nearly all of it) for
tasks that arise while you work. In most cases, this means leaving
more open time and not filling up your calendar with events. But it
could also mean creating time blocks when you do particular tasks,
and grouping tasks by type or content into particular times of the
day or week.

• The busier you are, the more places you likely write down things to
get to later, or leave things other people send you, to remind you to
follow up. You’ll use reminders in a central location to make sure
you get back to all of these places, keeping everything under control.

• A fair percentage of your planned work may occur in unplanned

time left open by occasional lulls in the inflow, so you would Use
Sprints, a time management technique to make use of brief periods
of time, more often.

• Your work may be full of scheduled meetings and tasks on deadline

(real or perceived); you’ll put more effort into discerning which of

these are actually Whenever tasks that aren’t due, then Flag Fewer
Whenever Tasks so that they match your available time.

• If you’re in a state of constant distraction and context-switching,

you can Manage Your “Yak Shaving” (continually encountering
prerequisites when you try to do something) by starting a yak list
for every work session.

• The more input you have to juggle from many people, the more
important it is for you to Set Expectations, Document How Busy
You Are, and Enlist Them as Collaborators.

Define 100% as Peak Sustainable

“Giving 110%“ is perhaps the most ridiculous “secret” to productivity

that people espouse. What does that mean? If you could regularly give
110%, guess what? That would be your 100%. You can’t give 110% any
more than you can work 26.4 hours in a day.

Your body isn’t designed to work at its peak capacity for extended
lengths of time. A high-performance physical workout consists of
repeated sets with rest periods in between, for only a small percentage
of your day. Peak creativity, peak focus, and peak energy are the same
as peak physical exertion: you can have it for a while, but not all the

Your goal in reading this book can’t be to transform yourself into a

productivity machine. Impossible demands are, by definition, impossi-
ble. Your goal is to learn how to work at your peak sustainable capaci-
ty. Let’s break this down:

• “Peak” is something you determine for yourself, and it should be

measured against a personal best, not an arbitrary definition of
what you “should do” or even “must do.” We all have our own sense
of what’s a “normal” day and what’s a “good” day. Your peak is
simply your best good day. Don’t plan as if you’re going to have only
good days, but rather plan for normal. You don’t get to rely on a

better track record until you’ve established a better track record—
which is a common result of better planning.

• “Sustainable” means that you’re not running the engine at or over

its maximum for extended periods of time. The number of tasks you
set out to do this week, you can also do over the long term, without
being terrified of maintaining that hectic pace.

• “Peak sustainable” therefore means something less than what your

theoretical peak is on extraordinary days. You can still work longer
or harder to rise to certain occasions, but these will be temporary
and constrained. Your goal isn’t your actual peak, which you
achieve temporarily and rarely; instead, it’s the best you can com-
fortably sustain.

Note: If you hate letting go of “giving 110%,” define 100% as your

peak sustainable and 110% as your extraordinary and rare peak.

Sustainable has to be your usual goal.

The gap between your current normal and your peak sustainable is
your room for improvement. Getting there requires better planning,
better habits, and ongoing refinements to how your system works for
you and with you. It’s not a quick process. But after you’ve improved,
that becomes your new normal—and the same thing applies to improv-
ing this normal that did to your old one (although perhaps with less
dramatic results).

When you reach your peak sustainable as your normal, you might stop.
Pushing yourself further may cut into what makes it sustainable. Or
you may find that you underestimated yourself, and you can aim for a
new sustainable peak; it’s up to you. You can always set higher goals
for yourself, so long as you follow one rule: if those goals turn out to be
unsustainable, dial them back.

What to Do When You Need to Do Too Much
Saying that the best you can do is literally the best you can do should
not be controversial. But it ignores the problem that your demands
might exceed your abilities.
In that case, your first option is to Fail Successfully, using techniques
for dealing with knowing something is coming that’s likely more than
you can handle. But those techniques, along with giving peak unsus-
tainable effort, are good for temporary situations only. For situations
that become permanent, you can’t increase your productivity to
resolve them; they have to be addressed in other ways—some of
which are also described in the Fail Successfully chapter.

Define “Productive” for Yourself

I’m putting on the feathered hat of Carnac the Magnificent, and pre-
dicting that 95% of you aren’t reading this book out of concern that
you’re too darned productive. Instead, it’s probably axiomatic to you
that since productivity is good, more of it is better—and that may be
true, but you need to have a good sense of what “being productive”
means. I’ll discuss this as we go. Don’t automatically say it’s doing
“more things,” as it’s whatever measures you choose for your success:
“the same things with less stress” works too, as does “fewer of these
things and more of those things.”

Map Your Natural Style
You’re coming to this book with established productivity methods—at
the very least, the ad hoc system you’ve developed from your work
habits. In many cases, these came with their own presumptions about
what productivity means: how you implement it, how you measure it,
and how you judge yourself in relation to it. I’m going to refer to all
that as your natural style.

“Natural” in this case isn’t something you were born with, or even a
necessarily positive attribute. What comes naturally to you is a func-
tion of what you find comfortable, which for many people means “the
methods I learned in high school.” The results of what’s natural to you
led you to interest in improving your productivity, so clearly those
methods fall short in some ways. Comfort is an important attribute,
though; you shouldn’t always sacrifice it in favor of improved produc-
tivity, but instead should balance the quality of life that comfort
provides you with the productivity you gain from temporary discom-

Considering your current approach is the first step toward adopting a

new system. You’ll use this information to make better decisions
(starting when you Choose Your Tools).

Document Your Thought Process
In this chapter and a few to follow, your instructions are to think
through some big picture ideas, and come to conclusions about them
for yourself. Almost always, that means you should write down those
thoughts and conclusions. That’s a step many of you will be tempted
to skip—I frequently did at first, when other books told me to—but
there are very good reasons not to skip it:
✦ Some of these decisions require you to be a kind of honest with
yourself that’s intensely difficult, bringing up things you normally
wouldn’t share with anyone but your dog (and maybe not with a
particularly intelligent dog). When you write them down, you’re
sharing them with yourself in a concrete way, more so than if you
keep it in your head.
✦ The choices you make now will drive more decisions in later
chapters. Some implementation choices can accidentally commit
you to the wrong overarching goals. Writing down your decisions
helps to avoid this.
✦ You’ll revisit these big questions in the future, to make sure that
your system is serving any new needs. What you write now is a
snapshot that, in the future, will help you determine specifically
what has changed.

Elements of (Natural) Style

With apologies to Strunk and White for the heading above, here are the
topographical features of the map of your natural style. Note when
they already apply to how you think of your actions and destinations.

Roles, Goals, and Journeys

Nearly everything we do has an unstated why behind doing it; it could
be anything from “this task will make me money” to “completing this
project is part of my purpose in life.” At the same time, some things
you do aren’t projects that you can finish, but instead stem from long-
term and lifetime responsibilities. Clarifying both of these helps you
state your plans in terms that reflect their true importance to you.

A role is something that doesn’t change unless your life changes
radically. If you have kids, you have a role as a parent; that role ex-
presses itself differently at the various ages of your children, but the
basic role doesn’t change, and it never goes away.

You may frequently see your roles as being in the category of “so
blindingly obvious, I don’t think I need to plan it.” That’s fine if you’re
completely satisfied with how you’re fulfilling that role—but by plan-
ning it, you can make explicit choices about how other things move
around to accommodate their corresponding importance.

Alternatively, you may want to plan a role in order to demonstrate for

yourself how well you’re fulfilling it—quantifying the unquantifiable, as
it were. You can’t create a task to “be a better parent,” and you proba-
bly shouldn’t make one to “spend quality time with my kids 30 times
this year,” but you can certainly have one to “make time for my kids,”
then implement that in ways that work for both them and you. (Most
children don’t respond well to “not now, Daddy doesn’t have quality
time scheduled until 4 P.M. Thursday.”)

A goal can be as large and important as a role, but it has a defined
completion. At the smaller end of the scale, goals are functionally
identical to big projects or New Year’s resolutions; at the larger end,
they comprise the “bucket list” of things to do before we die.

Goals should be planned, because if you’ve set a goal for yourself but
it’s not expressed in your planning, you’re leaving its accomplishment
up to chance and memory. Likewise, it’s important for you to be
concrete in stating what you plan as your goals. You can’t decide to be
more financially well-off; all you can do is decide to make more money,
spend less, and save more. But none of those three is suitably concrete,
either. For example, “spending less money” is typically a result of other
decisions you make and actions you take; you can decide to eat out less
frequently to spend less, but the action isn’t spending less, it’s deciding
to cook at home.

Poor Richard’s Goal Setting
In Ben Franklin’s Autobiography, the first part of which was written as
a private letter to his son William, Franklin advises William to create a
grid with days of the week for the columns, and various virtues and
vices in the rows. At the end of each day, he instructs his son to
check off the virtues that were practiced and the vices that were
avoided. Franklin said he used the same system himself, and it gave
him a greater sense of accountability. (It helped that Ben had a
rather libertine view regarding which vices were allowable.)
You can use a modified version of this in your system to reach a goal
or change a habit. If you want to spend less money eating out, you
could set tasks on the days of the week when you’re “allowed” to,
and only eat out when the task appears. Or you could create a daily
morning task to pack a lunch, which presumably will reduce your
need to order a burrito. If your concern is what you eat, set either a
daily task reminding you to eat a sensible lunch or a nighttime task
asking, “Did I eat well today?”
I don’t think Franklin’s advice works for everybody. Some people will
be spurred to better compliance that way. But others will find repeat-
ed reminders of failures demoralizing.

As you adjust to these new habits, you can judge both whether a
particular action you took resulted in progress toward the goal and
whether the emotional cost of that action was worth the goal. If eating
at home reduced the quality of your life by stressing you out from all
the cooking and cleaning, you’re not beholden to that method of
reaching that goal, or even to the goal itself.

Also, you’ll want to determine when to state a goal as a specific one you
can definitively achieve at some point, versus something more open.
“Save more money” is something you’ll never complete; there will
always be more to save. The more specific goal to “save $10,000 this
year” could be a way of feeling accomplishment, but on the other hand
it could be an entirely unrealistic number that only serves to make you
feel bad.

Note: There’s frequently a give-and-take between goal planning and
emotional well-being. Sometimes your plans should give way in favor
of your immediate quality of life, if the actions toward carrying out
those plans are too painful. Occasionally, you can split the difference
by aiming for smaller changes.

I’m using journey to describe anything you do for the enjoyment of
doing it, regardless of what results from it. Most amateur musicians
have no plans of going to Juilliard and no set goals beyond “don’t
embarrass myself if I perform,” but they practice because they enjoy
the process and the feeling of becoming better at it.

In a few cases, journeys take on the mantle of roles, but unlike roles
they usually ebb and flow depending on whatever else is going on. The
purpose in identifying journeys is to make sure they don’t ebb to zero.
If you entirely cut out something that fulfills you, it’s no wonder that
you’ll end up feeling less fulfilled. Plan your journeys in order to make
time for them.

Work, and Everything Else

You may have noted an omission in this discussion of roles, goals,

and journeys: I haven’t related any of it specifically to your career.

This is deliberate.

One theme of this book is that nearly everyone says that other things
are more important than work, but few people act that way. Your
work culture may even require you to say work is more important
than the rest of your life. If you say different things about this at
different times, you have to know which you believe. Either way, it’s
your actions and choices that demonstrate your true feelings.
You may have life goals that include being ambitious in your career—
to be, say, as wealthy as Midas, or to make a large impact doing
whatever your job entails. That’s all fine; the crucial issue is to decide
that, rather than allow it to take precedence automatically. And then
to act accordingly.

Outcomes vs. Benefits
Goals are tricky to define when we phrase them in terms of a desired
outcome but our actual interest is in the benefit they provide. Consider
a goal of being exemplary at your job: if you’re invested in the work you
do, that in and of itself may be your goal. But if being exemplary is an
intermediate step leading to a promotion you want, you’ll instead set
several concrete goals toward that end. (You shouldn’t have a goal of
“get a promotion” because that’s beyond your control, and your goals
should be phrased in terms of what you can do.) That said, if you
achieve those concrete goals but get passed over for the promotion
anyway, you should both give yourself credit for doing what you set out
to do and make decisions about how to change your future actions (or
your job) such that you get the rewards you want.

This can get ridiculously confusing when it comes to money. Nearly

everyone works because they have to (or perceive they do), with most
of us doing things that we wouldn’t do for free in a hypothetical Star
Trek moneyless economy. No matter how much money you have, more
is always better, but studies reliably show there’s a limit to how that
translates to happiness: the correlation of wealth to happiness is a
classic reverse hockey stick, a steep rise followed by a plateau. Money
greatly improves the happiness of people who didn’t previously cover
the basics of Maslow’s Needs Hierarchy, but after that people enjoy
smaller emotional improvements until they reach comfortable middle
class. The relationship between income and well-being drops off a cliff
with further wealth accumulation. It’s fine to want to increase your
income or savings to solve specific problems, but you shouldn’t expect
“more money will make me happier” unless your current income is
well below average (which, please note, doesn’t mean the average of
the people you consider to be your peers).

Note: There is an entire scientific field researching how we’re all

irrational about money. It doesn’t always solve the problems we think
it will, but it can solve problems that we don’t tend to think of as
financial—for instance, someone busy who doesn’t hire a housekeep-
er because they don’t identify as the kind of person who has one.

When planning, be as clear as possible about whether a goal is a
particular outcome or a benefit related to that outcome. In the latter
case, there may be a disconnect beyond your control, so perhaps have a
Plan B should you not get that benefit despite accomplishing your goal.
You may come up with better ways of reaching the same benefit.
Minimum-wage workers may try to increase their income by working
overtime (the availability of which is a goal beyond their control), but
in nearly all cases their better option is to find a higher-paying circum-
stance and undertake a series of goals that makes that outcome more

Approaches to Planning

Your system builds upon several big-picture decisions you make about
how to plan your time and productivity—decisions so large that most
people are unaware they’ve made them. This is particularly the case for
people who rely on the productivity strategies they learned as
teenagers, with only minor modifications since; those strategies were
likely one-size-fits-all, and may have never worked for you. They have
no correlation to who you are when you’re no longer in school, or after
years of work experience.

Trusting Your Brain vs. Writing It Down

Most people, most often, trust their brains to keep everything straight.
It’s the unstated method of people who dash off a daily to do list every
morning; you may refer to the list during the day, but you’re trusting
your brain every morning to consider what’s on deck, and to come up
with a reasonable list of the daily tasks that are highest priority.

Few people should use that method, simply because brains aren’t very
good at it. By definition, what arrives on that daily list is whatever is on
your mind. Important things that don’t catch your attention get
missed—such as journeys and goals without deadlines attached, or
important outcomes that are self-driven with no external oversight.
Planning important things by writing them down in advance is better

because once they’re written down (and you refer back to your list),
they’re unlikely to automatically play second fiddle to lesser tasks.

Note: There are also good neurological reasons to do this. Your

short-term memory has limited capacity, and without training it’s
difficult to reliably move things from there to long-term memory.
When your mental list exceeds your capacity, things get dropped
regardless of importance.

However, writing everything down does come with some costs:

• On the plus side, writing something down means you can allow
yourself to forget it almost immediately. You won’t have to worry if
you’ve addressed everything that hit your radar over the course of
the day; it’s stored somewhere, and your mind is clear.

• On the other hand, relying on notes and lists works only when they
contain everything. If you write down nine things and trust yourself
to remember the tenth, you must also remember that you neglected
to record the tenth thing. That’s two things you’re remembering.

• Writing everything down takes time, and can break your chain of
thought. A good idea, or a new task from someone else, can arrive
when you’re in the zone on something else; you have to be able to
get it down somewhere, and off your mind, so quickly that it doesn’t
distract you.

Note: More neuroscience: Most people, when distracted from the

task at hand, take 20 minutes to fully redirect their attention back to
it. You may think you’re not most people—but most people think
they’re not most people and many are wrong.

• Writing everything down feels silly until you get into the habit. You
think there are things that you “should” naturally remember. If you
actually do remember, and follow through, that’s great. But why not
write it down anyway, to rule out the possibility of forgetting?

Note: Things that you do naturally remember are also worth writing
down when they compete for limited time. If you like doing things in
the first hour of your day, remember that a shower and coffee always
take half of that time; think of it as “a free hour” and you’ll likely
overestimate what you can do then.

I lean in favor of making a blanket recommendation to write every-

thing down. However, there are some people who are excellent at
holding things in their brain. Give the write-it-down strategy a try
regardless. It may lead to some lost time because you’re planning out
things that don’t need to be planned—but in that case you can drop it if
it’s not useful. You won’t know if it’s a helpful strategy until you test it.

Freestyle vs. Structured

Consider the two methods of planning your day shown in Figure 2.

Figure 2: Two different methods of creating lists.

The list on the left is flat—one item listed after the other, without any
hierarchy showing subtasks. On the right is a nested list: either a
heading task has subtasks beneath it or items are grouped together in
some kind of logical way.

The flat method is how most people brainstorm lists. Note that this
method results in a flat list with a mix of simple tasks, small projects,
and vague goals, and most are missing details that are more usefully

included in the nested outline. “Plan the kid’s birthday” is, as shown on
the right, several different tasks that happen in a particular order.
Calling Myrtle is a one-off task, but in the nested list, it groups the
context of why you’re calling her.

Flat lists have a decided speed advantage, but nested lists allow for
deeper planning and bigger projects. Most people have projects com-
plex enough to require nested lists; flat lists are too simple. My recom-
mendation is nested lists usually, flat lists when sufficient.

Note: There are other ways to plan complex tasks besides with an
outline, such as mind mapping. I use outlines as the simplest way to
get where we’re going, but if you prefer a different structure that still
handles complexity, have at it.

Work-Life: Separate or Combined?

It used to be, a few decades ago, that work and the rest of life were
comfortably split. You went to the office, and you worked there; you
went home, and you turned off work mode. Then we invented things
like iPhones and Wi-Fi, Slack and work chats became a 24/7 kind of
deal, and many people are effectively “at work” whenever and wherev-
er their laptop is powered up.

Self-employed people, and everyone who’s now in what we’re calling

the “gig economy,” are even more likely to mix the two. If 2 P.M. is the
best time to see a movie, and 2 A.M. is the best time to complete a
project, no problem. Sometimes the ability to do this an advantage;
other times, work becomes a monster that eats everything else.

For a decade or two, we’ve called this “work-life balance,” and it’s
taken as axiomatic that well-adjusted people get to “have it all.” If one
side suffers due to the other, you must be doing something wrong—
especially if you’re a woman. But that’s obviously poppycock.

Note: I’ve always found the phrase “work-life balance” very telling,
in that “work” gets carved out as the only separate thing from “life.”
Silly me for thinking that “life” includes all the time that I’m breath-
ing, and work is something I do with part of it.

We all know that when work gets rough, we’re going to cancel events in
our “life” to make more time. Conversely, most people agree that a job
that doesn’t accommodate when you or a family member are seriously
ill is a bad job. But we have a blind spot for jobs that routinely take the
place of most non-work activities, so long as they pay well or come
with other perks. They’re seen as “good jobs that require a lot of
you” (not “bad” jobs)—but that’s true only for people who don’t place
much importance on what they’re sacrificing. For everyone else,
they’re bad jobs, just cushioned with money.

There’s another way you have to figure out how to approach the ques-
tion of work-life balance: you must decide whether you’re managing
only your work or the whole kit and caboodle. I personally don’t
understand it, but for some reason people tend to gravitate to organiz-
ing only what they define as their work. When it comes time to think
about what frustrates them, though, their “life” is the source of most of
it. (People are frustrated about money and not having enough of it, but
that’s not work—that’s the benefits of work.) You’ve often heard that
no one on their deathbed says, “I wish I’d spent less time with my
family.” To that I’ll add that few people who didn’t own their own
business, or didn’t view their job as a calling, will say they wish they’d
accomplished more work goals. More frequently, what they most
regret are the benefits they didn’t get, or the outside goals they never
started due to lack of time.

That said, doing your work well is obviously important, for a bunch of
reasons. But it’s of varying importance depending on what else is
going on; until you have some way of measuring those big-picture
priorities, they’re going to be set by default—usually in favor of work,
and usually without compensating you for its privileged status.

For now, decide which of the following approaches better suits your
style and preferences:

• Manage everything: If it takes time, it should be managed.

Otherwise, your preferred leisure activities, and other things you
regularly rob time from, won’t get suitable attention.

• Manage work and big projects: Day-to-day life stuff can go

with the flow; it’s too much effort to try to impose order on it. You
manage only your work and those select few other things that are
big enough to require planning.

• Manage work only: Manage your work and nothing else. The
whole point of your free time is that it’s “free”; trying to manage it
like a project is crazy-making.

I’m inclined to suggest that “Manage Everything” is the proper ap-

proach for self-employed and gig economy workers, for ambitious
people who see 70-hour workweeks as a light schedule, and for people
who thrive in a self-imposed structure (or who know from painful
experience that they require one).

Everyone else should do what comes naturally, with two caveats. First,
anything that you’d regret not doing, or that causes friction between
your structured and unstructured time, should be planned. If Facebook
takes up two hours of your workday, or a Netflix binge causes a night
of only three hours sleep, you should manage it in order to control it—
and likewise if you’re three years behind on the shows you want to
watch, or your friends notice that you haven’t posted on Facebook in a
month and wonder if you’re dead.

Second, if you came to this book because you thought, “my life is out of
control,” you probably have greater need to manage everything than if
you were thinking, “my work is suffering.”

Top-Down vs. Bottom-Up

Deciding whether to plan from the top down or the bottom up involves
implementing some of the observations you made about yourself when
you considered your roles and goals.

Some people work well with big goals and then drilling down, as in “be
fluent in Italian in five years” and then kicking it off with a project to
“complete the beginner audio coursework in the next six months.”
Roles can also fall into this category when they naturally lead to large
goals, such as the parent planning to build a three-story treehouse, or
the community volunteer expanding a Meals on Wheels program to a
new neighborhood.

The alternative is to start small, and group things together only when it
makes sense to do so. You don’t “spend quality time with your
children” over the course of a year, you “read with your kids” three
times a week. You might want to take the kids to Disney World some-
day, which takes time, money, and planning, but it’s not a goal per se;
it happens when it happens. It adds up to “be a good parent,” without
ever necessarily writing that down.

There’s no right answer; there’s only what works for you. But keep in
mind that sometimes the other way will be better. If you’re in the habit
of setting large goals and falling short (because you underestimate how
long they’ll take, or how much time you’ll have), try the same thing
again but bottom-up, which is more likely to start with something you
can chew in one bite. On the other hand, if “take the kids to Disney
World someday” has the unstated clause “before the oldest turns 13,”
more top-down planning is in order to make sure the trip happens in

Commitments, Somedays, and Maybes

Some people prefer to restrict their lists to actual commitments: if it’s
written down, that means they’re going to do it, by jingo. Others have
lists of a thousand things they only might want to do someday. (I’ve
spent 30 years saying I’d like to learn how to play klezmer. If anything,
I’m further away now, because 30 years ago I was better at the
clarinet.) And just about everyone has things they would already be
doing if a genie granted them 208 hours in every week.

Your system can handle all of the above, but you should have high
conceptual walls between them. If you put too much Commitment

chocolate into your Maybe peanut butter, then instead of being an
inspiring list of dreams, your maybe list chides you for how much of it
you’re not doing. In the reverse direction, the optional status of
“maybe” will wreak havoc if it’s let loose on your commitments.

“Someday/Maybe” is a common term for a maybe list, but these are

also two things that should not be mixed. Counting commitments,
there are actually three separate categories:

• Most places in your system are for commitments: projects or tasks

that are not optional when their time comes. Projects may be wait-
ing for a future start date, or on hold indefinitely, but any that are
currently active are a commitment.

• Some places are for maybe projects and tasks: ideas that were good
enough to keep, and perhaps aspirational to consider, but maybe
not to do.

• Someday places are in between. A Someday project is something

you have committed to doing, when you have the time. It’s not on
hold (which implies that it was active for a while, but then stopped);
it’s a never-started. When you finish a few active projects and
consider what else you might want to start, your Someday list is a
menu to choose from.

Someday and maybe places are entirely optional, for when you want to
keep your ideas for future reference. Distinguishing between them and
your actual commitments is not.

At this point, you should have a handle on your top-level life choices
that drive the things you do, as well as various methods picked out for
how you’ll naturally break those things down into projects and day-to-
day tasks. Next we’ll review necessary concepts for good planning—
both new terms and new wrinkles on ones you already know.

Review Core Concepts
Here I present new ways of thinking about concepts you probably
think you understand already. I also discuss new definitions of terms
including tool, project, and due date.

I know, right? What a waste of time! But it’s not—these redefinitions

will save you a great deal of effort. It’s similar to when you learned in
elementary school about gravity: drop an apple, it falls, and the dude
under the tree claims he discovered something new. Then you get to
college and maybe find out that, thanks to Einstein and relativity,
gravity is actually a bend in space, and no one knows precisely how it
works, or why it’s weak enough that you can pick up an apple when the
entire planet is trying to stop you. The simple explanation was a mask
that hid the fact you didn’t understand it.

The core concepts in this chapter are interdependent, but I have to

present them in linear order—books are just like that. To make this
clearer, here is what’s in this chapter:

• The tools you use to organize your projects, collect ideas and notes
for later, and track your progress.

• The components that those tools use and organize. I just used the
word “project,” but what is a project? What’s a task? What’s the
difference between an appointment with your boss and a vague plan
to call your mother on Sunday? Don’t skip this material, because I
introduce some new ways of thinking about things you’ve been
doing for years. See The Components of Productivity Tools, later.

• The process that takes these tools and components, and with you as
the engine, turns capabilities and data into completed projects and
advancement towards your goals.

The entire rest of this book is a continued discussion of that process,

in greater and specific detail. But here, in The Process of Using Your
Tools, I present the broad conceptual strokes that help you under-
stand how those details will fit together later.
The Tools You Use

Ask most people who use a productivity app what their system is, and
they’ll tell you the name of that app. And yes, that app is very impor-
tant—it’s the biggest moving part in your system, aside from you—but
it omits everything else. An app doesn’t make you magically productive
when you launch it, or even once you fully understand its approach.
The app works when it integrates with you, how you think about what
you do, all the places where you put information, and everything you
use to do your tasks.

An app is just a tool, and a tool is anything you use to store, manage,
organize, and do what you do. If you find your kid’s broken toy in the
back seat of the car, and toss it into the cupholder as a reminder to buy
a new one later, the cupholder is now one of your tools (specifically, a
mnemonic device). But it’s not a very good one, because it alerts you to
buy the toy only when you get into your car and see it—when you’re
about to go somewhere that probably doesn’t sell toys. Not a useful
reminder. It becomes useful when another tool prompts you to check
your car for reminders like that toy when you’re not doing something
else—that’s when you can decide to drive to the store, buy it online, or
write it down for later.

A well-organized system includes these types of tools:

• Your task management app: This is the app that other people
mistake for their entire system. It’s first among equals amongst all
the tools you use—not only does it organize most of your work, it’s
also the first place you look when you’re starting your day or picking
up after a break. I’m going to call this your task app for the rest of
this book.

Think of this app as your command-and-control center. You might

do some of your organizing in other places (for reasons I’ll discuss
shortly), but when you do, this app has a special kind of reminder
that tells you when to refer back to it. When you look here, you’re
confident that you’re seeing everything you’re doing or might do,
even if some of the complexity of those tasks lives elsewhere.

You should use a dedicated task management app for your task app,
and you should only have one. There should never be ambiguity
about where to start: you have a single task app, you start in a
particular place in that app, and as you proceed through your work,
it provides a clear path for where else to go.

• Your other productivity tools: Most of your tools will be a bit

more useful than a cupholder. They’re the other apps you use
regularly, the computers and gadgetry those apps run on, and
groups of atoms called “physical objects” where you store and
manage information. I’ll refer to these as your other apps or other
tools depending on which I mean.

You’ll use several tools to plan and organize some things for three
simple reasons: there are things your task app can’t do, there are
things that other tools do better, and there are places and times
your task app isn’t available or isn’t convenient. These tools are
sometimes additional planning apps (such as a drawing app where
you create a diagram to visualize a project), and sometimes are the
same apps you use to complete a task (such as a word processing
document that contains its own outline). And of course, your tools
need not be apps, as some people still prefer a legal pad and a fancy

A few guidelines regarding other tools:

‣ Have as few tools as you need, but no fewer. You want few tools
because anyplace you store or organize information is, by defini-
tion, another place to look. Even when you rely on your task app
to make sure you don’t miss something stored elsewhere, every-
one has a psychological threshold where it feels too scattered.
But you don’t want fewer tools than you need, because when you
need a tool that’s missing, or you use one you have for something
it’s substandard at doing, you end up spending time or feeling
frustration that a better tool could have saved you.

‣ When you have several tools to choose from, the one to use is the
best one for that particular task. You have dozens of apps on
your computer and dozens more on your phone. For that matter,

you can also decide between a computer, a tablet, a phone, and
pen and paper in the first place. Different tasks will have varying
best tools; you want to have enough of a range that none of your
tasks have to be done with a mediocre one.

‣ There are times when a tool is best because it’s the only one you
have available, so have a good one. This applies most often to
tools used while on the go—there are many tasks where it’s better
to use a tablet or a computer, but you can’t use them one-handed
while standing on a crowded subway platform. Or you may be
the type where you enjoy shutting off the internet for a few days,
when you’ll need something that doesn’t rely on connectivity (or
if you’re truly getting away, electricity). If you have a tool avail-
able at all times, a surprising number of tasks can be done during
odd moments in between other things.

• Your calendar: A calendar can be thought of as another organiz-

ing app, but what it does well is so crucial to the rest of your system
that I’m separating it out as a category and a requirement.

• Your collection points: A collection point is anywhere you store

ideas or things that have a followup task, some of which you’ll do
soon, others you’ll later review and organize in your task app. A
grocery list is a collection point, as is saying “Hey, Siri, remind me
to go shopping on Tuesday,” or a dining room table with three
weeks of stacked and unopened mail on it.

Sometimes a collection point stores very simple things; you don’t

need to organize most grocery lists, as you can simply check things
off when you put them in your cart. But if you want to get your
arugula from Whole Foods and your brandied chocolates at Trader
Joe’s, you might use a collection point for reminders that you need
those things, and tell your task app to show the resulting list with
filters depending on where you’re going; this is easier than trying to
maintain separate lists for each grocery store, and trying to have
each list double as a collection point and a checklist.

Good collection points are quick to use, versatile in moving data to

other tools, and collectively ubiquitous—most are only sometimes

available, but they overlap so that you always have one or two at
hand. Every collection point gets reminders in your task app telling
you to go organize them; when you write down something you want
to remember in a new place, you add that place to your task app.

Again, you want as few as you need, but no fewer—collection points

can really grow out of control. But you want enough so you can store
ideas and reminders at any time, because when you don’t have a
place to collect them, you’re storing them between your ears.

Note: You might also have a collection point inside your task app. It’s
frequently called an “inbox,” because a book titled Getting Things
Done popularized both the concept and that name 30 years ago. I’m
using a different term here to avoid confusion with your email inbox.

Components in your system work together because of your frequent

use of pointers, which are the reminders I just mentioned regarding
your collection points and organization outside your task app. Pointers
tell you to look, or do something, somewhere else. For example, a
pointer is the task in your task app that tells you to work on a specific
outline in another document, or the task that reminds you to review
items in the Reminders app, including ones you made using Siri. Every
time you create some kind of external organization, it gets an individ-
ual pointer in your task app, which could point to anything from an
outline document, to your car’s glove compartment (and cupholders),
to the garage wall you’ve covered with Post-It notes and colored string.

A pointers can be as specific as you like, which is a good idea, as it

saves you trouble later. I might use any of these as needed: “Work with
files on your desktop” (a combined collection point and organizational
space for me), “Work with [specific file] on your desktop,” and “Work
with files in [specific folder] on your desktop.”

Like all tasks, pointers can occur once (for single tasks you complete in
one sitting), repeat for a while until a project is finished (I had one
daily while writing this book), or repeat forever for collection points
you never stop using, or for documents you continually add items to
(such as the one I use to keep notes for blog posts). Once you’ve en-

tered a pointer into your task app, it’s just like any other task; you only
need to remember it’s a pointer to develop the muscle memory to
create one every time you need one, and then to delete it after it’s no
longer useful.

Note: “Pointer” is a concept I borrowed from computer terminology.

It’s a bit of programming that tells an app that it should use some-
thing stored at a specific place elsewhere in its memory. This makes
apps faster and more efficient. See why I used it?

Your system is all of the above elements, working in concert. Even if

you’ve never had a deliberate productivity system before, you certainly
have collection points and a few tools you use you organize things. The
difference here is the rigorous approach: every time you put something
into a new collection point, you create a pointer in your task app to
make it reliable to store things there. Every time you use a better tool
than your task app to organize something for which it’s more suited,
you put a pointer in your task app to refer to that tool or document
when you work on it next. If you feel the need to “get more organized”
because things are in too many places, you do that in your task app
(and remove reminders to go elsewhere that you no longer need).

Note: Pointers to use your external organization and collection points

are crucial. Use them frequently, maybe too often; if you’re pointed
twice to the same thing, just skip it the second time. Better twice
than none. You can point yourself to anything: other apps and tools,
places, documents—anything you need on your radar.

The system you come up with can be simple or complex—the direction

you take is entirely up to you, and you should modify it in response to
your experiences using it. When you find yourself frustrated by your
tools, you might add another one on a temporary basis, and keep it if it
works. On the other hand, if you’ve adopted so many tools that you feel
overwhelmed, you’ll drop the ones that are least useful. Crucially, you
may also add tools when your circumstances or needs change, and
your toolset is inadequate for the results you need.

Figure 3 shows an example of a simple system.

Figure 3: A simple system with very few apps used as tools.

Note: The illustrations in this book are mostly taken from Mac
screenshots, only because that’s where I live. When I later discuss
apps you can use, multiple platforms are covered, including Mac, iOS,
Windows, and Android.

In actuality, no one’s system is this simple, because the figure omits an

email app and a web browser, both of which certainly count as tools for
storing reference information that may need further action. But this
could form the core of a system whose owner wants to keep it simple
and straightforward: Reminders and Notes on Mac and iOS to collect
new ideas, a word processor and spreadsheet to complete tasks, and an
app called Things (which I’ll discuss when we talk about specific apps)
as the task app where everything is organized.

I considered including an illustration of a complex system, but it would

have so many arrows it would look as complex as a spirograph. My
own system spans a Mac, iPad, Android phone, and several cloud
services, which requires me to use multiple apps to work with the same
synchronized files; on top of that, I regularly use dozens of other apps
on each device, plus numerous web apps. My task app is extremely

powerful, but it’s not good for documents that need be shared, or
viewed side-by-side with other windows, so I have entire large projects
where the task app simply has a pointer saying, “Go do the project
that’s organized in this particular outline document.” No matter how
many tools I use, or how complex it all gets, my task app keeps it all

The Components of Productivity Tools

Productivity apps have common-denominator components, which vary
in implementation from app to app but share core methods. You have
worked with many of these concepts in the past, but some will be new,
and others will be defined differently because we need new concepts
later to discuss various approaches.

Projects and Tasks

As you’re probably already aware, projects and tasks can be one-time
or repeating: “Write the Waterloo memo” and “Donate the clothes in
the attic,” or “Write the annual report” and “Take out the
trash.” (Sometimes I call repeating tasks “recurring tasks.” They’re
synonymous; I’m just using the word that sounds better at the time.)

Your projects and tasks usually live in your task app, but you may put
them in other tools when they’re better suited for that particular
organization. For example, some files on my desktop are implicit tasks,
meaning that I’ll know exactly what to do next when my attention is
drawn to it.

This is faster than manually adding it to my task app, making my

desktop a better tool for that kind of organization. I have other reasons
to organize in other apps from time to time. All of these places and
documents get pointers in my task app. Sometimes a pointer sends me
to a place where tasks are organized, sometimes to a specific task in
that place—and for things I want to see quickly, both, because either
pointer will get me there and I’ll use whichever one is soonest.

Note: Some calendaring apps can show tasks in your calendar. This
is fine when your calendar gets them from your task app—your tasks
still live where they should, they’re just displayed in two places.
When a calendar app keeps its own list of tasks, be sure pointers get
you there, and consider organizing them in your task app.

Many tasks are not implicit. Just looking at an unfinished spreadsheet

usually won’t tell you where you stopped and what your next task is.
When you describe your next task you save yourself time and effort
otherwise spent remembering it later; the best place to store these
descriptive tasks is your task app. Task apps also allow projects and
tasks to have additional data, such as a start date (sometimes called a
defer date) you won’t or can’t begin before, or notes and URL fields.
It’s possible to replicate these features elsewhere, but at the cost of
doing work that your task app would automatically do for you. Use
other apps only when they’re clearly better; I provide examples when
we talk about specific apps and how to use them.

Subprojects and Subtasks

Projects and tasks seem like straightforward concepts, but there’s a
blurry gray area between them. It depends on how you define a project,
and how granularly you plan your tasks. For example, most of us who
don’t have a butler named Alfred have a recurring need: do laundry.
This instinctively feels like a task, right? “Make stinky clothes clean.”
One step. Simple.

Not so fast. Doing laundry is more complex than it seems on the

surface; it’s just that you’re used to it, so you don’t notice. You can’t do
laundry if you’re out of detergent or, depending on where you live, if
you don’t have change for the machine. So “do laundry” is actually a
project with multiple dependent tasks (Figure 4).

Figure 4: An extremely granular method of doing laundry. Some
people would be less kind in how they describe this level of detail.

Note: The first three tasks on this list are phrased as questions, the
convention I use for “mark this done if the answer is yes, otherwise
it’s something to do.”

Most people see the above as obsessive and fiddly at first; of course
you have to wash your clothes before you dry them. Who needs to be
told that? Sure, combine those steps into “wash clothes” if you like.

But there are reasons why breaking down your projects and tasks into
subprojects and subtasks can be a good idea:

• A granular list makes it very clear when you have a dependency, like
“have detergent.” The more likely you are to do something at the
last minute, the more important it is that you’ve addressed these.
Even when it’s not particularly urgent, it’s frustrating to have to
delay a task you want to do. A checklist, even an “obvious” one,
reduces this problem from rare to nonexistent.
• Many tasks with subtasks like these can be stopped in the middle
and resumed later. The more granular the subtask, the easier it is to
make progress during shorter time windows.

• Granular tasks require some thought during the planning stage. Not
particularly difficult thought, but it’s a moment when your attention
is on how you’ll approach something. That means you won’t have to
ramp up to any given task when it happens.

• Doing several things at once is usually a bad idea, but sometimes it

can’t be helped (and some tasks, like laundry, are so brainless that it
doesn’t matter). With granular lists, you’ll always know where you
left off. This also applies when you are moving the ball forward on
several projects in parallel, and need to switch rapidly from one to
the next.

• Some people enjoy checking stuff off their lists. Makes them feel like
they got more accomplished. This is a bit of a mind game, but
there’s nothing wrong with that if it makes you more satisfied with
your day.

Tip: How granularly should you plan? When the description of a task

is also the instruction for how to do it, that’s as small as you should

get. Whenever a task turns out to be two or three steps once you

think about it, don’t hesitate to break it down further.

The only downside, but it’s a big one: this kind of task management
takes longer to plan. It’s much easier to write down “do the monthly
report” than it is to think through all the steps you need to do it.
Likewise, for anything you’ve done repeatedly, you have most of this in
muscle memory. This is one of those things that feels silly because it
seems obvious. Perhaps. Personally, I have a bad habit of not quite
giving my dryer enough time, and allowing my clothes to finish drying
in vivo while I wear them. Planning for additional dryer cycles helps.

People tend to have one of two polar opposite reactions to this idea:
either this method will work well for you or it will drive you insane. If
you think it sounds batty, only use it after a non-granular task gives
you difficulty. Plan it out granularly before you try it again. On the

other hand, if granularity works for you, there are very few times when
you shouldn’t.

Note: Even for highly skilled people, checklists reduce errors and

oversights. A space mission is crewed by some of the most highly

trained people on Earth; the mission commander uses a checklist

during countdown.

When you’re working with your task app and other apps with similar
concepts, they’ll use varying terminology for these approaches. In
some, any item that has nested tasks is called a project. Others refer to
them as tasks and subtasks. It usually doesn’t matter, but in some apps
you’ll have capabilities with one type that you don’t have with another
(such as how you schedule it to repeat).

Sequential, Parallel, and Available Tasks

The tasks of the “do laundry” project have to be done in order, so doing
laundry is called a sequential project. In a parallel project, tasks can
be done in any order. Shirt and tie are sequential; shirt and socks are

Different levels of planning can have a nested status. Cleaning the

house is a parallel project, because you can vacuum before, after, or
during the laundry. Doing the laundry, however, remains a sequential
project within the larger parallel one.

Note: If you need change and detergent and you have to gather all
the dirty clothes in one place, that’s technically a parallel subproject,
prior to sequential laundry steps. Sometimes it’s worth the trouble to
set it up this way in your task app, other times not (like here).

Sequential and parallel status affect the availability of a task. Before

you’ve put on your shirt, you simply can’t put on your tie. This is an
important distinction, because one of the key features of many task
apps is to hide unavailable tasks from you until you’re able to do them.

Note: The other major reason a task might be unavailable is when
you’re in the wrong place or time to do it. You can’t do your laundry
in your office. I cover this in Contexts below.

There’s another way to order a project or list, which is: not at all. An
unordered list is a collection of tasks that are grouped for convenience,
not because they’re part of the same project. A list of movies you might
watch, in the order you happen to think of them, is an unordered list
(unless you binge them in a marathon). They’re functionally identical
to parallel, flat lists of tasks.

Pointers act just like tasks in terms of how you organize them. Some of
them will be slotted into your projects when you need details stored
elsewhere; for example, why laboriously retype minutes from a meet-
ing with your tasks highlighted in yellow, when you could easily write a
pointer that says “Refer to Minutes-1776-07-04.docx”? Other pointers
simply get tossed into unordered lists in any way that makes sense to
you—you don’t have to find them again, because they have settings
(that I’ll discuss shortly) that bring them to your attention as neces-

Events live in your calendar, which is unfortunately a very confusing
word. “Calendar” is the name of the Mac and iOS app that holds your
“calendar,” which is the colloquial word we use to mean “all your
upcoming events.” Your calendar app lets you create multiple cate-
gories of events, such as “Work” and “Family Shared,” and most apps
call these “calendars.” So you open Calendar to see your calendar,
which might have many calendars.

Head-spinning. When I say calendar by itself, I mean the colloquial

term. When I say something like “appointments calendar,” I usually
mean one of the several calendars in your entire calendar, and I always
mean that when I use plural “calendars.”

All events fall into one of three categories:

• Hard: Anything that must happen at that time, or won’t happen at

all. Sometimes but not always synonymous with “appointments”:
meetings that can’t be changed, your kid’s recital, the time the last
train home leaves the station. Deadlines for your projects and tasks
are not hard events; they’re not events at all.

• Soft: Things that are not a big deal if they don’t happen. You
haven’t called your sister in a while, so you decide to do it Thursday
night. It’s not her birthday or anything; if you skip it, only you will
know you planned on doing it. Also applies to many after-work
networking events, which are vaguely good for your career but
which you might skip if you’re tired.

• Firm: These are in the middle, and they’re a special case. Firm
events are time set aside for things that should happen at that time,
but don’t necessarily have to. There’s a movie you want to see
tonight, but tomorrow evening is free and you can see it then.

The most common productivity reason for a firm event is to set

aside time for a specific task or project—for example, “Work from
1–3 P.M. Wednesday on the report due Friday.” It’s no problem if
that happens from 2–4 P.M., but it’s a big problem if you put it off
until midnight Friday morning. I’ll use the term time blocks for firm
events set aside for specific projects.

Appointments can sometimes also be firm events: for example, a

meeting with a colleague that’s loosely scheduled, and it won’t
matter if it starts 30 minutes late or is pushed to another day if
either of you is busy.

Missing a firm event has different consequences than missing an

appointment. You have the option to skip it like you do with a soft
event, but should you miss it, you usually have to make up the time
elsewhere—which is no big deal in some cases, and extraordinarily
painful in others.

Some firm events can change their “firmness” based on context.
Revisiting the laundry as an example:

• If you reliably do laundry when the hamper is full, and there are
always plenty of clean clothes in the closet, it’s not an event at all.
It’s a recurring task. Get to it whenever, you’ll “automatically” do it
in time.

• If your weekends are booked solid, and you find yourself frantically
sorting clothes at 2 A.M. Monday morning, a soft event to block out a
better time might be prudent.

• Skip that once or twice, and find yourself debating what remaining
clothes you’re willing to leave the house in, and that event gets
pretty firm.

• Out of underwear? Hard event, or an emergency purchase with

next-day shipping.

When your calendar is filled with a mix of hard, firm, and soft events,
with no distinctions made between them, there are three bad

• Looking at your schedule tells you nothing about how much time
you have available. All those calendar entries could be hard events
that prevent you from doing anything else, soft events that make
you needlessly stressed because there’s “so little time,” or firm
events warning that next week could be filled with overtime.

• Mix your hard and firm appointments and you’re relying on yourself
to know the difference on sight. Treat a firm appointment as hard
and you set aside more important things; treat a hard appointment
as firm and you might be late for your own wedding.

• Once you determine whether an event is soft or firm (the hard ones
are usually obvious), you have to respect that decision. Until you get
into the habit of treating your firm time blocks with the same
respect as your appointments, every skipped soft event is an invita-
tion to be cavalier about your firm ones. You have autonomy to blow
off soft events. With firm or hard events, you don’t.

The way to keep track of all this is with different calendars (in the
sense of categories within your calendar app). One of your calendars
holds your hard events. Another tracks your firm events, and a third
tracks your soft events. You can further have several calendars for each
category if you want to be able to divide them by what they’re for—your
kid’s baseball game may not be in the same calendar as a meeting with
your boss, but they’re both hard calendars. Every calendar app allows
you to color code each calendar it contains, crucially allowing you to
assess your week at a glance.

In Figure 5, I show a calendar for someone who doesn’t use many

time blocks.

Note: When I need to show you an entire screen, the text becomes
itty-bitty. Don’t worry if it’s too small to read—the important informa-
tion in those illustrations is the screen layout. When the text matters,
I’ll show you a screen detail with normal-sized text.

Figure 5: A well-formatted calendar in Apple’s Calendar app for Mac,

with color-coding for different types of events.

This sample has hard events in red, time blocks in purple, and soft
optional events in light blue. There is one extra hard calendar for
family events in gray. This is what you want your calendar to look like
when you mostly work from lists of tasks that you haven’t given time
blocks; there’s plenty of time left open for them to flow into. The only
time blocks here are for work needed prior to the Friday morning

Someone who uses many time blocks would have a calendar more like
Figure 6.

Figure 6: The same calendar with more time blocks, and a new
Canceled calendar to track missed time blocks.

The key thing to note: some space must be left available for crucial
tasks on your lists, which take place when no event is scheduled. This
time is also used by anything new that arrives during the day; you
might time block an hour for email, but have a single long reply that
needs more time. In this schedule, there’s an hour open each day and
most of Friday; this is an implicit agreement that not much will get
done on lists of tasks—nearly everything that will be completed has
been assigned time blocks.

There’s a new calendar here called Canceled, and that’s for missed time
blocks. The eye-catching yellow color reminds you it’s skipped and has
to be rescheduled. (I use vibrant and eye-catching colors for anything

that requires action, with less exciting colors for optional soft events
and a few calendars I use to track my time.)

It’s up to you whether you use few or many time blocks. Some people
work better with a full calendar and knowing exactly what they’re
doing; others will only use them for key projects on deadline. I can’t
use them, and not because I don’t want to—after 20 years of trying, I
simply can’t force myself to respect a time block like an appointment.
A time block is usually my cue to work on anything but its scheduled
task. People who work well with this technique should use it, and
others shouldn’t; you should pay attention to what works for you, and
proceed based on your outcomes.

Due Dates and Flags

Due dates are always associated with tasks or projects. An event
doesn’t have a due date, it has a start time. Any work you need to do
prior to that event is a separate task with a due date. Most apps as-
sociate due dates with alerts and notifications and such, ranging in
prominence from “clearing of throat by Disney titmouse” to “car alarm
at 3 A.M.” The right alert method to use is the one that sufficiently gets
your attention, and it’s good practice to vary alert types when you can,
so the most important alerts have the loudest alarm bells. My task app
creates alerts on my phone that are barely noticeable, so when I see
one coming up that’s important, I set an additional timer to go off with
an alarm that wakes the dead.

Tip: I also vary the lead time on my alarms, depending both on what
the event is and what I expect to be doing when the alarm goes off.
A reminder to run an errand may need either 10 or 30 minutes to
wrap what I’m doing, depending on the task, but a soft event may
alert hours in advance so I can decide whether to go well.

Like events, due dates are deceptively complex, and come in hard,
firm, and soft varieties. Hard, firm, and soft mean the same things here
as with events. Hard due dates have consequences when missed. Firm
due dates indicate work that, when not completed, mean more work
later but no immediate consequences: “I didn’t work on my thesis this

week, so I need to do 10 extra pages next week.” A soft due date is an
arbitrary date when you’d like to have something done. Miss it, and it’s
no big deal.

When you have more than a few tasks coming due shortly, you’ll
usually have your task app show all your due tasks, collated from all of
their projects and presented in one list. I’ll call this your Due list.
Sometimes, sadly, you won’t get to everything on your Due list on that
day, and they become past due. Depending on your task app, it could
be a separate list or all piled up at the beginning of your Due list
(which typically defaults to sorting chronologically by due date). I’ll
call it a Past Due list for consistency’s sake.

A Due list has automatic urgency, but some of your tasks without due
dates may be more important. Letting the urgent displace the impor-
tant can cause a serious workflow problem, which you’ve probably
experienced. Many of the things we consider to be due are firm or soft.
The weekly email you send to your group is due Friday, but every so
often you send it out on Monday and no one cares. If you skipped it
entirely, maybe that would be different; you never have, so you don’t
know. All you do know is that when you look at your Due list Friday
morning, there’s a voice in your head saying, “that one can wait.” So
why is it on the same list?

You’ve probably also been in the reverse situation. You’re working

through your Due list, then at 4:45 P.M. you see the thing that must be
on someone’s desk before sunrise. Half the things you’ve already done
could have waited, but now you’ll be eating a microwave dinner before
bedtime because this just canceled your evening.

A hard due date has to have consequences, or it’s not hard. There can
be gradations of that measurement: you might choose to prioritize a
firm due date that leads to a huge workload when missed, over a hard
due date with the minor consequence of sending an apologetic email.

There is a simple solution for this, and it’s counterintuitive for most
people: rarely use soft due dates. A due date is either hard with imme-
diate consequences, or firm with delayed consequences. People use
soft due dates to “force themselves” to get something done by a pre-

ferred date—but you’re smarter than that, and you’ll see through your
own ruse.

It’s grammatically odd to call tasks without due dates “undue tasks,” so
I’ll be calling them Whenever tasks. That doesn’t mean that they’re off
in a nebulous future; some of them may be high priority items that you
intend to get to quickly. Instead of giving them a fictitious soft due
date, most task apps allow you to add a flag or a star to a task or
project—exactly the same way you might flag a message in your email
inbox to give it prominence—and then produce a separate list of
everything you’ve marked this way. I’ll call that your Flagged list.

Note: Some apps use priorities instead of flags, so for example you

might assign a number between 1 and 5. This is similar to Apple

Mail’s option to use different color flags. It’s not a good idea to use

more than one or two higher priorities—if you prioritize your tasks

across many levels, you’ll spend more time managing than doing.

Here are three examples of how to schedule a “do laundry” task (Fig-
ure 7). In the first case, it’s flagged to show up with prioritization
when you’re at home. When you mark it done, your task app makes it
go away for a while, and it’s never actually due. (Every task app has a
slightly different approach for handling repeating tasks, and how you
make them vanish until you need another reminder.) In the second
case, it’s scheduled as a firm task: if you haven’t gotten to it before it’s
due—the consequence being wearing dirty clothing—it shows up on
your Due list. Finally, there’s an example for when laundry might be a
non-repeating task with a hard due date, if your vacation clothes are
different from what you wear at home.

Figure 7: Flagged, firm, and hard due laundry tasks.

You could also mix and match these. For example: a flagged recurring
task reminding you to do your laundry whenever, and a less-frequently
recurring task with a firm due date named, “Do you need to do laun-
dry?” When you see the due task, if you’ve done laundry recently,
immediately mark it done. It’s there as your safety net to “firm up” the
laundry task when it gets lost in the shuffle.

There are two exceptions when using soft due dates can be useful. In
some apps, using a due date is the only way to make a task into a timed
notification or alert. Most of your timed tasks will be obviously soft or
hard: “Do the dishes before Westworld” can usually wait, but “Take
dinner out of the oven” cannot.

Soft due dates with times are also useful when you want to group or
order your tasks by time of day. For example, you could have a list of
all “daily tasks,” ordered by time. I have a bad habit of skipping meals
on busy days, and I don’t notice I’m hungry until two hours after I’ve
become cranky and less efficient, so my daily list has a task due at 4
P.M. named simply “Eat.” When I have already, I mark it done; when I
haven’t, I eat.

Soft due dates should not be used for tasks in the category “this doesn’t
have a due date, but I need to do it as soon as possible.” The problem is
that almost any task can be classified this way. It’s completely painless
to assign a soft due date to such tasks, so this habit creates dozens of
them. It’s extremely painful to have a cluttered Due list.

In theory, due dates are slightly different for pointers than for other
tasks, but in practice they work the same way. A pointer to something
you’ve organized elsewhere has the same due date as the thing it’s
organizing, when you can do it in one sitting—which is usually the case
if you’ve broken it down into small enough tasks. If it will take more
time, the pointer’s due date is however long before the actual due date
you need to get it done on time. Most of the time, these pointers are
hard due.

Recurring pointers can be a special kind of firm due. For example, I

have pointers that say “Go through your new email messages,” and
“Reply to the email messages you’ve marked with a ReplyTo label.”
These are due at a reasonable pace because the longer they wait, the
more work waits there for me. (“Reasonable,” you’ll remember, is
correlated to Define 100% as Peak Sustainable.) But that’s not because
I need to “finish them in time,” since I probably won’t be finished with
email until we all switch to telepathic implants. It’s instead a recur-
rence that balances the time I spend on email with its urgency and
speed of accrual.

Note: Specifically, I have seven different pointers to each of my

seven email addresses—I use each one to separate various roles and
work categories—so I can vary how often they recur based on how
important each one is to me at any time.

A context is a circumstance that has to happen for a task to be avail-
able. It’s usually a place: do laundry at home, or run errands at the
store. But it can also be conceptual: a high-energy time of day when
you do things requiring brainpower, a low-key period when you tackle
the more routine. Or it can be a person: “have a conversation with
Mary” requires Mary to be available.

Contexts act as filters, getting things out of the way so you’re focused
on what needs to happen right now. You probably have any number of
tasks that can be done anywhere, but if you let those mix with office
tasks, you might not see the need to make 20 copies of a report until

you’re home. So at the office you filter for that context first; if you have
extra time after that, you can do some anywhere tasks. But most of
those have an optimal time or logical grouping when you should do
them: When I’m working and I spend a few minutes on my phone, I try
to do something useful rather than catching up on Facebook. When I'm
relaxing at the end of the day, I only listen to podcasts related to my
work when I’m interested enough that it counts double as work and

Note: For more on this topic, see Use Prioritizing Contexts.

The term context is now somewhat out-of-date. As in the above office

example, it refers to a situation that is the only opportunity to com-
plete a task. But that’s a condition more common in the 1980s than the
2020s; it’s probably not the case that the office is the only, or even the
best, place for you to make copies. (Or that making copies is something
you do regularly.) Most tasks, most of the time, can be adapted to
multiple conditions, locations, and environments.

The newer paradigm is “tagging.” A context is a category, and usually a

task can have only a few contexts (or only one) before apps start to get
confused. A tag is a word or phrase related to a task, and in most apps
any task can have any number of tags. So for example, I might have
various tasks tagged “Home”, but some of these are also tagged with
the street of my house. In this case, “home” is a conceptual category
that can include “back at my hotel,” but the street tag is a task that
really requires me to be at home. So when I’m not “at home” when
traveling, I turn off the Home tag and filter out everything that re-
quires me to be where I’m sleeping; when I get “home,” I’ll leave my
street tag turned off because I’m “at home” but not at my house.

As might be inferred, tagging requires more complex thinking than

single contexts, so I’ll continue to refer to contexts in this book. When
you’re comfortable with how they work one at a time, experiment with
layering them in tags.

An Important Context: Waiting For
Many times, you’ll be ready to do something, but instead of not being
in the right place or situation, you won’t have what you need in a
conceptual sense. It’s waiting for something else to happen.
When this happens, it’s in the Waiting For context, which I’m capital-
izing because it’s a key concept for staying on track. A task can be
Waiting For someone else to do something, for you to do something
in a different project (if it’s the same project, it’s sequential after
another task), or for a particular circumstance. I use them so often, I
write them down as “WF [description here],” then assign them the
Waiting For context. Here are some examples:
✦ WF John to get me the numbers I need for the report Friday
✦ WF finishing cleaning out the basement (perhaps the first task of
“repaint the basement”)
✦ WF a spare $1,000 in my discretionary spending to blow on this
toy I want
You review your list of what’s in Waiting For periodically, to see if
anyone needs to be gently reminded you’re waiting, or to check off
Waiting Fors that you’ve already completed but forgot to mark here.
Waiting Fors have a different due date method. The due date for a
Waiting For is the date you need to be reminded you’re waiting, in
order to do the task it’s blocking. When creating the John example
above, “Friday” is the due date of the report, so you might set that to
due Tuesday or Wednesday to have enough lead time for your work
after you receive it. As shown here, it’s always useful to note the
actual due date of the Waiting For item in the description or note.

The Process of Using Your Tools

All of the above can hard to keep straight, especially if you have differ-
ent kinds of organization in different places. Let me present you with a
walkthrough of what your day might look like using your system. This
is only a general overview; details come later, and this structure is
where those details fit.

The landscape of any given day starts with your calendar and the lists
of your tasks. No one starts with blank pages here, as you’re working
from choices you made earlier. Your upcoming calendar has appoint-
ments that you’ve added—the meeting that happens every Thursday
morning, the plans you set three weeks ago to have a drink with a
friend. Your lists of tasks are likewise populated by things you decided
to do, or that arrived with today as a deadline, a while back.

Here’s how to get to work:

1. This isn’t a step, but I’m listing it first because it’s something you
keep in mind from the start.

You’ll have events on your calendar throughout your day—hard

events, firm time blocks you shouldn’t skip, and optional soft
events. During the day, you attend your hard events, you switch
what you’re doing when a project’s time block starts, and you decide
in the moment whether to go to your soft events. You work on your
lists in between events. Picture a river: your events are rocks fixed
in place, your tasks are the water flowing around them.

Your lists affect how you respond to events. If your lists are long, if
your flagged Whenever tasks are particularly important, or if it’s
taking longer to do your tasks than you planned, events can give
way. When the river is raging, rocks lose out to the water. Soft
events can be ignored, firm time blocks can be moved to a future
time, appointments can be canceled or rescheduled. But since you
did the work of deciding which was which earlier—and color-coded
them so you immediately know what each event is now—you do this
in order: soft events go first, firm time blocks with reluctance, hard
events only when absolutely necessary.

2. Your day starts with your task app, specifically a particular list in
your task app. Morning people may want to immediately start
working on something—they go on to the next step. I am emphati-
cally not a morning person, so my first list is a project called “Morn-
ing routine” that gives me low-key things to do while coffee works
its magic.

3. Your Due list is next. Some people do all their due tasks all at once,
while others batch some due tasks in the morning, and then do the
rest of their due tasks in the afternoon. Those people do this step
and the next one in a loop until both lists are completed. It doesn’t
matter if the details of the task are in your task app or elsewhere;
your pointers with due dates send you to where you need to be.

4. Your Flagged list of Whenever tasks are next up. Frequently, your
urgent tasks are due, but your important tasks are here. If you have
enough on this list, it can take you the rest of the day. If you have
these tasks left over at the end of the day, that’s fine—that’s why
they’re Whenever tasks; where you stop today is where you start

5. On those happy days when you finish your Due and Flagged lists
with time remaining, it’s up to you what’s next. Pick a project and
work on its next tasks directly in its planned outline, start on tomor-
row’s Due list as a gift to yourself, pick out a few more Whenever
tasks and flag them, or just call it an easy day.

6. On a daily basis—usually the end of the day—you check tomorrow’s

calendar and Due list to see what you’re in for. (Personally, I also
check the weather.) If you’ll have many tasks, you can cancel soft
events or move firm ones. If you have too many hard events, you’ll
acknowledge it’s a day that won’t see any progress on Flagged tasks,
and you might have to renegotiate some firm or hard due dates.

7. Every week or two, you review your system to see if the progress you
made was what you planned, and make decisions about the next
week or two. The daily adjustments in the last step and this review
are what create the lists and calendars that start your days in the
near future.

Now that you know what these things mean, next you’ll choose the
apps and other tools where you’re going to use them.

Choose Your Tools
Most likely, you’re not only changing your organizational system,
you’re also choosing new tools to use with it. These likely will be new
apps, but new hardware and non-technological items may also be part
of the package.

This is not a difficult process, but it does require planning and fore-

Audit Your Existing Technology

While it’s nice to have an excuse to buy a brand-new iMac Pro, iPhone,
and Apple Watch, most of us go to productivity war with the hardware
we have. Some apps you’re currently using will be eventually aban-
doned after you Run Both Systems Side by Side (Temporarily). (“Both”
means what you’re doing now and the new system, while you transition
to it.) But you may be stuck with some apps as your work and social
obligations require them.

When you choose your additional tools, you’ll want them to integrate
as much as possible with the things you’re already using. For example:
you’ll want your task app to run on your computer or tablet (or both),
and you’ll want its data to automatically appear on your mobile de-
vices. When it’s a good time to buy hardware (now or later), you’ll want
it to integrate with your new system, as well as any old equipment you
may still use (such as if you relegate your old laptop to being a living
room knockaround).

When you’re reviewing your existing technology, it’s a good time to

take notes on past annoying issues (or showstoppers) that led you to
want to improve your system. For example, “I have the best ideas in
the shower and while driving, and I always forget them.” Or, “I’m good
at organizing the information I’ll need next week, but I can never find
anything I put away that I need months later.” These can provide

important information about what to prioritize when choosing better

These are the categories to consider when you’re doing this review:

• Task app and other apps: You’re going to be moving informa-

tion between apps frequently. For example, everyone gets new tasks
in their email inbox on a daily (or minute-by-minute) basis. Just
responding to a particular lengthy email can be a task you have to
manage. Sometimes you manage it within your email app; other
times it’s best to use an integration to get it out of there and into
your task app.

There are three ways to move your tasks into your task app:

‣ Tight integration: Ideally, but rarely, there’s a method of linking

data between apps so that the original is maintained in context.
This method is usually best, when you can have it. For example,
the Daylite relationship-management app lets you link messages
in Apple Mail directly to tasks in Daylite.

‣ Forwarding or copying: Nearly always, your apps will facilitate

bouncing data out of one application and into another. For
example, OmniFocus provides a cloud service that attaches email
you forward to it directly to your OmniFocus database. The
problem is that you’ll lose the data’s original context—for exam-
ple, emails you forward leave their threads behind, and you’ll
have to manually search in your email app if you want to pull up
the original conversation.

‣ Pointers: When a project is perfectly well organized somewhere

else, set a pointer in your task app sending you back to it. If that
planning later needs automated features your task app provides,
you can put it in your task app then.

• Cloud: Usually you’ll use cloud services to move task support

materials from one device to another, so it’s not an integration so
much as a method. But some apps write information directly to the
cloud, which can be useful. Bonus points to apps that use the same

cloud services you’re already using; it’s annoying if most of your
stuff is in Google Drive, but your app insists on Dropbox.

• Non-technological tools: I have clients who started printing out

their calendars 30 years ago, and never broke the habit. Paper
doesn’t need batteries and works out of range of a cell signal. This
might be a small notepad in your back pocket, or a small whiteboard
you keep for ideas in the shower. (Only me? I once made a friend
burst out laughing when I said I had one.)

Consider New Hardware and Devices

I’ve been an IT consultant for 25 years, and it’s always struck me

how many people stick with old equipment because replacing it is

“too expensive.” Of course that’s true if you don’t have the money,

but people who could afford it seriously undervalue the purchase.

A new iPhone costs approximately what the average American makes

in a week. A week is 2% of a year, so that’s the number to use when
equating dollars to time. That is, 2% of an eight-hour workday is 9
minutes, 36 seconds.
Therefore, if a new iPhone saves you 15 minutes a day—which isn’t
much if you use it for hours, rely on it to tell you things when you’re
doing something else, or have to fiddle for an hour to fit things in a
small amount of storage—you’ll see a 50% return on your investment
in one year. (Plus the quality of life it provides in the other 16 hours
of your day, which isn’t included in the cost-benefit here.)
This also applies to buying pricey apps, or even switching between
Mac and Windows, or iOS and Android—if a different tool is better for
what you’re doing, you should at least consider it. I like my Android
phone because it can show me more information on my home screen
than iOS; I also have an iPhone because there are two or three apps
I need in my pocket and can’t have on Android.
A special case: if you have to use both Mac and Windows, it compli-
cates your selection of apps substantially. More on this on this book’s
blog: Cross-Platforming Mac and Windows.

A Good Reason to Keep Work Separate
Regardless of your preference for how you mix your work and every-
thing else, there’s a privacy issue to keep in mind. In the United
States, any data that lives on work-owned hardware, or passes
through work networks, can belong to your employer. Specifics
depend on the situation, but vindictive employers have sometimes
alleged ownership of their former employees’ or contractors’ intellec-
tual property, purely to cause them legal difficulties.
The easiest way to avoid this: keep organizational data on hardware
you personally own. Buy your apps with your own money. Use public
cloud services instead of a network server. No matter how much work
data you keep in your system, you should regard it as private and
personal. You may make notes to yourself that aren’t for a wider
audience, or have professional goals that don’t quite align with what
your boss would prefer.
And for Pete’s sake, speaking as a guy who has run corporate email
servers, don’t send or receive personal data at your work email
address. You wouldn’t believe the things I’ve seen on my servers—
and sometimes, it’s a legitimate work requirement for people like me
to go spelunking through it. It’s not only your boss who can see your
stuff; it may also be the guy who fixes your printer.

Select Your Task App

I’ll be honest: here I’m hitting a difficulty. There are literally hundreds
of different apps you can use, and each one of them influences how
you’re going to work with your system. Listing all your options would
be a 500-page book that I’d need to update weekly.

Your choice of apps truly matters, especially your task app. Apps that
are too complex increase your planning time and work friction. Apps
that are too simple drive you insane because you’re constantly fitting
yourself to its methods. When apps are missing a feature you need,
you’ll probably invent a workaround for it, which will be cumbersome
to manage.

Most people will work best with a relatively powerful task app, other
apps and tools that are simpler to use, and various collection points. I
live in OmniFocus, but I also use Google Tasks and Google Keep as my
most frequent collection points and for simple organization—the
advantage of using a simpler app being that it’s usually faster. I also
organize and collect in a dozen other places.

Note: Many people use their email inbox for organization. This is an
awful practice—you’ll look at and think about a message several
times before actually doing anything. Organize it elsewhere instead—
which can be as simple as “drag to the ‘Urgent,’ ‘Later,’ or ‘Needs
Reply’ folder,” if you have pointers in your task app for each.

Unfortunately, there’s no way around some trial and error. You won’t
know every feature you need until you’re working and discover your
task app is lacking one. You’ll be able to avoid obvious mistakes if the
app has a trial period, but that might not be enough time. (Over the
long run, you’ll solve this problem by iteratively trying out new tools.)

This section cuts that Gordian knot with the following approach:

• First, I present a menu of features, from which you should choose

what’s necessary, what’s desirable, and what you don’t think you’ll
need. Use these as guidelines when you evaluate apps.

• Then I touch on major categories of apps (roughly ranging from

simple to complex), which will help you narrow down what might
work best.

• As we go, I show you what a common app in each category looks

like, so you can get a feel for what seems attractive.

Web content: I’ve evaluated many productivity apps (over the years
for my own system, and again for this book) and written about the
better ones in various categories and for different platforms (Mac,
Windows, iOS, and Android).

You can get started with my list if you need suggestions. If those don’t
work, a Google search should point you in the direction of app websites

and third-party reviews. Between the time this is written and the time
you read it, there will certainly be newer options, as this will likely
already be true 12 hours after publication.

Features to Look For

Every app’s website is going to tell you how it’s the One True Organiza-
tional app. There’s no such thing, only the one that works pretty
darned well for you. As you review these features, don’t try to make a
master list of everything you want; instead, pick out a few that are
important to you, and make a note of what would be nice to have.

• Works on your devices: Perhaps the most obvious, but let’s not
skip it. It’s got to work on what you own, unless you’re buying
hardware specifically for it. Web apps, and apps that have a web
component, can be a workaround; most web apps that don’t work
well on a mobile device have a specific app for that platform.

• Rapid collection and review: You want to get new ideas out of
your head quickly enough that they don’t break your workflow, and
have immediate reference access to your lists. On a computer, that
usually means hotkey access to instantly bring up a window. On a
mobile device, that’s an app that launches with no delay from the
dock, and ideally has iOS Today View or Android widgets.

• Repeat and due flexibility: You might want a task every month
to get a haircut, but it’s better when the clock doesn’t start ticking
until after your last one. Applications vary greatly regarding ways to
set up due dates and repeating tasks; it’s always nice to have more

• Context flexibility: Simple apps won’t include the concept of

filters and contexts at all. Complex apps can make them very fiddly
to use. Look for apps that allows for rapid context setting and
filtering. Almost always, tags are more flexible than fixed contexts,
since once you’ve created them, you can mix and match them. (Such
as a task that’s “Home,” “On my iPad,” and “When Low

• Mobile reminders: You want important items to jump up and
down, waving flags at you—but no more often than you need. This is
usually best on your phone. Or a smartwatch, which is excellent for
this, as alerts can be checked and ignored with a glance. Also useful:
reminders that trigger when you’re in a particular place, not at a
particular time. (If that feature isn’t in your task app, you can get it
with built-in reminders on your phone.)

• Sharing and collaboration: When you want other people to be

able to read selected lists, or suggest new tasks to you, sharing and
allowing editing of a walled-off portion of your system can be
helpful. No one gets to see my OmniFocus database, so I create
pointers to documents I can share, and do that organization there.
Some apps provide ways to do this internally.

• Team features: There are methods with self-management apps to

handle delegation, and other issues regarding working with other
people, but sometimes you need everyone working from the same
playbook. Sometimes, you can point from a personal task app to
projects living in team apps. But if you do this frequently, you may
want to simplify by living in a team task app.

Keep in mind: when your team task app is owned by someone else,
so is the data that lives there. Keep everything private in personal
apps that you own. It’s up to you whether your team app or your
personal app is your task app; either way, use pointers in the first to
point to the other one.

Note: I frequently have to add client-specific places to my system,

when they use a tool I don’t and I have to join them there. Whenever
this happens, I set a pointer in my task app to check them, and
delete it when I stop using their tools.

Kinds of Organizational Apps

The following are key applications, organized by increasing complexity.
These are popular, and with the exception of the simplest these can be
taken as general recommendations. But unless you’re extremely

pressed for time and want to Get Started with Your Task App immedi-
ately, you should consider other options that are a better individual fit.

Reminders and Google Keep: Too Simple

Apps like Apple’s Reminders (iOS/Mac/web) and Google Keep (iOS/
Android/web) are what most people use, with the methods they
learned in high school: make lots of flat lists, maybe with a morning
brainstorm of things to do that day. Few people in this book’s audience
will be happy using one of these as their task app, as shown with how
such a system might work in Figure 8.

Figure 8: An example collection point in Reminders, which is all it

should be used for.

Prior to iOS 13 and macOS Catalina, any full-fledged system using

Reminders as a task app had a bazillion lists in the sidebar with poor
organizing tools. This has improved in the currently shipping versions
on Mac and iOS, but other issues have arisen (such as the fact that
iCloud sharing your Reminders requires Catalina if you’re using iOS
13, even if you’d rather stick with something more compatible with
other apps). In the first version of this book, I told all readers to avoid

Reminders as a task app; now I’ll say that it might work for some
people but few of them read productivity books like you’re doing right
now. Its best use case: use it to find out what features you instinctively
look for that aren’t there, then use that list when you shop for better

There is, however, one excellent feature in Reminders on iOS, or

Google Assistant on Android: they store reminders you dictate to your
phone or your Apple Watch, and hence serves as a very convenient
collection point. With Reminders, you can pull them up on your Mac to
copy them into your task app. On Android, you’re out of luck unless
you use a service like IFTTT to duplicate them elsewhere.

Stacking Simple Apps for Added Control

A caveat to my recommendation that “the Reminders app is too
simple”: it can be used in conjunction with the Notes app (iOS/Mac/
web). Notes, oddly, has better list management tools than Reminders
does. For example, you can make nested lists in a note, and with this
clever trick from StackExchange you can even link some text to an
entirely different note. Some powerful information management can
be done this way.
By dividing your data between Notes and Reminders, the combination
could work for some people. In Notes, you would store brainstorms
and lists of things you’re not yet doing; the only lists in Reminders
should be what’s on deck. When you finish what’s there, grab the
next tasks from Notes to paste into Reminders, and so on.
That said, there are many features in more powerful apps missing in
Notes. As Josh Centers points out in Take Control of Notes, there isn’t
even a tag or context feature. (Nor is there one in Reminders aside
from preset smart lists.) The new features in iOS 13 and macOS
Catalina change my recommendation from “don’t use these as your
task app” to “if you’re already using them and haven’t had a problem,
maybe they will continue to work for you.” Not meant as high praise.

Things: Simple and Decent

I’ve used Things only to review it for this book, but I’ve listed it as a
categorical example because I’ve heard it mentioned often as the best
alternative when other apps are too complex (Figure 9).
Figure 9: The Things interface is simple and clean, with some

hidden complexity available in an intuitive interface.

Things is based around a set of special lists, a list of projects (starting

in the middle of the left sidebar), and tasks which can have additional
structure such as notes and subtasks. Tasks can have due dates, or you
can manually add them to the Today list to do a morning brainstorm.
This is effectively equivalent to flagging tasks in other task apps, but
has the drawback that it’s a manual method. Automatic collation of
flagged tasks is better.

Things integrates with your calendar and notifications, so you see

everything in one place. Tags allow you to set single or multiple con-
texts, or create other methods of organization. The software is nicely
cross-platform in the same way that you could get a Model T in any
color so long as it’s black: so long as you only use Apple products, there
are apps for Mac, iPhone, iPad, and Apple Watch.

Other software in this category: nearly all apps I’ve seen in the $10–20
range on a computer, or a $0–10 range on a mobile device. Some of

them are closer to Reminders, and a few allow for some added com-
plexity, but I haven’t yet seen a suitably powerful app for cheap.

Before You Decide on Simpler Software

If this level of complexity looks like it’s your speed, consider this

before you decide:

✦ Read the section about OmniFocus: Powerful But Complex, to

make sure that simpler software is the better choice.
✦ The most likely way this kind of software will fail for you is a
crucial missing feature—and some of those needs might not crop
up until later. It’s a big deal to be able to export your data cleanly,
because if this happens often, you’ll want to jump to something
with more bells and whistles.

Trello: Visualization for Teams

Trello (iOS/Android/web) eschews the normal task management
interface in favor of a highly visual one (Figure 10), called “kanban.” I
mention it here because it’s nearly alone in its category, and it’s the
simplest software I’ve ever seen that provides excellent team manage-

Figure 10: One of the Trello “Inspiration” boards that provide

examples for how to implement your own boards.

Trello is based on a series of boards. Each board contains lists, each list
contains cards, and a card can have an arbitrary number of checklists,
labels, and comments. Sharing is done at the board level and the card
level. Board sharing indicates who can read it or edit it, while card
sharing sets up notifications for any activity with that card.

The natural level at which to assign projects is with a list, while using
boards to determine sharing groups. In this case, a board would be
assigned to a company team, or to a particular client with whom you’re
sharing it. But that may be too flat for your projects, since you can’t go
too much deeper than that. In which case, create a board per project to
give you one more nesting level.

You can’t see two boards side-by-side unless you arrange multiple
browser windows, so each board lends itself to seeing a group of lists in
parallel. That leads to a second Trello limitation, as you can only see as
many lists as you have horizontal space on your screen. You can scroll,

but as Trello is more visually oriented than outliners, it’s less than

Trello is an excellent app to use in addition to your task app, for people
who have occasional need for shared task management. It might work
as your task app if you end up spending most of your time there
working on team projects, but you shouldn’t attempt that until you’re
thoroughly familiar with its features and limitations.

Note: The Trello Inspiration S.T.O.P. Board has some interesting

ideas for implementing personal planning. Scroll to the far right of the
board for step-by-step instructions.

OmniFocus: Powerful But Complex

I think software with the complexity of OmniFocus is a likely fit for this
book’s audience. But here I’m making suppositions about what you’ve
used before you got here, and the likely needs of anyone reading a book
about productivity. If you don’t think it will be too complex, it’s an
excellent option (Figure 11).

Figure 11: The project view in OmniFocus, where you’ll spend most
of your organizing time, working on tasks when you need to see their

OmniFocus comes in two flavors and two pricing plans: a well-featured
normal version, and a Pro version with additional options that are
highly useful for creating more focused lists. You can purchase these
apps outright for Mac or iOS, or a you can buy a subscription service
that licenses the Pro versions of both and adds a web interface to your
data with a smaller feature set. (There’s also the FocusGTD Android
software, unsupported by Omni Group, which also has less functionali-
ty but works well for working from your tasks.) Basically, if you’ve
already purchased OmniFocus or you hate subscriptions, you can keep
buying upgrades and own them forever; for new customers, a subscrip-
tion is likely the better option. Regardless of subscription status, the
Omni Group offers a free (and reliable) cloud service, making it a snap
for all your apps to share the same data.

OmniFocus is highly customizable in showing your lists, but you’ll

probably start with a Forecast view for working with your due tasks
(Figure 12).

Figure 12: The forecast view in OmniFocus, showing you past,

present, and upcoming due items. Work off your Due list here, then
switch to flagged with your remaining time.

OmniFocus works well with the productivity system I recommend—not

surprising, as both share similarities with the Getting Things Done

methodology (but with extensive variations). The top level is a list of
projects, which can be grouped into folders for easy reference and
organization. Projects have tasks, and tasks can have infinitely nested
subtasks, so there’s no limit on how deep your structure can go.

Every task can be assigned any number of tags, and can repeat in a
variety of ways (such as every second Thursday, the 15th of the month,
or two weeks after you last completed it). You can also assign start
dates to any task or project, so you’re never bothered by them until
then. Projects can be put on hold, dropped, or completed. The last two
store projects in an archive but remove them from your lists, while on-
hold projects retain visible tasks, but are set to unavailable.

Finally, you can flag tasks and projects. Any subtasks they have are
marked with a hollow flag (indicating it’s inheriting its flagged status).
Flags are the easiest way to go through a list of things you want to get
to, and select several to complete in an upcoming period until the next
time you review. You could also organize by grouping them in a partic-
ular project or list to indicate priority, but it’s easier to Use Prioritizing
Contexts and leave tasks in their original place.

OmniFocus is highly customizable, and you can turn off the display of
some features. But you’ll always see everything when you pull up a task
inspector (the right sidebar in the screenshots above), so some of its
complexity is “always on.”

Note: I’m normally a fan of diving into software and learning by

doing, but in the case of OmniFocus, reading the online help is a very
good idea.

OmniFocus is my task app, and my key feature is how flexible it is for

rapidly entering new tasks. A hotkey on the Mac, or a button that’s
always available in the iOS app, brings up a window for task entry
where you can set the project, start and due dates, and context imme-
diately. If you don’t set the project, it goes into the OmniFocus inbox.
If I’m working on something, and an email or stray thought hits my
radar, I toss it into OmniFocus and am back on task in five seconds.

That said, this app has limitations and frequent annoyances. I have to
use pointers more often than I’d like, because a day’s natural flow
creates a branching mind map (or data soup) that can’t be recorded
directly into the OmniFocus outline. In theory, during my weekly
review I should take these documents and process them all together
into my task app; in practice, this would sometimes make a review last
the entire weekend and I don’t have that time to spare. I wish OmniFo-
cus had a paradigm for dealing with this, because while my pointer
methods, it triggers my psychological limit of feeling too scattered.

Another major drawback: OmniFocus has no capacity for sharing

sections of your data publicly, and export options are limited in terms
of making pretty documents. When I have to circulate project informa-
tion with other people, I’m frequently in different software, or I’m
double-entry bookkeeping in OmniFocus for organization, and some-
where else for sharable documentation.

The primary reason people start with OmniFocus and later switch is
complexity. There’s an awful lot of it, and frequently it’s not clear how
to adapt particular features to suit your workflow. When that happens,
consider cracking open the online help again—Omni Group writes
some of the best docs in the business—or check out the excellent
OmniFocus forums to see if someone has already solved your problem.

Note: There’s another paradox of choice here. In simpler software,

you know you can’t implement a workflow within its limited features,
so you don’t try and it’s not frustrating. OmniFocus always seems to
have a way, if only you could figure out how.

Daylite: Very Complex Company-wide Management

Customer Relationship Management software (abbreviated CRM) is
the type of app to use if you need infinite complexity, team tools, or
business-related functionality. The downside is that such software is
horribly complex—it’s not uncommon for businesses to hire consul-
tants to build custom workflows inside these apps, and some nearly
require such an investment by being too difficult for the average
person to use. Daylite for Mac is my top pick because it’s an excep-

tion—it’s very useful out of the box. But it’s still much more complex
than anyone who isn’t running a business needs. (I’ve used CRM when
I’ve run startups and small businesses. When I’m only consulting, I
don’t need it.)

In a CRM, you don’t necessarily nest your projects and tasks; instead,
nearly everything in Daylite can be linked to anything else, so instead
of a hierarchy you have more of a spider web. For example, if you
wanted to document everything about your business operation, you
could start with a list of companies that are either clients or sales
targets. Each of these would connect to people working there; if they
move on, you disconnect those links and keep the contacts, linking
them to their new companies. Any of these can be linked to projects,
tasks, and opportunities (a category of project for sales possibilities),
each of which can have their own links to other projects and tasks.
Then you can throw events into the mix, and custom data types like
places and expenses.

Here’s one of the many different views you get of your data in Daylite
(Figure 13). In the left sidebar, there’s a list of built-in views of
various kinds of data, and you can add more custom layouts. This is a
Contacts view, so the second column is a list of people. The middle
pane is the detail of the selected person. Finally, on the right, you get a
list of all other events, tasks, and other items linked to her.

Figure 13: The contact view in Daylite.

So if you liked, you could express the following entirely with links
between data without writing it out: “Had a meeting with Joe and
Anna from BigCorp, about the possibility of their web project, at the
nearby Panera Bread. Spent $18.90 which I need to expense. Follow up
on Tuesday with an email, and next week with a phone call.” Then you
could create separate lists of your tasks, your expenses, or even where
you were last month if you want a memory jog.

All the things you do before, during, or after a project or opportunity

can be set up as a recurring pipeline, which is a template of tasks you
repeat for any given situation. This is also possible with other software
using workarounds, but Daylite’s built-in approach is much more
manageable if you have many pipelines or templates.

All this is available to teams, or even to entire companies, as shown in

Figure 14. When five different people talk to the same contact, they
can keep running notes on those interactions all in one place, or as a
history that’s connected to both the project and the contact. All such
data in the app can be shared with everyone, or only to people with the
right permissions. (But if you’re not the boss, the things you don’t
share might get shared for you with your managers.)

Figure 14: Detail of the team view in Daylite, where colleagues and
managers can track where everyone stands in real time. This is a
cropped view of a full screen for legibility.

Salesforce is probably the most well-known CRM software, but it’s

exceedingly complex, and frequently requires custom programming.
But there’s very little it can’t do if you bang on it long enough with a
hammer. It’s a web app, available everywhere.

Over the years, the other CRM web app I’ve heard about most often is
SugarCRM. Originally, you could download their software and run it
for free on your own server without official support, but SugarCRM
abandoned that option with their 7.0 release in favor of a Salesforce
subscription cloud model. But you can still use SuiteCRM, a supported
“fork” of SugarCRM 6.5; it’s free if you run it yourself on your own
hardware, but it’s paid if you use their cloud service or need technical
support. It’s available for Windows and Linux (and after jumping
through many hoops, Mac), but fair warning—it’s the kind of software
where you’ll want “system administrator” in your past experience to
run it yourself.

Web content: Reminder: the apps listed here are very good, but

they’re not blanket recommendations. You should look around a bit

before deciding. Start with my descriptions of other apps.

Evaluating Your Chosen Software
If this is your first time setting up, you may make a choice that turns
out to be less than ideal. You won’t want to switch task apps later, as
new software always requires extra work—but at the same time, right
now you have little information about what software styles are best
for you. Alternatively, new productivity software is released frequent-
ly, so you might learn of a new option you’d like to check out.
Suggestions for splitting the difference:
✦ If you run into problems, your default should be to stick with what
you’ve got—but not obsessively so. Make a list of problems you’re
having, and highlight the ones that you run into frequently.
✦ Check the support for the software. This could be a support email
address, online forums, and perhaps even—horrors—a manual.
Find out if there are any workarounds for the issues you’ve had.
(Do this before you spend much time coming up with your own,
especially if there are forums. Almost certainly, you’re not the first
person with this problem, and it’s been solved.)
✦ If you’re left with any dealbreakers, it’s time to switch. Review

your options, and Get Started with Your Task App again (on the

next page) to move from your current system to the new one.

You now have your task app picked out—it’s time to move in.

Get Started with Your
Task App
All along, you’ve been laying important groundwork for making use of
your tools. So in truth, you “got started” several chapters ago, since
without that preparation you’d run into much bigger difficulties when
it came time to start launching apps. But you usually only have to do
that once—while this “get started” is something you may come back to
when you Fail Successfully or Consider Everything.

The things you do when transitioning to a new system are similar to

what you’ll be doing as ongoing processes after you’re using the new
one. The differences, and they’re big ones:

• When you start, you have a lot of things to move in, and this takes
time. Once you are migrated, working in your new system should
take less time than it does now. It will likely be faster than your old
system too, but if not, you’ll get more bang for your buck out of it.

• You might be learning new software. It takes time to turn all those
menu commands and buttons into muscle memory.

• On top of that, you’ll also be using your old system for a while
longer, because your life can’t go on indefinite hold just because
you’re getting organized.

No two ways around it: this takes more time than just sticking with
your old system. But once you’re done and using your new system,
you’re going to feel more on top of things than you do now, and when
you work on something, you’ll know that’s the right thing to be doing
then. Psychological studies show that people who are focused on their
work in this way are happier. It may take longer for you to improve
your productivity (as you define it), but this benefit should be a nearly
immediate reward.

Document Your Old System

I’ve already made frequent mention of your “old” system: what you’re
currently using that you want to improve upon. This probably caused
great mirth among those readers whose “system” consists of an email
inbox with 8,000 messages, hastily scribbled lists of things to do, and
30 pounds of paper they carry around in their shoulder bags.

Whatever it is, you already have a bunch of places where you jot down
organizational ideas, store reference materials, and make notes about
what you might want to do in five years. If you’re rather disorganized
now, you might have many places where you do this. You should figure
out what they all are, virtual or otherwise. Don’t forget the stack of
papers and mail on your desk (or dining room table, if you eat in the
kitchen), the voicemail and voice memos you might have recorded, any
documents in the cloud that aren’t on your devices, information and
tasks stored in Slack or similar work chat environments, or the widgets
and receipts you’ve jammed in your glove compartment.

Finally, include your calendar. It’s not uncommon to stick with the
same calendar you’re already using; that makes the next steps easier,
but it’s not required.

Don’t do anything with those places yet. It’s enough to have a list of
them. Spoiler alert: you’ll be working with this shortly.

You’ll be replacing a fair number of these places with your new system,
but perhaps not all of them. The glove compartment is a nifty place to
quickly stash things you can’t deal with until you get home. That’s why
you’ll use pointers in your new system to check it periodically for
anything there that needs attention.

Get Used to Your Tools

You’re almost certainly using new software, and maybe a new gadget
or two, as you’re getting started. Some folks take to these things as if

they’re shiny new toys, while others enjoy the process about as much
as blisters while they’re breaking in new shoes.

Your instructions are slightly different depending on which is you:

• If you’re not a technophile, learn your new tools just enough to

reduce friction when you start using them. It’s disruptive, when
you’re writing a document in a new word processor, to suddenly
have to figure out how to use that footnote feature you’ve never
touched before. The same thing applies here: know enough of the
basics of your software and tools, such that using them isn’t a
constant process of checking the online help.

• But if these are shiny new toys, you might fall into the other trap:
spending all your setup time fiddling with everything to make it
“perfect.” You pick up your phone to set up an app, and 30 minutes
later you’ve spent that entire time setting up the feature that down-
loads NASA photos daily for your wallpaper.

Note: Getting distracted by something else is one of the aspects of a

derailing process called “yak shaving,” the avoidance of which is
discussed in Manage Your “Yak Shaving”.

There are generic tricks for learning new software, which I recommend
if you’re not happy about adopting new tools. New-toy people should
try to limit their app setup to only these steps:

• Click on every menu, and read the menu items carefully. Some of
them will mention features you didn’t know exist, and the way
menus are written can jog your understanding of when you would
use it. (I discovered way too late that TextEdit, the basic Mac text
editor I’ve used for years, has fine-grained paragraph spacing; it’s
not obvious but it’s buried in a submenu.)

• Skim the table of contents in the app’s built-in help, on its support
website, or in the accompanying PDF manual. This gives you a
sense of the terrain for the software, and will probably reveal fea-
tures you’d never find by clicking around.

• Read only the parts that relate to things you’ll do immediately, and
skip what seems esoteric or less useful. But do make a quick note of
what they are, in case you need them sooner than you think.

• Open the app’s settings or preferences window, and note what

options are there. As with the table of contents, you’re mainly
acclimating to what the options are, whether or not you’ll ever use
them. You might find yourself coming back here if something about
the software is immediately annoying. If you see anything obvious
that you know you want, go ahead and flip that switch. Don’t do this
if you’re currently uncertain what it does.

Pick a Review Period

A review period is the formal phrasing for “figure out every Sunday
what I’m going to do this week.” It’s bookended by recurring tasks you
complete with your task app: updating your projects, moving things
around, sanity checking your due dates, and other maintenance. At the
beginning of every review period, you decide which things you want to
accomplish between then and the next review—I’ll explain how shortly.

The default timing for this is a week or two, since most of us have
handy weekends when we can set aside some time to do this. Exceed-
ingly busy people managing multiple projects may prefer to have
shorter review periods to handle the extra complexity. The more often
you review, the less time each one should take.

I don’t recommend less frequent reviews, at least not to start. Review-

ing your system is an unfamiliar behavior, so get into the habit first by
checking in frequently. Later on, you can lengthen your review periods
if you prefer.

If you find that you’re not on top of your commitments as much as you
like, your review period is too long. Reviewing your system is also how
some of it gets sufficiently lodged in your head to have a sense of the
big picture.

Set a Planning Window, if You Like

This one’s optional. A review period is too short to tackle any major
project, only the parts of it that fit into it. On the other hand, New
Year’s resolutions are usually troublesome because they’re too long: for
half the year, you think you have plenty of time to get to it, and the
second half, you realize you’re as busy as when you put it off.

A planning window is simply your scope for how far in advance you
want to have things organized, with a rolling start date set to “now.” If
it’s March and you have a three-month window, anything you intend to
complete (or at least start) by June is in the scope of your system, and
should get some planning and organizing. Anything beyond June is
Somebody Else’s Problem, specifically, the problem of future-you
who’s going to get to it later. A planning window is a deliberate deci-
sion to have a cutoff, for things too far in the future to worry about.

Note: This only refers to planning out the project. If information

shows up on your doorstep for future projects, by all means, have a

place to put it where you’ll see it later. This can be a note in a task

with a start date when it becomes relevant.

Create Your Mandatory First Project

You already know what your first project is, but it may not have oc-
curred to you that it is a project. You have a new planning system. The
first thing to plan with it: using it. In my industry, we call this “eating
your own dog food.” It’s a good practice.

Note: If you settled on software that absolutely won’t work for you in
practice, you’re going to see the edges of that problem now. That’s
good, as if you’re going to switch, the earlier, the easier.

Make a new project in your task app, and add a task to it: “Review the
tasks and projects in my task app.” Set it to repeat with a due date at
the end of every review period. This is a firm due date, as it’s not a

fixed deadline, but the longer you go without, the more likely it is you’ll
have productivity management problems.

What should you name the project? Depends on your personal style.
You could create one project where you store all your “meta” tasks
(that is, the tasks you perform in order to manage your tasks). I prefer
to use one master list where nearly everything that recurs is stored:
“take out the trash” is on the same list as “review my system,” but has
different contexts, start dates, and repeat frequencies.

Run Both Systems Side by Side

Switching from your old system to a new one all at once is an excellent
way to drop important projects on the floor and miss your deadlines. If
you do this, you’re relying on your new task app before you really know
how it works, and you’ve shut down anything in your old system that
kept you on track. Instead, you run them both simultaneously as you
gradually migrate from the old to the new.

Setting Up
Add a recurring pointer for every place you identified in Document
Your Old System. Your old organization and lists are no longer where
you add new work, but instead are collection points for things to add to
your new system. The pointer is a prompt to add things from each old
place to your new one.

For places with lots of stuff, don’t try to do it all at once. That’s why
you’re using recurring pointers to tackle this. When you work on
moving your projects and tasks, do it until you have to do something
scheduled, get bored, or get too brain-fried to usefully continue. This is
also an excellent time to Use Sprints, so you don’t have to hit exhaus-
tion before you stop.

However, one thing you do want to get to quickly is your calendar. If

you’re changing to a new app, you’ll need to move your data over. If

your calendar is stored locally, look for an option in your old app along
the lines of “export a calendar file” or “.ics file”; that’s the lingua
franca of all calendar apps. Your new calendar app will have an import
feature. If you keep your calendar in the cloud using a service such as
iCloud or Google Calendar, just point the new app at the same location
as the old.

Either way, when your data is where it’s supposed to be, your task is to
consider every future event and decide whether it’s hard, firm, or soft.
Add at least three calendars for these categories—you can use more if
you also want to say something like “Work Appointments” for hard
events and “Family Chores” for firm events at home—and change
upcoming events to one of the new ones. “Upcoming” is defined as
“however far you need to plan ahead and know how much time will be
available.” Don’t forget to share your new calendars with whomever
else should see them.

Note: In most calendar apps, double-clicking on or tapping an event

opens a details window, where there will be a drop menu or such to
change the calendar. Google Calendar has a different approach on
Android: copy the event to the new calendar, then delete the original.

As for everything else, it should be fairly straightforward once you’re

used to your new task app. When you get to a project in your old
system, add it to your task app, then flesh out its component subpro-
jects and tasks. If your old system stores documentation you need for
the project in an app you’re dropping, the easiest way to do this is to
print it as a PDF—most task apps allow you to attach that file to your
project directly in the app. Otherwise, create a pointer to the document
along the lines of “If you need to review completed tasks, go
here.” (Also what you do if your old system is on paper which you don’t
want to scan or take digital photos.)

Finally, cross out the project in the old system, and replace it with a
pointer to your new one. You may still be using your old system as a
starting point for a while longer; this pointer tells you to work with it in
the new place. Continue using your old system for other projects until
you have a chance to migrate them.

Once you have everything in a place well documented in your task app
or elsewhere in your new system, keep the place if it’s an ongoing
collection point that you’ll continue to use. Add pointers in your task
app to make sure you go back to it regularly. Abandon places you will
no longer use, and delete any pointers you might have created in your
task app that send you there. Then do something with those places to
make sure you no longer use them; for example, if you have a stack of
to do lists that you used to regularly consult, file them away some-
where hidden so you’re not tempted to use them again.

Note: Or burn them. It’s very satisfying.

Creating granular and specific tasks is also a habit you can start now:

• Bad: “Once a week, work on moving my stuff into the new


• Good: “Spend 30 minutes taking pictures of the papers on my

desk, storing those for reference in the cloud, and planning their
followup in my software.”

Set it to due every so often, then deferred for a few days each time
it’s done. Duplicate this task to set it up for your other places with a
little editing, each with its own instruction for you. Make more
important places recur more frequently, so you’ll get through them
faster. (You’ll see this kind of task again, where you tackle a moun-
tainous task with repeated but brief effort, when you Use Sprints.)

Give Special Attention to the Urgent

In addition to having regular tasks to move your old stuff into your
new system, there’s one more reason to go to your old places: as
quickly as possible, you want to look where anything urgent or due
soon is hiding.

How you do this will depend on how you used to track these. It’s
probably not necessary to scan anything more than a month or two
old—unless, of course, somewhere in there is last year’s reminder to
pay that annual bill that is consequential when missed.

If you know there’s a place that you won’t finish cleaning out for a long
while, and something in there might bite you if you aren’t reminded of
it, give it the fastest review you can for only those things. Don’t get
distracted and make it a regular clean-up. You’ll get to that on the
schedule you’ve already created.

If you can’t do this all in one sitting, it’s another recurring task. Set it to
recur quickly enough that you’re minimally worried about where all
these items might live. If you’re still concerned that won’t be soon
enough, do all your urgency scans first before you move anything else.
This is less efficient (since you’ll be reading every old list twice), but
might induce greater peace of mind.

Put New Stuff Only into the New System

Here’s how you “naturally” migrate over time, in addition to anything
you’re doing to move old stuff to new places. Anything new that lands
on your plate gets organized in your task app (or someplace your task
app points to), or stored in a collection point for later. No exceptions.

If a new item arrives with urgency attached, and you haven’t yet
figured out how to make your new apps and gadgets fire off sufficient
alarms, do so now. You can’t let “this is really important” be your
excuse to backslide. Every habit you already have is trying to pull you
back to what you used to do. You’re taking on this transition for a
reason. Allow yourself to use the old habits for “important” things, and
pretty soon you’ll be in the old system again, or in a state of permanent

Painful. Don’t do this.

Point Everything to Everything Else

This is how you keep everything straight while you’re mid-transition.
Set up a pointer in your old system to tell you to look at the new one,
then set more in your new task app that point you back to the old one.
At first, you’ll be using the old system’s pointers much more often, but
over time your new task app becomes a more useful starting point.

When you find there’s nothing worthwhile in the old system any
longer, congratulations, you’ve migrated.

Now that everything’s in place, let’s go through how you’ll be using it.

Work with Your System
Now that you’ve got either a working new system or one you’re migrat-
ing into, it’s time to review the steps you take in order to make it
useful. Some of it will be familiar from when you set it up, others are
new, but none of them should be particularly surprising.

Store Ideas in Collection Points

The point of having enough collection points is to be able to get things

out of your head quickly. Stray thoughts, reminders, and communica-
tions happen every waking hour, and most of that time, you’re already
focused on something else. Many of us are in the habit of taking “just a
few minutes” to deal with those immediately.

That’s almost always a bad idea. Anything that suddenly pops on your
radar hasn’t been thought through, so you’re not in a position to know
if it’s truly a three-minute task. (Many of these have hidden prerequi-
sites, which sends you into time-consuming “yak shaving” territory;
see Manage Your “Yak Shaving”.) What you’re currently doing, you’ve
already decided to do now. And remember: switch tasks, and it will be
20 minutes before you’re in the groove. My guess is it’s even longer if
you’re trying to keep both things in your head at once.

Instead, get these interruptions (whether they’re in your office or in

your brain) out of the way as soon as possible. You have to make time
for time-sensitive interruptions, such as someone dropping by your
desk, or a phone call when you’re not able to let everything go to
voicemail. Some email and text messages also qualify. Go ahead and do
those—you have no choice. But the tasks they generate may not be as

Everything else, you stash for later, and you do that by putting it into
one of your collection points. Here’s a task I created three minutes ago
(Figure 15).

Figure 15: The quick capture feature of OmniFocus.

My trigger was when I started playing my “writing music,” and the

headset that worked perfectly fine 20 minutes ago started playing
mono in my right ear. This could have been entirely distracting;
headphones are on sale next door to where I’m writing this. Instead, I
fired it into my task app. By setting it to the “One-Offs” project, it skips
the OmniFocus inbox and lands where I need it to; no further action

Ideally, some of your collection points will allow you to set some
details about your tasks when you record them (as I did in the screen-
shot, by setting its project and context). But that’s rarely possible; most
of your collection points won’t handle that organizational data. When
you have several options, use the best one; on my Mac, it’s 15 seconds
to store a task with the OmniFocus quick capture window, but only 60
seconds to switch to OmniFocus and do it right when I need to add
more details.

Note: The most important data to set when you store something is
its due date. A due task waiting in a collection point still shows up on
your Due list—but only if you store it in your task app, or point
yourself to look at due tasks in other places frequently.

What to Keep in Your Head
Some people are good at putting things away in their heads and
reliably retrieving them later. Others, to put it mildly, are not.
In general, writing down interruptions is a good idea regardless of
which category you’re in. If you do get back to it on your own, it’s the
equivalent of a collection point dual entry; it’s just that you also used
the point between your ears. When you see the task again in a
recorded inbox, just mark it done.
However, there’s another good practice here. Sometimes it’s not
possible to stop everything and write something down. Basic memo-
rization skills are useful, and the downside of rapid collection is the
same as when you got your first calculator, and all your long division
abilities went out the window.
When you’re collecting new things, and the main thing you’re doing
isn’t demanding (such as traveling between appointments), see if you
can keep it in your head as well. It’s a skill that improves with use,
and you’ll need it other times. When you’ve also stored them outside
your head, all the pressure is off if you forget a few.

Do Things

After all this setup and work, doing the tasks in your system is the
easiest part, as you’ve front-loaded all the necessary thinking and
planning. I discussed how to do this back in The Process of Using Your
Tools, but now is the time to move from theory to action:

1. Review your calendar to know upcoming events and judge how

much time you’ll have for your task lists. Go to your hard events,
skip soft events as needed, try to honor your time blocks.

2. Start with the list you choose to be first, based on either routine or
the needs of that day. Night owls may want a low-energy warmup to
start their day; morning people may start with a particular project
they want to focus on, or go straight to the next step and start their
Due list. Or you could go the traditional route and have a list includ-
ing checking email, returning calls, and chatting with coworkers.

3. Work on your Due list. Either complete it before moving on, or do a
batch here and go to the next step.

4. Work on your Flagged list. If you didn’t finish your Due list, return
there after a while, then repeat steps 3 and 4 until both are done.
It’s more important to complete your Due list.

5. If you finish both and still have time, you can go to your other lists.
Go to a particular project and concentrate on its next tasks, select
new tasks to flag across multiple projects and lists, work on upcom-
ing due tasks in your “look ahead,” or just enjoy an easier day.

6. At the end of the day, check tomorrow’s calendar and Due list to get
an idea of what’s ahead. If you need to cancel soft events, move time
blocks, or unflag tasks to make your lists more manageable, doing it
now will save you decision time later.

7. Repeat daily until the end of your review period, when you review
your system to document what you’ve done, improve how it works,
and select your next tasks. I explain how in Track, Review, Adjust.

Manage as You Go

As you work through your calendar and your lists, there are several
habits you should get into to keep things up to date (and lower the
amount of review upkeep you’ll be doing later):

• When you check off a task, create a task for any needed followup.
For example, you’ve sent an email, and you need a Waiting For to
track whether you’ve gotten a reply. Some email apps can make this
a one-click step, creating Waiting Fors when you send messages.
This requires a pointer in your task app—not to the individual
message, but a recurring one to check all your email Waiting Fors to
clean out what you’re not waiting for any longer, and to review what
you still are. You only need to set up this pointer once. After that,
this Waiting For collection point is perfectly reliable, as you’ll be
sent to check it on any schedule you choose—which you should
modify to more or less often as necessary or convenient.

Note: I use MailSuite with Apple Mail for Mac to show me all of my
Waiting Fors automatically; you can do the same thing with Gmail
labels, or with any email provider and email app by dragging particu-
lar sent messages from your Sent folder to a Waiting For folder.
Other apps and providers may give you more options.

If you do create a separate Waiting For task, it should be entered

into the same project in your task app, since it’s after the task you
completed, but will stall the next one if the project is sequential. If
your Waiting For is elsewhere (as in the above example), you can
add a pointer in the project that stalls the project (like any unfin-
ished task would); check it done when you’re no longer waiting.

Note: It’s fine to have one pointer to the place that stores many
things like Waiting Fors, and a second one pointing to a particular
item in it. It just means you’ll have two opportunities to be reminded
of your most important items, as only those get individual treatment.

• When you skip an appointment, you can’t make it up later, but you
might need a new task, such as getting a copy of the minutes of a
meeting. However, if you skip a time block, you have to drag that
event to somewhere else on your calendar. It corresponds to a
future hard due date, so the time has to be made up elsewhere.

• When you change or blow past a due date, make a note of it in the
task. I add a capital “D” at the end of the task name. You’ll use this
as a reference when you review later.

Other things to note for later review:

‣ Whether you’re working entirely off of your Due list, to the

exclusion of your flagged tasks.

‣ How many time blocks you honored at the time you set them,
how many you completed at a different time, and how many you
missed entirely.

‣ A general sense of whether your estimates of how much you

could accomplish during a review period, back when you made

them, had any basis in reality compared to what you’re actually
getting done.

The Sane Way to Deal with an Insane Past Due List

Some days, there’s more on your Due list than you can finish. You’ll
get an immediate sense whether today’s one of those days when you
see your list, and you might update that opinion when you reach that
“20-minute task” that takes two hours.
Make this less frequent by spot-checking your upcoming Due list in
the morning, or the evening before. Once you’re working on your
lists, you may only see a contextual subset of your due tasks. Taking
it all in at once, while daunting, also gives you a chance to prepare.
So here you are, with a Past Due list piled up from previous days, on
a day that already has its own Due list. You can’t just “do what’s
urgent,” because it was all urgent. How you deal:
✦ Scan your Past Due list for only the “Illudium Q-36” items, which
as everyone knows, cause an Earth-shattering kaboom. It’s not
enough to be merely consequential; look for what’s truly awful and
will not mellow with age. Pick them out, but don’t start them yet.
✦ Turn to today’s Due list. Everything here is not a crisis yet, but
may become one if you do your Past Due list first. Compare the
importance of not letting that happen, with your handpicked
ubercrisis list, and do them in the best order you can determine.
✦ Ignore the rest of today’s due tasks until you’ve completed both. If
some of those are still unfinished at the end of the day, add what’s
left to your backlog and repeat the entire process tomorrow—when
you should be even more selective about what’s a top crisis.
✦ When you’re current and get to your Past Due list, don’t immedi-
ately do those things. Once a deadline is missed, sometimes the
task just isn’t urgent anymore. It may have a natural new due
date that’s not immediate, or it may even be a Whenever task
now. Assign them the new due dates they deserve. Then only
work on what’s actually still due.
✦ Usually, you should tackle the remaining list in reverse order. The
deadline you missed yesterday is likely to be more salvageable
than the one from two weeks ago, which can go to 15 days with-
out being that much more late, relatively speaking.

Process Your Collection Points

This isn’t a final step; it’s a recurring task you’re continually attending
to. You’re regularly capturing new information and tasks in your
collection points. Some of these will have their due dates and flags
immediately assigned, and if they pop up on a list, you mark them
done before you organize them. Everything else has to be reviewed,
and reviewed often enough that you trust capturing in the first place.

The first thing you do: ruthlessly cull. When you were getting things off
your mind as quickly as possible, you disengaged the filter evaluating
the quality of your ideas. Now it’s turned on. Go ahead and delete
anything that’s unimportant, or possibly expired since you recorded it.

Tasks that were new ideas for a project get organized into a project
structure, or are the seeds of new ones. Other tasks are single items
that are candidates to be future flagged tasks; I simply move them to a
list called One-Offs for future review—flagging them on the way if
they’re still a great idea to do soon. If you prefer, you could have
multiple such lists, dividing these up any way you choose.

You may find that you’ve recorded things multiple times, either several
times in various collection points, or by collecting items that were
already in the project. Don’t worry about this; it’s part and parcel of
getting things off your mind quickly. Give the duplicate a glance to
make sure it doesn’t contain any unique details not recorded else-
where, then delete it.

Now you lather, rinse, and repeat the above until you retire to Aruba,
or to wherever Arubans retire to. But you’ll get better at it as you go,
starting with the best practices in the next chapter.

Special Handling for Email
Email is a special case. It says “inbox” right there on the tin, the
same word some apps use for collection points, but it’s not one.
Certainly many emails lead to tasks, but an email is only useful as a
reminder when its task is implicit. And since your email inbox grows
on its own, at a pace you can’t control, any implicit tasks will be
mixed in with messages you need to think about before you do
anything, and tons of other messages requiring no action at all
cluttering up the space.
As a consultant, I’ve seen how hundreds of people organize their
mail, and I think a lot of time here is wasted. My suggestions:
✦ I use Gmail labels—which combine the features of email folders
and tags—to assign messages to groups. I change these frequent-
ly, but right now they are: Urgent, High, Whenever, ReplyTo,
Waiting, and Reference. Each label gets its own recurring task,
and the more important ones recur more frequently.
✦ The Waiting and Reference tasks are to clean them out. Each of
these mailboxes contains only actively useful information.
✦ ReplyTo is a separate label because I frequently want to change its
priority in relation to High and Whenever.
✦ If you have “moderately urgent” messages, use “Before
Tomorrow.” High takes precedence most of the day; at the end,
this does.
✦ Once it’s labeled, I archive the message out of the inbox. Until I’m
working with that label, I don’t want to see it again.
✦ Anything that needs more organization than the above, I bounce
into my task app.
✦ And for the days I don’t get to email at all: a separate recurring
task to skim all new subjects and senders, triage them as Urgent
or whatever, and mark the rest as read (although I haven’t) and
leave them in the inbox. That way, I know that what I skimmed
can wait, I know unread messages are all genuinely new, and that
messages remaining in my inbox are unread and waiting.
I wrote a story for TidBITS about my email strategy, and specifically
why you shouldn’t use email snooze features when better methods
are available.

Implement Best Practices
Everything preceding has been recommendations for things you
should do to set up your system. This chapter is a collection of things
you can do to make it work better for you. It’s neither exhaustive nor
mandatory, but chances are, you’ll find ideas here that will save you
quite a bit of trouble.

Some of these practices are a feedback loop, also known as virtuous or

vicious cycles. We’re shooting for the virtuous ones. They’re when
something positive is crystallized into a method of informing the future
ways you do it, and something negative is noted to be avoided. The
more often you go to the gym, the more you’ll enjoy going to the gym.
(Or so I hear.) At first, nearly everything you plan during a review
period is no better than an informed guess about what performing a
task will be like; a feedback loop captures information by drawing your
attention to your habits and outcomes, and (mostly) painlessly im-
proves doing it the next time.

Web content: There’s an additional list of technology tips and tricks

on the book’s blog that are either specific to particular work styles or
platforms, or that needed more space to describe than we have here.

Planning Techniques

These are approaches that you use when you plan out a review period.
They don’t specifically affect your planning style. Instead, they’re
methods of making sure you stick to your plans, by making your work
more pleasant and manageable.

Use Sprints
Many tasks that aren’t particularly onerous come with a great deal of
friction because they’re so darned long. It’s one thing to have a recur-
ring task to wipe down and mop the kitchen; quite another to spend an

entire weekend cleaning up the house and throwing out 1,000 things in
the basement and garage.

A sprint is any task that you tackle for a set period of time, regardless
of whether it’s anywhere near done at the end of it. Use them when any
of these happen:

• You find yourself neglecting or procrastinating a task because it’s

such a huge chunk of your day (or your week).

• You have a task that you don’t mind doing, but it’s large enough to
eat time that you need for other things. You don’t want to get in-
volved with it, then look up when the sun is setting. A long time
block makes it tempting to keep on going; a sprint gets you in and
out quickly.

• Finally, use a sprint when you want to limit yourself on pleasant

things, by noting how long you’re allowed to do something you
enjoy before you move on to something else. My A.M. reminder to
check news and Facebook comes with a 30-minute limit, and from
experience ignoring it, I’ve added a timer.

Note: Self-limiting sprints are required to corral dysfunctional behav-

ior that impedes what you’ve agreed to do. A mid-day Facebook
break can help keep you going; if it extends from lunch until 3 P.M.,
you must use a limiting sprint.

Set a sprint up as a recurring task, and delete it when it’s completed.

Make it repeat often enough so that the task doesn’t get bigger in your
absence. For example, I said earlier that my daily email regimen is
“new messages + 24 hours of backlog.” You could also say, “spend 30–
60 minutes on email,” but only if that is enough time that the mailbox
doesn’t get larger than when you started by the next time you get to it.

The recurrence and the amount of time you dedicate to the sprint is the
feedback loop. Adjust both until you’re making sufficient headway, or
to maximize your willingness, and perhaps enjoyment, when you get to
the task.

Have Triggers
A trigger is a specialized form of paying attention. It’s an action, an
outcome, or an environmental circumstance that you want to note,
because you can then respond to it differently. Humans have tons of
triggers that kick off habitual behaviors; it’s one of the strategies we
use to run 90% of our lives on autopilot. Feel distractingly hungry,
have a snack. Go to the bathroom when you need to. Itch, scratch.

For our purposes, we care about two kinds of triggers:

• Those that lead to dysfunctional behavior, or a dysfunctional out-


• Those that serve as an indication that dysfunction is already under-

way, and should be addressed.

For example, people with attention deficit disorder, when we’re under
proper care, are trained to recognize the signs that we’re in a state of
monkey brain. At which point, we’re supposed to use a focusing tech-
nique (or a stimulant like caffeine) to calm it down. We learn to pay
attention to things that normally go unnoticed. We don’t do this by
seeing the things themselves (some of which are literally impossible for
us to see, like a blind spot), we do this by having triggers that let us
know they need attention.

You may not need it for the same reasons we do, but we have had the
benefit of being taught how to do it, and the technique is generally
useful. A few things that may act as your triggers:

• You’re normally a morning or evening person, but you’re not in the

right gear during those times.

• Something that normally doesn’t bother you sticks in your craw. Or

you’re more short-tempered than usual.

• The stack of mail on the credenza is taller than your child.

The key thing is to identify which are your canaries in the coal mine. A
stack of unopened mail, for most people, indicates that they’ve simply
neglected that task. But maybe it tells you something entirely different:

that small thing says you’re neglecting your home management, which
in turn means your work-life balance is entirely out of whack.

The steps to effectively use triggers are:

1. Learn what they are. You don’t choose your triggers, you already
have them. You just haven’t noticed. Learn a trigger by correlating
an event, environmental state, or behavior with the larger problem
it indicates, or a problem that it causes that’s not proportionate.

2. Pick a strategy to address the situation you’ve now noticed. It

doesn’t have to be a good one, it only has to be different. “When X
happens, I’m going to change Y to see if that makes X go away.” It’s
not about getting it right, it’s about changing the habit. If it doesn’t
work, at least you’ve broken some old routines that might have
contributed to the problem; it will be easier to switch in different
activities when you try the next one.

3. Incorporate that strategy in your next review. That is, you have an
overall idea of what you want to change, but you won’t change it
until it’s expressed at the task level. “I’m stressed because I’m
working too hard” becomes “I’m going to flag fewer (or no) When-
ever tasks for a week.” Merely saying “I promise to do better” is not
going to cut it.

4. Make a task, set it to due just before your next review: “Did X
happen again?” Incorporate that into your next plan.

5. Repeat the above until the problem is solved, or ameliorated. This is

a feedback loop; with each repetition, you refine your strategy for
improved outcomes. In the latter case, sometimes you’ll decide that
the problem is simply part of your character; you either can’t or
won’t change those spots. That’s fine, as it’s a realistic appraisal.
That doesn’t mean you can establish repeated Band-Aid patterns
that lower the consequences.

6. Watch for the recurrence of the trigger. If it happens again, go back

to step one. If it doesn’t happen, you won’t notice, so the task is
there to remind you of its absence. It’s time to celebrate; most
people can’t fix themselves the way you just did.

Sometimes, a trigger will indicate that you’ve gone entirely off the rails
in a big way. That’s when you try to Fail Successfully. It’s perfectly
common, and don’t let it throw you. That’s why we have that chapter.

Flag Fewer Whenever Tasks

If you’ve followed earlier directions about how new projects and tasks
land in your task app, you’ll have a large number of items that don’t
have due dates, and they’ll be on one or more huge lists. During every
review, you’ll note how many of these you completed, and go through
the rest of them to see what bubbles to the surface. The feedback loop
here is to have your Flagged list approach a manageable size over
time—which usually means either “can be completed in my available
time” or “always has a little extra on it so I don’t have to think about
what to do next, until the next review for new things to flag.”

Most of your Whenever tasks will be good ideas and attractive short-
term goals. (If you’ve been ruthless enough, your middling ideas were
self-censored between your collection points and your task app, and
never got here.) Since they don’t have time pressures, you’re less likely
to be rigorous about accurately estimating how much time each one
will take. It’s very easy to overeat during the flagging process, and put
more on your agenda than you can handle.

There are two ways to fix or ameliorate this:

• Really understand that flagged items you didn’t finish aren’t “falling
short,” they’re just a notation of how much you tried to do. If you
don’t finish your list, you’re not behind, you’re just working sustain-
ably. It’s not a bad thing to pick out too many things if you have this
mindset; you’re merely front-loading several review periods at once.
You only need to cull some flags so they don’t mask other flagged
items that are more important.

Note: The exception: when you know that you slacked off last week.
But you can’t say you did based solely on comparing it to the size of
your list. You must compare to your average prior output, as that’s
the only realistic indicator of what you can accomplish.

• Be more selective when flagging. If you run out of flagged things to
do, you can always reward yourself with an easier week, or go back
and pick out more. I’m not sure why people feel the need to over-
schedule themselves; when faced with unexpected free time, most
people fill it with useful things. You already have many of those
waiting for you on your unflagged list.

Track Your Due List

Even after removing soft due dates from your Due list, some workflows
can keep them lengthy. This is a problem, because you tackle your due
tasks before you get to your Flagged list; when you consistently have
enough due tasks to fill your days, you’ll never get to your Flagged
tasks, some of which might be important.

It’s tempting to solve this problem with soft due dates for your flagged
tasks, and I hope it’s clear why you shouldn’t do that. You can try to cut
down on your due tasks—especially recurring ones, as they continually
contribute to the problem—but another technique is to create a
pointer: “Work on your Flagged list.” Set this pointer to recur and
assign it a firm due date, so it shows up on your Due list.

When you get to this, it effectively (and temporarily) promotes your

Flagged list to the priority of your Due list. You’ll switch from Due to
Flagged, work there for a while (probably determined by how many
due tasks are waiting for you), and switch back to Due when you’re out
of time, or when you’ve completed a satisfactory number of flagged
tasks. Tracking your Due list to note whether you need a pointer to
your Flagged list is a feedback loop, because you can vary how often
the pointer repeats until you think your Flagged list is getting sufficient

Note: For tips on how to reduce the pain of recurring due tasks, see
Force Your Recurring Tasks to Be Humane.

Use “Look Ahead” Carefully
Most task apps have an option to “look ahead” for upcoming due
tasks in the next few days, and put them on your Due list.
Remember: if a task is due tomorrow, that means it’s not due today.
It’s fine to want to “get ahead” by working on tomorrow’s due tasks,
but note that every time you do, you’re borrowing time from your
Flagged list. Future due tasks would normally not take priority over
your Flagged list, but this technique effectively does that. Generally,
don’t work ahead unless your Flagged list is finished, and you don’t
want to pick out new tasks to flag until your next review period.

Time Estimation Techniques

The problem with managing your time is that it ironically takes a lot of
time. You should try these techniques for a while, and discard them
with a vengeance if they don’t benefit you, as they’re higher cost than

Use Reverse Calendars

A normal project timeline is “do some work each week until it’s done.”
The amount of work is what you set; the day it’s done is the variable
that depends upon your output. This doesn’t work for large projects on
a long-term deadline. When “some work each week” turns out to not be
enough, you risk a steep rise in workload towards the end—and de-
pending on the size of the project, it simply may not be possible to

A reverse calendar is a good way to approach this problem. This sets

the deadline, and your time between now and that date is what’s
variable depending on what you need to do. It’s partially brainstorming
and partially time estimation, but the key thing is that you work
backward from the deadline date. Here’s how to do one:

1. Start with the project and the deadline date. Just know what they
are; don’t put them anywhere just yet.

2. Brainstorm the list of tasks or subprojects that are necessary to
finish the project. You can do this in your task app, or any better
tool you prefer. When any of these have obvious subtasks, break
them down as thoroughly as you can. The last task on the list is the
one that when it’s completed, so is the project. Set its due date to
the same as the project.

3. Make a best guess how long the last task will take you, and count
backwards that many days. This is the due date for the next-to-last

4. Repeat with every subproject and task until you reach the begin-
ning. You now have a first task with a due date. Estimate the
amount of time it will take, and you have a start date for the entire
project. But it’s completely unrelated to one very salient point:
today’s date.

a. If the date is in the future, rejoice. Just start it then. (Or sooner,
but note: that’s optional. Don’t let “getting ahead” steal time
from more immediate priorities.)

b. If the date is in the past—well, that’s a problem. You have two

choices: tighten up the estimates for how long each step will take
(which implies you’ll be putting in more time to get it done), or
renegotiate the deadline to have more time.

5. Put these tasks and due dates into your task app, or enter them as
time blocks on your calendar. These time blocks ad due dates are all
firm, but in most projects, early on they’re on the softer side as you
have latitude to reschedule your work. The closer to the project
deadline you get, the harder they become.

Note: “Reverse calendar” does not necessarily mean “a different

calendar or color”—it can be a different calendar, but it can be

merged with any time-block calendar you already have. (I don’t like

that “reverse calendar” may be confusing this way, but I’m calling it

that as it’s the common term for this sort of backward scheduling.)

6. When you start the project, track your progress against your due
dates for each task. The rest of the project expands or contracts like
an accordion as you proceed: when you finish a task early, you can
adjust the future due dates to give some tasks more time. When a
task runs overtime, you have to adjust your due dates with less time
between them.

Some people save reverse calendaring for big projects, while others are
highly effective using it for nearly everything. Try it, and keep using it
if it works. It’s an excellent technique for targeting a habit of procrasti-
nation—if that’s an issue for you, give it a try with something small.

Set Estimated Times and Track Them

Some productivity software has a place to put in a time estimate when
you create or review your tasks. Even when it doesn’t, you can always
add it in the notes field or the name of the task itself: “Take out the
trash (15 minutes).”

Estimating your time can be a very useful tool, but it’s also a good way
to get lost in the weeds. There’s no point in doing so if it doesn’t pro-
duce actionable data back to you. Meanwhile, both estimating and
tracking your time are fiddly processes that can eat into project time—
especially for those of you who like to play with new software, as there
are 100 ways of doing it and you’ll want to try them all.

I don’t track my time on most tasks, but I absolutely do so when there’s

something I need to get a handle on: I find that it’s taking up too much
time and I need to rein it in; I think I can accomplish it in a slice of
time between other tasks, and I’m laughably wrong; or I have some
professional reason to do so. Here’s the process I use, which keeps
fiddling to a minimum:

1. When I create a task, I assign it an estimated time. Let’s say it’s 30


2. When I complete the task, I note how long it took me. (Roughly. I
have several different ways of setting timers and stopwatches, but

nearly always, this level of precision is not needed.) We can call that
40 minutes.

3. With recurring tasks, in their note field, I write the following: “(30 +
40) / 2”. If you’re keeping score at home, that’s my initial estimate,
the clocked time, and a divisor that counts the values to produce an
average. Right now, it’s easy to see it’s 35 minutes, so I put that into
the estimated time for the recurrence of the task.

4. Next time I complete it, I update the field: “(30 + 40 + 60) / 3”.
Now you’ll see why I type it like this: I copy that and paste it into a
Google search bar or Spotlight, and instantly get the result. No
thinking required. Again, I update the task.

5. After five or ten repeats, the divisor is large enough that a repetition
doesn’t change it much. Go ahead and set the task with the last
estimate, and stop modifying it. Come back and do this again,
though, if something changes and the task starts taking much more
or much less time than you’ve predicted.

Voilà. Now you’re making your estimates with science, and using a
feedback loop to create better estimates for all future tasks, as you’ll
get a feeling for your tendencies to underestimate or overestimate
(usually under), and can adjust accordingly. (I typically make my best
guess, add 50%, and enter that number.)

How to Track Your Time

Ask any lawyer or consultant who bills by the hour, and they’ll tell you
that tracking their time down to the billable minute is exceedingly
annoying. It’s like working for a boss who requires receipts for every-
thing, and you spend your entire day spending money.

That said, if you’ve ever looked a clock reading 4 P.M. and asked,
“where did the day go?”, this is the best way to find out. As with esti-
mating time, you only need precision if you’re getting paid for it. Two
methods to try:

• Open a document or outliner, enter the current date and time, and
write a narrative note of what you’re doing, or what you’ve done

since the last time you jotted it down. This is for your personal use,
so it can be a few words only you can understand, or Nobel-winning
prose. Whichever makes you happier. When you create a new note,
you can add it at the end, or go to the top of the document and
insert it, in order to make it chronological or reverse-chronological.
Likewise, you can make a new document every day, every review
period, or always use the same one. Use any tool you like, but it’s
better if you use one with a shared document on all your devices.

• You use your calendar to schedule your future. Why not also sched-
ule your past? Logging what you’ve done for the last hour is 30
seconds of clicking, dragging, and typing. I keep a different calendar
(with its own color-coding) for this, and I also track which events I
attended by moving Appointments and FYIs into a Canceled calen-
dar if they’re blown off. Every review period, I can look over the past
week and get a sense of whether I need to get out of the house more.
(Usually yes.)

You can also do this in your task app, as nearly all organizational apps
allow you to attach whatever notes you want to any task. The problem
is that when you mark it done, the whole point is that it gets whisked
away. Eventually, most software archives it or deletes it entirely, so
your database doesn’t get huge. I use OmniFocus notes for future
tasks, but I prefer my running narratives to be separate, searchable,
and easily found.

Switch Up Tasks and Time Blocks

If you have a task or project that didn’t get enough time, consider
making a time block for it. This bumps up its effective priority, because
any task without a time block has to flow around it.

Likewise, if a time block isn’t working for a particular task, stop putting
it in your calendar. If you like, put these tasks in a new unordered
project called “Former Time Blocks,” flag them all, and set a daily due
task to point you to it. Assign firm due dates to the tasks that need
them. This could be a feedback loop—if you spot a pattern for what

works well as a time block and what doesn’t, you can use that informa-
tion for future decisions about similar tasks.

Use Prioritizing Contexts

Contexts can give tasks rough priority sets. Don’t attempt to use
priorities to create perfectly ordered lists; that’s way too much fiddling
time in your task app. Instead, create conceptual contexts that allow
you to focus on what’s most important first, then move on to the next

For example, I’m self-employed; there’s very little I do with my day

that I can’t somehow designate as “work.” Just about every webpage I
read, or any software app I download, can qualify if I’m not careful. So
my work tasks are given the following contexts:

• Revenue: Only the things I get paid for. Easy to identify, but
without the context, they can be the last things I do.

• Prep: Tasks that are necessary prerequisites for revenue, or at

least, a highly likely prospect of revenue. Following up on a solid
sales lead is prep; going to a networking event to schmooze is not.

• Non-revenue: All the myriad work things I have to do that don’t

qualify as the first two. Learning new software and programming
techniques, marketing, revising my website, and reviewing my
system: all work, all non-revenue.

Everything else on my lists, I call “Discretionary.” There’s some gray

area there, because there’s “fun work” that overlaps with non-revenue,
and I don’t much bother to note the difference. The key thing is that I
(theoretically) don’t switch to discretionary tasks before I’ve knocked
off a solid work block, and I don’t confuse other things with the work I
need to do to get paid.

Note: However, note the decisions you made when you started.

You’re allowed to decide that what I call “discretionary” is as impor-

tant, or more so, than work. Your life, your rules.

Satisfaction Techniques

These tips involve what to do about long lists of undone tasks. I call
these “satisfaction” techniques because sometimes they don’t indicate
an issue with a particular project. They only mean that you’re manag-
ing your system to maximize your own misery. No one feels satisfied
when they end a day with twenty tasks left over; everyone feels great
when they knock off a to do list before lunchtime.

These techniques don’t necessarily make you more productive, except

insofar that if you feel less stressed, you might get more done. They
primarily serve to incline you toward realistic planning. Err on the side
of being humane to yourself when you plan, and you’re more likely to
be happier with your work and your output—without lessening that
output, because you will use that “extra time” on other things.

Fewer Big Promises, More Little Ones

Consistent lists of undone tasks mean you’re biting off more than you
can chew, especially with recurring things that are never “done.”
Change these from big promises to the smallest possible task that still
reflects your goal. “Go to the gym three times a week” becomes “take
the stairs more.” “Clean the house” becomes “tidy up a room or two.”

You’re not saying you’re never going to do the big promises, you’re
only saying you’ll get there reasonably. When you’re reliably meeting
your small promises, you’re allowed to make them bigger, a little at a
time. Eventually, some become big promises.

Change Deadlines to Match Priority

Frequently, we choose priorities that aren’t reflected in what we
actually do. Most of the attempted fixes for this problem are some
version of “this time I really mean it” and “I’m going to double my

That doesn’t work. If something “should” be important and isn’t

getting done, then either it’s not important, or other things have to

take lower precedence to make room for it. No other choices here.
What you can do is watch what you’re accomplishing, because some-
times you’re going to express a task’s actual importance to you by
whether you’re doing it. (Yes, this can be a feedback loop. If you find
yourself doing this frequently, it can cue you to set future priorities
more accurately.)

This also applies to deadlines. Sometimes you have to renegotiate

them. If a project can’t be done on time, it’s better to plan for that, than
to blow the deadline in crisis mode. Find ways to extend the deadline,
or find an easier breakpoint at which you can call a project “done” and
add a later follow-up project that includes the tasks you originally
included as part of it.

Give Yourself Credit for Reading This Book

Right now, you’re reading this book, and ignoring everything else. If
you’re following the instructions, it’s probably taking hours. Congratu-
lations, you’re being productive right now.

Time spent managing your system is productive time. It may not feel
that way, because the only things it checks off your lists are the re-
minders to plan and review. But it’s productive, in the same way that
getting a good night’s sleep is productive: it’s necessary preparation.

Your periodic reviews will take up some time every review period. The
more you do it, the quicker it will be; you’ll know your tools better, and
you’ll pick up idiosyncratic techniques that only work for you, which
you can use to shave time. But not to zero.

At the end of a day partially spent on review, if you ask yourself where
the time went, one of the things you tell yourself is, “I invested time in
taking control, being less stressed, and doing what’s truly important to
me.” The mechanisms may feel like wasted time, especially if you spent
an hour learning a new app you might try, or laboriously transcribing a
stack of paper into your software. The purpose of why you did that is
absolutely not.

Be satisfied. It’s time well spent.

Don’t Forget: Peak Sustainable
One of the initial conceptual rules bears repeating here: Define 100%
as Peak Sustainable. Don’t blindly maximize productivity if your goal is
something else. If you accomplish that goal with maximized productiv-
ity, fine. Otherwise, you’re at “maximum” when you hit the limit where
further increased productivity makes you less satisfied. Pushing past
your physical limits or taxing your stamina will frequently do so.

Manage Your “Yak Shaving”

This technique is broken out because it’s entirely novel, and it doesn’t
fit in any of the above categories.

Yak shaving is a concept I first heard about from Merlin Mann on one
of his podcasts, although he didn’t coin the term. It refers to the fact
that a yak has many layers of thick, matted hair. Try to shave a yak,
and all you get is more hair.

Yak shaving is when you attempt to do something, and only then

discover it has a prerequisite. It’s quick, so you start doing that—but
then that has another prerequisite, and so on. Before you know it, it’s
six hours later and you’re looking up the average annual rainfall in

Note: Prime yak habitat, where they get around 17 inches.

Yak shaving also occurs whenever an intrusive interruption derails you

from what you’re already doing, because it seems short enough that
you don’t think twice about doing it. When something obviously will
take an hour, you decide whether to switch. When it’s “quick,” you just
do it. Then you discover its prerequisites, and so on.

Manage this by documenting your breadcrumb trail. I call this a yak

list. If you’re already creating a narrative such as what’s suggested in
How to Track Your Time, you can do it there. I find it’s more useful to
create a yak list per project, as the things on it are usually—but not
always—related to where I started.
A yak list is a reverse to do list. It’s not what you intend to do, it’s what
you’re already doing at the moment you record it. Start a yak list
whenever you realize that what you’re doing is not what you initially
intended to do. The hardest part is getting in the habit of noticing, and
I’ve found that having an open window titled “Yak List,” and another
one in Google Keep for when I’m mobile, primes me for the mindset.
The more often you use one, the sooner it will occur to you the next
time you do.

This is a time where a picture is worth a thousand words, so I’ll show

you a yak list in progress, from a real-life example when I was revising
my website on deadline. I’ll intersperse those with the steps to keeping
your list, as follows:

1. If you switched to another planned task in your system, and it’s

from the same list as your original task, that’s not yak shaving.
That’s prioritizing on the fly. “From the same list” means you didn’t
switch from due to flagged, or one context filter to another.

2. If what you’re working on is from another list, a new or spontaneous

task, or something you had to do to get to what you wanted to do,
it’s yak shaving. Start a list.

3. Add the intended task first, and make it bold or red or a big font. It’s
the keystone for the rest of the list.

4. Put your insertion point in front of that task, and add what you’re
currently doing above it. Then reconstruct the steps that took you
from what you intended, to where you are (Figure 16).

Figure 16: The beginning of a yak list, with the “official” task in
bold, preceded by the steps I took away from it.

Discovering I needed more features was an unknown prerequisite to

actually doing what I needed. When I learned I didn’t have them, I
had a prerequisite for that. Then the light dawned, and I started this
list. Having only two steps here is catching the yak early; in some
cases, you might be a dozen steps away from where you started,
especially if some of those were interruptions having little to do
with anything else.

5. Review those steps, and quickly determine if those things are gen-
uinely prerequisites for what you intended to do, or are at least
deserving distractions. Anything that’s not, you can store in a
collection point and drop. (Sometimes I put the entire yak list
document in a collection point after I’ve finished its important
tasks; anything unchecked is a collected idea.)

6. What remains are things you need to do before you reach your
original task. Some of these will spawn their own lists. This is why I
use an outliner for this: it’s easiest to indent the new list as part of
the main one (Figure 17).

Figure 17: A yak list that spawned a baby yak, with indicators

where the next things go.

As you can see, I added the baby yak by copying that task into the
middle of a new indented list underneath it, making the copied text
bold, then adding its own prerequisites and followups. The red text
shows where additional things go as you move forward. It’s entirely
likely you’ll be inserting new things up and down the hierarchy,
because working on one bit may give you an idea for something else.

If you suddenly realized “hey, this is a baby yak,” and had to retrace
your steps again, give those steps their own review to make sure
everything is genuinely pertinent. Add what’s not to a collection
point. As you develop the habit, you’ll be able to recognize the
difference in real time and won’t have to write it down after the fact.

7. Work from top to bottom after everything is documented properly.

You need to tackle those prerequisites, in that order, if you’re going
to get to your original task. Anywhere you have a baby yak, all of
those steps are in the sequential order you need to follow as well.
Note: Prerequisites are yak list items if they’re things you need to
do. Otherwise, they’re Waiting Fors, and they’re a stopping point.
Create a Waiting For in your task app that blocks your original task,
and have it point to the yak list, since it’s already decently organized.

8. Since you’re working from the yak list anyway, instead of collecting
items that are related to the original task, add them to the end as
followups. But if what you find yourself doing is an unrelated
distraction, make a note of it at the spot on the list you were when it
happened. Then also add it at the end, and indent and brainstorm
the tasks it created.

The note in the middle is so you can reconstruct the sequence of

events; that will be useful for refreshing your memory when you
refer back to this list. The brainstorm is at the end because it’s
unrelated to the original task, so you want it separated out in order
to disconnect it later.

9. If you finish your original task, review the list for what remains to
be done. If those items are nicely organized because of all the
thinking you applied while you were yak shaving, keep the docu-
ment and create a pointer back to it for any followups. You should
also keep any tasks here that are sequential with what’s organized.

Take the same pointer approach if you’re still working your way up
to the original task. All the organization you need is already here.
No need to move it anywhere else.

Other items, such as those brainstormed distractions, or related

tasks which might be done in parallel, should be moved. You don’t
want these things to accidentally become sequential after you finish
all the followups, and that might happen if you don’t see them again
until you reopen this list. The fastest ways to do this:

‣ Take a few minutes to slot those items directly into your projects,
skipping your collection points. You may have already started
organizing and brainstorming them during your yak shaving, so
you’re in the right place to organize them a bit further.

‣ Alternatively, duplicate the entire yak list document, delete
everything except these parallel and unrelated items, and toss the
whole thing into a collection point for later. (If you do, note that
your due date to get back to it is the earliest due date of anything
that lives here.)

Here’s how my yak list looked when I finished my website project. The
numbers in parentheses are purely for the purposes of this illustration;
they’re the order in which I added each line (Figure 18).

Figure 18: A completed yak list, indicating how hairy these things
can get.

As you can see, I’ve added checkboxes, and used them to help me track
where I was. You can also see where the yak list branched. Once I was
working several steps back from my original task, my yak list showed

me I was still hours away from getting anywhere near it. By item 12, I
was about ready to completely redo my entire site—which was mad-
ness. That led me to step 13, the ugly fix (which I called a kludge in the
list—in technical parlance, it’s something that gets the job done, but
you don’t want anyone to see how the sausage was made). I then
skipped every prerequisite the ugly fix allowed me to, and created
another baby yak for ugly fix tasks at step 14.

After that, finally, and eight hours into a one-hour task, I rearranged
my site for better presentation. Without the yak list, I might have spent
10 more hours trying to fix the things I skipped, having lost sight of
what I sat down to do. With the list, I knew exactly where I was
throughout. I had to stop and get back to this several times; the yak list
told me exactly where to pick up again, and why.

This is the level of granularity I personally find useful. You may have a
different one. Whatever works.

A few closing thoughts about yak shaving:

• The existence of a yak list is usually proof that you wildly underesti-
mated how long something would take. If your day is full or your
time is short, take a moment when you create one to decide whether
to plow ahead on your original task and delay other things, or to
work the same amount of time on it and come back to it later. A
little juggling up front may make the rest of the work less stressful.

• A yak list is a crutch for bringing mindfulness to your work without

effort. The habit of recognizing you need one becomes second
nature, but every time you do it, you’re paying attention in a way
you didn’t before. This happens again every time you add a new step
to the list. It gives you a chance to really consider whether what’s
there is a necessary task right now, or a worthwhile distraction. I
find this to be far easier when I’m keeping a yak list.

• If you’re on your second yak list of the day (on a new task, indepen-
dent of the first), maybe it’s just you. We’re all more distracted some
days. When you finish this one, consider setting a timer or notif-

ication to keep going off periodically the rest of the day, asking if it’s
time for your third.

Alternatively, if you find this to be a truly useful technique, start a

yak list every morning. When you’re not yak shaving, it’s narrative
documentation. Set the recurring timer, that asks if what you’re
doing is what you intended, as part of your normal workflow.
Eventually, you won’t need it—the habit will be set.

Track, Review, Adjust
There are two common metaphors for where you are while you work,
both oddly botanical: “in the weeds” dealing with your tasks, but
maybe “missing the forest for the trees.” Your regular review is your
chance to check in with your prior decisions, change them as appropri-
ate, and make your system into an accurate map of the territory.

The review is when you read through your lists in their planned struc-
ture. During the review period, you may have worked with collated lists
of their individual tasks, without seeing the overall structure much.
This is your time to approach it from the top down. Most of your
review time will be in your task app, but there are a few things you’ll do


These are the steps to take while reviewing your project structure. Your
task app may have a way of reviewing your projects sequentially, so the
fastest method is to view a project and apply any relevant instructions
below—only a few will be needed per project. This will come naturally
to you with experience—in the meantime, while you’re still referencing
this list, you may want to make one pass for each chunk of review
instructions you can hold in your head at once:

• Project status: Perhaps not updated during the week, so bring it

up to date if there’s anything you forgot to note.

‣ Mark completed projects as done. With most software, this

automatically marks all tasks it contains done as well, so don’t do
this if there are lingering followups, or at least, not without
moving those elsewhere.

‣ Cancel any projects that have been dropped. In most software,

this leaves the project in your database for reference, but makes
all its tasks inactive.

‣ Set a later start date for any projects now on hold. This also
should cascade to all its tasks. If a hold is indefinite, some soft-
ware has an “On Hold” status; otherwise, I set the start date to
January 1, 2030, on the theory that none of my real projects will
ever be deferred to that date. Therefore, it has special meaning
for me. You can use your kid’s 60th birthday.

‣ Review projects that were previously on hold, or had a deferred

start, to make sure none of them have become active.

• Documentation: If you’re using your task app to keep narratives

or other notes about your projects, make sure they’re complete with
recent tasks and information.

• Waiting Fors: These get special attention because they’re easy to

forget to record as they crop up. Add them for any task you can’t do
yet. Usually, you do this by creating a Waiting For task as a subtask
for what’s blocked; the parent task does not become available until
the Waiting For is marked done. If the task already appears in a
sequential list, you can alternatively put it in right before the
blocked task. Reminder: set the due date for when you want to be
reminded the Waiting For exists, not when the parent task is due.

• Parallel and sequential adjustments: When a sequential

project is accidentally set to parallel, you’ll see unavailable tasks on
your lists prematurely. When a parallel project is set to sequential,
tasks that are available are erroneously removed until you do the
first one. Setting the wrong one is easy in most task apps—and can
be quickly fixed with a checkbox or menu item—so make these
adjustments if you didn’t see what you were expecting on your lists.

• Reverse calendar adjustments: If any projects have had their

overall due dates changed, check to see if their tasks need a new set
of due dates to keep it on track. Do this for projects that are due
either sooner or later; when the overall deadline is delayed, if you
don’t also modify its reverse calendar, those old due dates are
actually ahead of where they need to be. That might crowd out
legitimately due tasks, or rob time from flagged Whenever tasks.

• Individual, and non-repeating, due tasks: You likely updated
most of your due dates when you revised your reverse calendaring,
but if there are any tasks with an independent due date, give them a
quick check. (Repeating tasks get a different approach, when you
Force Your Recurring Tasks to Be Humane in the next few pages.)

• Flagged tasks: These are your Whenever tasks that you wanted to
give more prominence to. You may have a better idea now if you
have too few (you needed to go hunting for more), or too many
(some moderately important things obscured the truly important—
or you felt bad that you didn’t get to them all). Adjust accordingly,
add flags to any tasks you want to promote—then, if you have to,
adjust again now that you’re seeing the whole of a longer list.

• Estimated times: If you’re tracking these, and you’ve kept notes

on actual time but haven’t yet updated the tasks, do so now.

Note: You may eventually have levels above your top-level projects,
where you determine if they are aligned with multi-year plans and life
goals. We haven’t addressed that yet, but we will when we Consider

Individual Tasks

When you emptied your collection points, you moved worthwhile

individual tasks to one or more lists (usually a list of unordered tasks,
unless you’ve chosen to organize them more). These lists are likely to
grow very long as you move more collected items to them. Some of
their tasks may be promoted to projects in their own right, or moved
into other projects. Any that remain take a different approach:

• Some of these tasks will already be flagged, from when you moved
them to your task app or put them in a collection point, or during a
prior review. Most won’t be. Remove the flags from tasks if they are
no longer important or interesting, and add them to the ones you
want to prioritize for the next review period.

• As I discussed in Flag Fewer Whenever Tasks, it’s never necessary
to finish a Flagged list, as none of its tasks are ever due. But you
may find that flagging many tasks is causing the same problem as a
Due list with soft due dates: genuinely important things are waiting
for the far less important (but still preferable). In extreme cases,
unflag the entire list and individually flag only your top priorities.

• Depending on how you divide up your lists, some may indicate that
something important is not getting enough of your attention. As a
frivolous example: I like movies. I have a list of dozens to eventually
watch. The length of this list doesn’t matter, but when it grows
substantially, it draws my attention to whether I watched one
during the last several review periods.

Force Your Recurring Tasks to Be Humane

By now, you’ve figured out that a large chunk of your time is eaten
up by recurring tasks that don’t pertain to a project. Some of these
are hard due; if I don’t take my trash out Monday night, my kitchen
is going to be unpleasant for a week. But most of these recur at
whatever interval I thought sounded good: “Go through messages to
my primary email address every two days. Do a 30-minute cleaning
sprint three times a week.”
Earlier, I told you to make a note on any tasks that were overdue
when you got to them; I use a capital D at the end of its name. When
I review, if it ends with D, I lengthen its interval. Late attention to my
primary email changes it from “every two days” to “every 50 hours,”
because I don’t want it to go too much longer. But I might add a full
day to a cleaning sprint. If I miss the email again, I’ll set it to 52
hours, and so on.
You’re not committing to doing these less often. What you’re doing is
making these tasks match reality—and when you add different
amounts of time to them according to their importance, to also match
your priorities. If you find you now aren’t getting to some tasks often
enough, go ahead and tighten them up. Every task you didn’t tighten
contributes a little room for them.
This is another feedback loop, and a crucial one. The longer you use

it, the more your task app will give you a manageable Due list.

Collection Points

As I’ve mentioned, some people clean out their collection points when
they review, but this makes the review process onerous and monolith-
ic—and most of your collection points need more frequent attention
anyway. Your review is simply an assessment of whether you’re ap-
proaching them in a way that builds trust:

• Are any of your collection points dauntingly full? If so, adjust the
timing of your sprints (or recurring tasks to clean it out entirely)

Note: It’s hard to get into the mindset, but with the proper use of

flagging and setting due dates when you collect ideas, there is very

little harm in having many things waiting in a collection point. At

worst, good ideas sit for longer.

• Did anything urgent land in a collection point without a way of

alerting you, never to be seen again? If so, adjust your pointers such
that you can safely store items in that place indefinitely, while still
being comfortable knowing that key items will surface.

• Did you have any times during the review period when you needed
to collect something for later, with no place to do it? Can you think
of a way to avoid that situation in the future?

• Alternatively, are there any collection points you don’t use, and no
longer think you ever will? Delete their pointers, or maybe give
them longer intervals, in case you occasionally forget and put
something there.

Software-Aided Review
Some software has built-in review tools. You can set review recur-
rences on a per-project basis, so for example, a Someday project
only gets reviewed every six months to see if it’s time. Since you’re
looking at large swathes of your projects less frequently, your overall
regular review time can drop dramatically.
I recommend you skip these features for your first few reviews. Until
you get a handle on the review process, and which areas need more
tweaking than others, you want to put everything in your head, a
little at a time, for a short while. It needs to live there a moment to
draw enough attention to review properly. Once you’re more comfort-
able, you trust your review process, and you’re certain that it’s a
waste of time to look at certain things every week, that’s when you
implement these features.
If your software doesn’t offer a per-project review interval, there’s

nothing stopping you from putting the projects you want to see less

often into a folder titled, “Don’t Open Until Xmas.”

Depending on how much you want to micromanage your projects in

advance, the review process can be lengthy, or something you dash off
in 10 minutes. Most commonly, it will ebb and flow based on whatever
else you have to do on the day you review—which, since most people
do this over the weekend, should include leisure time. If you run out of
time and still need to plan something more, treat that as a project. Give
it a time block early in the week, then go put your feet up.

That’s how you handle your own time and planning. Now for the other
7 billion people on the planet, some of whom you may run into from
time to time.

Manage People (Gently)
You may be embarking on a new organizational journey, but you
probably don’t live in a hermitage on a mountaintop. You have to
interact with other people, and rely on them to get your tasks complet-
ed. I can’t make blanket suggestions for how to deal with them—
everyone’s different—but there are methods for keeping it all straight
for yourself.

Make Liberal Use of Waiting Fors

Any time you’re waiting for something to happen that’s not under your
control, that’s a Waiting For. Up until now, you may not have used
them much, because it’s not that onerous to glance at a task and decide
in the moment that it’s not on deck.

When you’re waiting for other people, though, Waiting Fors are cru-
cial. Anything you delegate, for which you still have final responsibili-
ty, needs to be tracked. Likewise, you don’t want to switch to a task,
spend time getting ready to do it, then immediately discover that you
can’t. A Waiting For tells you immediately that the task can’t be done.
If there’s no immediate action you can take to speed it along, you don’t
consider it in the first place.

Some tips for how to implement Waiting Fors when it’s someone else’s
job to get it back to you:

• Reminder: create a Waiting For by giving the task that’s waiting a

subtask: “WF John to email me.” Add a due date when you need to
be reminded you’re waiting, and an optional note telling you when
the task it’s blocking is due. The subtask blocks the parent, so
instead of seeing it on your list as something to do, you see it as a
reminder you’re waiting. You can’t check it off until you’re not
waiting anymore.

Note: When you look at your project, you’ll see the Waiting For in
the context of what’s waiting for it. When you’re working from con-
text lists, you don’t see it at all. That’s why you check your Waiting
For context list occasionally.

• If you’re organizing something in one of your other apps, you may

need a Waiting For but have no way of creating one. Edit the task
with a prefix, like “WF John to email me—Prepare the report for
Friday.” Next time you review, put this into your task app where you
can track it better.

• In a busy project with many interactions, you could have quite a lot
of tasks that are Waiting For something. Add one every time. Your
project likely has multiple moving parts, and things that you’re
doing in parallel. The Waiting Fors are a heads-up display telling
you exactly where you can move forward, and where you can’t.

• You can also use Waiting Fors to track what you’re doing in the
moment. You need a one-line reply from John right now because
you don’t want to switch projects, but there are other related tasks
you can do in the meantime. You don’t want to forget you need that
very soon, though.

Set a Waiting For with a due date in 15 minutes, or 2 hours, or

whatever short period of time is appropriate, then move on to the
other task. (A labeled timer can also work. But a Waiting For is
easier if you have to do this several times simultaneously for differ-
ent people.) You can completely forget you’re waiting, because you’ll
be alerted in short order. You’re still on the same topic, so you
maintain flow. You’re also not distracted by the blockage elsewhere.

• When useful, group your Waiting Fors with contexts by people.

Instead of using your usual Waiting For context, you could use
“Waiting for: John.” In some task apps, this is a nested context with
“John” outlined below “Waiting For;” in others, you can apply one
tag for “Waiting For” and another for “John.” When you don’t have
either, it’s a separate context. This allows you to make tasks that
waiting for something unavailable and out of your way, and also to

create a list of everything you need from John that you don’t have to
manually compile.

It might also be useful to have two sets of people contexts. That is,
contexts are useful to group all the things that are with someone,
and all the things that have been passed along to them. These are
confusing when mixed, so split them if you need to.

Note: Software that allows for tagging, instead of fixed contexts, is

perfect for this. It’s already a pain when a task has an “at office”
context and a Waiting For. With tags, you can tag a task as “Office,”
“Waiting For,” and “John,” then reuse those tags in different combi-
nations for other purposes.

Set Expectations

We’ve gotten in the habit of letting our tools set our expectations. Back
in prehistory when internet email was new, it was so quick compared
what we used to use that an expectation arose: any given email would
arrive in minutes, and so you could expect a reply in the same time-
frame. These days, email is more often used for long-form messages
that might take a while to reply. But any number of instant messengers
and text messages still carry the weight of needing to be on 24/7 to

This is bonkers. Any incoming communication could be an interrup-

tion, a time commitment, and a derailing switch to something else. Let
other people get swamped by that; you’re going to manage them better.

This involves getting the people communicating with you to under-

stand the limits you’re setting—and suffice it to say, they might not go
along with it happily or immediately. But you can gently guide them in
the direction of working with you better:

• Make clear when you’re available, and when you’re not. Some
people have the freedom to say, “For these two hours, I’m available;
the rest of the day, you’re getting in line behind my work.” Most

have to do it the other way: “For these two hours, I’m heads-down
on a project or in a meeting. You’re going to wait then.”

• If there are VIPs who do get to go to the front of the line, no matter
what, set up an alternative method of reaching you and tell people
about it very judiciously. For example, Slack messages are “get to it
when I can,” but messages to a private Gmail address, that only a
few people have and no one can guess, hit your radar immediately.

• Use tools that automatically convey your availability, but not neces-
sarily why you’re unavailable. Most shared calendars have two
levels of sharing: the open share where people can see your events,
and the private share that only displays what times you’re busy. Use
private shares to mask your appointments, but by all means, use
open shares when you’re traveling for work or on vacation. That
alone should signal people to alter their expectations.

• When you aren’t available, tell people what actions to take in your
absence. I consulted with a colleague who needs to manage time
away from his desk, but who is the only person who can sign off on
dozens of approvals throughout the day. On his own, he had already
grouped several short meetings into one long recurring appoint-
ment. I suggested that he additionally tell everyone else, “on Tues-
days, those approvals have arrive by noon, or you’re going to wait
until Wednesday.”

• When an urgent communication (that is, their urgency, not yours)

arrives anyway—and they will, because people love crisis mode—do
the following:

‣ For short replies, send back an immediate email saying, “I’ll get
to this at [whatever time you’ve already set to handle things like
this].” Your devices and computers probably have text-replace-
ment tools, which let you type “wr4p,” and it types out that entire
sentence. After 4 P.M., send the “11 A.M. tomorrow” message

‣ If you really need to go undisturbed, use the vacation reply

feature that’s probably built into your email. It works when

you’re away for a week, and it can work when you’re away for 90
minutes. (Ideally, set a specific reply about when you’re available
again, and if you can, set the vacation message to auto-expire.
I’ve lost count of the number of voicemail boxes I’ve heard tell
me in June, that whom I’m calling is out until April 23rd.)

‣ For messages that need longer replies or substantial preparation,

flip to your calendar, make a time block for it, and immediately
send an email saying, “you’ll get a reply at [the end of that

A fair number of your correspondents will immediately write back,

saying that this is unacceptable. You’ll have to do a gut check re-
garding their relative importance (and position in relation to yours)
as to how you reply further. But you can “train” them over time. The
more you hit the deadlines you’ve promised them—you actually do
send your reply at 4 P.M.—the less likely they’ll object in the future.
Your reliability means that they can plan out their time, even if they
don’t get the instantaneous response they thought they needed.

Note: In extreme cases, you may want to buy them a copy of this
book, and send it to them with a note, “read this chapter on manag-
ing your Waiting Fors.” Joking. Well, not really.

Manage Sideways and Upward

If the person waiting for you is a subordinate, you may have latitude to
say, “Not now, come back when it’s convenient.” Less so when you’re
dealing with peers, bosses, and people like family members who are a
bit of both.

In the latter case, setting expectations is a matter of negotiation, and

the way to do that is to convince them to be reasonable. Here are some
ways to do that.

Note: Maybe. It depends on the other person. Your presentation
matters. Don’t use a formal technique to show your spouse why you
need to do the dishes less. Adapt to the occasion.

Document How Busy You Are

In cordial work relationships, or with a spouse (whom you’re hopefully
also cordial with), it might be enough to say, “I’m swamped this week.”
More demanding co-workers and bosses might not buy that on your

Note: The following steps take a while to complete, so instead of

waiting until you need them, you may want to do them in advance so
you have what you need in your back pocket. Side benefit: they also
show you how busy you are, which you may not be fully cognizant of.

One way to get them to be more reasonable, is to demonstrate to them

why they’re currently being unreasonable:

• If you don’t use estimated times for your tasks, start doing so. Make
them as accurate as possible (using the methods in How to Track
Your Time), because if you claim a 10-minute task will take you a
half hour, that weakens your argument.

• If you’re not using many time blocks already, try using more. You
may want to use two different calendars for time blocking, with
different colors: one for your routine work that happens every week,
and another for the specific projects filling up your time. It helps to
demonstrate that you’re busier than usual.

• Once you have good documentation, take it to the person you’re

renegotiating commitments with. They might still demand to be
given priority, but at least they now understand the cost of what
they’re asking for, in concrete terms.

Enlist Them as Collaborators
Let’s face it: nearly everyone, shown the above, will launch their ready-
made argument why they should be more important than everything
else you were already doing. There’s only one good way to handle this:

• List the new request alongside other tasks you have to do in which
they have an interest. You don’t want to tell Bob that you’re slaving
away for Carol, unless Carol’s outcomes are something Bob also
needs. Tell Bob what you’re doing for Bob, or for the people he cares

• Ask them, “Which priority should I lower in order to raise this one?”
When they say, “They’re all important,” point them to your very full
calendar, and ask again. Often, but not quite always, at this moment
you’ll see the facial expression of someone getting a clue.

• If they do volunteer something they care about that can be lower

priority, do your best to accommodate them exactly as they suggest.
This is not the time to negotiate further. The more compliant you
are with their concerns, now that you’ve set the limits in which they
can articulate them, the better the relationship you’ve created for
every time this happens in the future. (In truly ideal cases, this
becomes your reputation, and people know to work with you this
way before a conflict occurs.)

• Finally, if the deadline arrives and you’re juggling multiple due

items, make these the ones you don’t miss. You have a strong self-
interest to be reliable, for the same reputational reasons.

Don’t Accept “Work Harder” as an Answer

Of course, I’ve skipped the most obvious way people deal with the
above: they work longer hours. Whatever it takes to keep people
happy. Can you see now why this is a horrible way to handle this? Let’s

• Since you haven’t articulated any of the above to anyone, there is

zero cost for them to keep putting more weight on your shoulders,

or reason to think twice about how much weight any given item
might be.

• Even worse, some of these things will arrive in the form of new
recurring tasks, or additions to your job description. That’s more
time on your schedule for the lifetime of your position.

• Fairly often, people just work more, and don’t even tell anyone they
have. You send off that email at 10:30 P.M. and hope your corre-
spondent notes the time you’re working, and is maybe grateful for
it? How, exactly, does that discourage future 10:30 P.M. work ses-

• Finally: this doesn’t solve the problem. You can make a 40-hour
week into a 60-hour week, and again into 80, but eventually you hit
your ceiling. When you do, this will continue to happen. You have
to figure this out, and have uncomfortable negotiations, sooner or
later. Do it sooner.

Web content: This also applies to how people manage their time off
work, which I discuss in How Not to Take a Vacation.

I could have written an entire book on this topic, and I say that because
there are entire bookshelves filled with those books. These techniques
will require a great deal of thought and tailoring for the people you’re
applying them to. I don’t recall where I heard it first, but the best
advice I’ve heard about this: you don’t manage people efficiently, you
manage them effectively.

But sometimes you don’t. Sometimes all of your planning and strate-
gies can fall down and go boom. That’s when the next chapter comes
in—but do read it now, so you’ll know what to do then.

Handling “Work Harder” Situations
That said, sometimes you do work harder. You have a stake in
getting the project done quickly, or you want to impress people with
your extra effort. Renegotiating is your typical approach. For the
✦ Set the End Date: If it’s going to be exceptional, it has to be
temporary. Make that clear. Get detailed information about what
the project’s deliverables are (whether or not you’re directly
involved in them), when they’re scheduled, and the cutoff date
when things go back to normal. Just asking those questions
signals “this is not my new normal.”
✦ Re-prioritize: You might have to work harder for the new thing,
but that doesn’t mean you have to keep your usual agenda as full.
Maybe there are recurring tasks that can happen less often for a
while. Do not automatically take that time from your personal life
to give it to work. You can decide to, if you like. You can also
decide that some aspects of your personal life outrank some
aspects of your work, and act accordingly.
✦ Get compensated: You have a contract with your employer (or if
you’re independent, your clients and customers). It’s a legal
agreement. Depending on the work, it may be governed by laws
that supersede specific (and unenforceable) language in those
agreements. When you work harder without compensation, you
are treating your employer like a favored charity.
A few ways to get creative about this:
✦ Hourly employees: Know the laws regarding overtime, and get
paid properly.
✦ Contractors: You might be stuck, but you know better for next
time. Amend your future agreements for higher rates for rush
jobs, or added hourly fees when a project with set fees expands.
✦ Salaried employees: Maybe you can’t get paid more, but there
are other benefits that can be approved. Comp time, work-from-
home flexibility, or give-and-take on something benefit you care
about that you haven’t previously been able to get.
Don’t blindly work overtime—or your peak sustainable effort—purely
for goodwill, unless goodwill from that person is worth something.

Fail Successfully
If there’s one thing that’s frustrated me from reading dozens of pro-
ductivity books over the last two decades, it’s that no one told me how
to fail.

Failure is common when you start a new system. What I’ve written is
the first time I’ve seen a framework for transitioning from old to new,
and the reason it’s here is because it’s a common time to fail. But it can
also happen anytime afterward. Maybe your system has become much
less efficient. Or something specific derailed you, and you’ve stopped
reviewing it, referring to it, and updating it. I’ve read platitudes for
how to deal with that, but never techniques.

The corollary is that nearly every productivity author has presented

himself as the Platonic ideal of hitting deadlines and mastering New
Year’s resolutions. I don’t know about you, but the message I took
away from such writing was, “Well, it worked for him, but I guess I’m
just not good enough, or somehow negatively exceptional.”

I’m not going to do that to you. The advice I’ve given here, more often
than not, regards techniques I’ve learned precisely from repeated
failures, and often switching my system wholesale. Meanwhile, writing
this book was its own derailing event for me. It’s a huge task, parts of it
took longer than expected for reasons beyond my control (although
they were mostly my fault), and as a result I regularly blew off my
system far more than is my usual.

Note: That said, writing this book has also improved my system and
my habits, because it made me focus where I wasn’t taking my own
advice. You may never write a book, but if you can find your own
methods to give it this kind of attention, I recommend it.

It’s almost inevitable. At some point, you’re going to go off the rails.
Accept it now, and you won’t castigate yourself for it later. Come here
and let this chapter point you back to smooth running. (Give it a read
now, too. Can’t hurt to be prepared.)
Recognize Your Major Triggers

Earlier, we discussed why you should Have Triggers that draw your
attention to specific problems. The ones I’m discussing here are big
kahuna triggers; minor triggers tell you when to make tweaks and alter
small habits, but these major ones tell you something larger has gone
wrong, and you’re not going to fix it with tinkering around the edges.
Some possibilities:

• A huge project landed on your desk, and it’s made a pile of behav-
iors that used to work great for you less than ideal.

• You realize that you’re working off a legal pad, and you haven’t
launched your task app for two weeks.

• Someone important to you calls you on the carpet and tells you how
they perceive you’re screwing up.

• Your Past Due list looks like Figure 19 (in which the red 87 repre-
sents your Past Due list) and you’re pretty sure everything you
didn’t get to was a hard deadline.

Figure 19: The OmniFocus Forecast view counts upcoming due

tasks and everything past due in a calendar layout, a convenient
feature when you don’t see terrifying Past Due lists like this one.

It’s up to you to decide what’s a minor trigger that indicates the need
for a new practice or habit, and what’s a major one that tells you to
take a more holistic approach. I find the easiest one is, “are you miser-
able?” The more emotional impact this is having, the less rational

you’ve been about adjusting to it (unless you are very good). Emotions
are, if you will, a trigger that informs you about your triggers.

When you hit a major trigger, here’s what to do first:

• If it’s your first time here, start a new list of notes. No tasks here, it’s
pure documentation. Write down how you’re feeling, what’s
changed for the worse, and if you can identify them, the downward
steps that you took from “doing well” to here. Put these notes
somewhere that you’ll never lose them; your task app is a good

• If this has happened before: breathe. You have experience with this.
That might make it easier this time. Take out the notes you made
last time, and read them to see if they remind you of anything you
can do to make it easier this round. Then start a new set of notes for
this time, and put them where future-you will your entire history

It is entirely possible that you found this to be emotionally taxing. If so,

take a break. Seriously. It could be an hour, or it could be a week.
Come back with a clear head. You have official permission to take care
of yourself before you get organized. (You shouldn’t need it. Most
people do anyway.)

Crisis? What Crisis?
There’s another possibility: your issues are simply mechanical errors,
and you just stopped using your tools without a crisis or major
changes. This is more likely if your system never quite clicked, as it’s
easier to get knocked off that course. You could go back to Get
Started with Your Task App to see if you’d make any different deci-
sions now. But maybe stay here instead, as that’s also a step you’d
take here. Some of what applies in a crisis could be useful to you.
However, if your system worked for you for a while, your productivity
changes are far less likely to be a purely mechanical problem. Being
more functional and less stressed about things is more pleasant than
the alternative. Your system caused you to have new habits, and if
they worked for you, they became… well, habitual. There’s an inertia
to that, and it’s unlikely that it was broken by something minor. More
likely, something changed in yourself or your environment, in a way
you didn’t notice.
Big changes can be subtle, especially if they’re gradual. But if you’re
right and it was nothing in particular that got you here, these steps
will work for you regardless. Skip what’s irrelevant. Just be pretty
certain it actually is.

Identify Your Situation

When I finish this book, my professional life will go back to normal.

But before each of my parents died, that was a chronic situation that
lasted months the first time, and years the second. If a derailing event
or change involves your own health, or a something else major such as
becoming a new parent, it could be permanent.

It could also be entirely internal. Something changed about who you

are, maybe in a profound way, and this is the first time you’ve noticed.

Web content: You might consider whether this could be the onset of
a mood disorder or mental illness. No one naturally starts with the
ability to recognize mental illness the first time they experience it.
Getting sick can feel like normal. Understanding this, and when to get
help, is discussed in great detail on the blog: You Can’t Fix Your
Mental Health with Tools.

Note what changed. It might even be what’s going to change; many

expectant parents are not exactly of sound mind before the birth.

If the situation is temporary, you have the option of limping along until
your life resumes as it was. All you have to do is decide whether major
changes in approach will improve your mood and abilities in the
interim. Usually, it’s worth the effort; the more you “just can’t even”
with your situation, the more valuable such changes may be.

If you’re not sure, read through the rest of this chapter, roll the ideas
around in your head, and do what you think will work best.

If it’s permanent, you’re foolish if you act as if it were otherwise. You

designed your system for a life you’re no longer living. Of course it’s
inadequate now. It needs revision, and the sooner you can do that, the

If it’s the kind of crisis where you have no idea how it’s going to go: not
a bad idea to take your best guess, and also have a few strategies at the
start for what changes you might make if it turns out to be longer than
expected. The moment you learn it’s worse than you thought will be
emotionally difficult. Having your checklist ready—and nice, distract-
ing tasks on it to make you think about something else—is a gift to that

Note: If your situation has a fixed ending, but that’s a long time

away, treat it as “not sure.” Limping along is only suitable for short

periods of time.

Keep Your Priorities Straight

Something happened to get you here. It might be a crisis. It’s likely the
most important thing on your plate, otherwise it wouldn’t have had the
emotional heft necessary to change so many of your good habits.

That comes first. Reorganizing comes second, except insofar as it helps

you deal with it. Everything else is third.

Note: That’s an elastic definition. If “everything else” means you

might lose your job and have a financial crisis on top of your existing
one, the need to avoid those consequences is an equal top priority,
and may require immediate changes to your system. What does not:
dealing with falling short in areas with only normal consequences.

You’re about to make another transition similar to (but maybe smaller

than) when you first adopted your system. Like last time, this will be
somewhat disruptive. When you can’t deal with that, put it off—unless
being back on track is now required of you to meet your new responsi-
bilities. If you’re feeling similarly to how you felt when you first adopt-
ed your new system, when being disorganized by itself was distressing,
getting organized again should come earlier on your agenda.

There are some crises in which it’s socially acceptable to fall apart a bit.
Only the worst bosses expect the same job performance from someone
who’s lost a loved one. Only the best understand that losing a pet can
feel the same way. When others may attribute the crisis to a choice
you’ve made—“laziness” due to ADHD comes to mind—people tend to
give you less slack.

Note: In which case, selfishly manage such people for your own
protection. If their opinions have consequences, what matters right
now are the consequences, not the opinion. Lessen them when you
can. Their opinions can concern you later, when you have room for it.
Exception: when your relationship is emotional, not professional.

There is one major exception to this overall approach, and that’s when
you’ve taken someone else’s crisis and made it your own. As with so

many other things, this is something you can decide to do. But if it’s
causing this much disruption, whomever may have decided for you has
now lost permission.

For example: someone quit at work, and you started working the
equivalent of two jobs to prevent the company from collapsing. That’s
great if it’s your choice. But if you don’t own the company, and you’re
collapsing, the prioritization problem is where you put yourself on the
totem pole. The default should be “you first.”

Anyone or anything that takes precedence: you put them there, no one
else may.

Start Over

As you might suspect, the next step is to Get Started with Your Task
App again, with a few modifications for crisis management. You’re
again transitioning from one system to another. But instead of old and
new, you’re transitioning from whatever it is you’ve been doing from
the moment you stopped using your system well. The system you’re
transitioning to is probably the same one you just left—this isn’t a good
time to make huge changes—but it may need some beveling of its edges
to accommodate your new situation.

Alternatively, maybe you’re using all the same tools and methods that
worked fine for you before, but it’s producing bad outcomes. That’s a
more subtle transition. You’re not going from one to another, you’re
figuring out what broke, and the series of changes and Band-Aids that
make it better.

The steps you took when getting started should work for you now, but
for different reasons. Then, those steps worked because they taught
you a new way of approaching your organization. Now, they work
because they draw your attention to the specific ways things went off
the rails, the old strategies that stopped working, and the new habits
you implemented unconsciously that didn’t help. (You may also have
some new good habits. Identify them and keep them. Make noticing

them recurring tasks, if you need regular encouragement: “Did you
take a walk around the block this afternoon?”)

Getting Started has modifications when it’s a reboot. What you do

differently this time:

• Some Get Started steps will be superfluous now, but don’t simply
assume they are. They can draw your focus in necessary ways. Give
each some consideration before you move on.

• Few people should swap out their tools right now, unless there’s a
blisteringly obvious reason to add a new one. Lean toward putting
up with more annoyances, and away from changes that may cause
more disruption. (Faster phone, good. Replacing the software you
know with something you’ve never touched before, bad.)

• Your original transition was geared toward what was then normal.
This is your new one, for now at least. It could change everything
from the timing of your daily habits to your overarching life goals.
Even if you’re staying in the same tools, anything that already lives
there needs some consideration, and that’s next.

Declare “Project Bankruptcy”

There’s a concept called “email bankruptcy.” It’s when someone

decides that they’ll never get to the 20,000 messages in their inbox, so
they hit “select all” and “archive” or “delete.” Sometimes people send
out a blast email when they do this, informing everyone that if they’re
still expecting something, they should email again.

“Project Bankruptcy” isn’t quite as drastic, but it’s a useful tool. Every-
thing that lived in your system before, pertained to your life pre-
derailment. Some of it’s relevant, some of it is now relatively less
important, and some of it has died of neglect. You have to pass them all
through a cheesecloth before they get to live in your revised system,
because something about them in aggregate caused you to stop ad-
dressing them properly when your situation changed.

I can’t tell you how to decide what’s still important, but I can provide
the mechanical steps:

1. All the projects and tasks you used to have? Put them in one big
folder, then put that entire folder “on hold” in your task app. This
shuts off all their notifications and deactivates every task. None of
them deserve your attention or time until you’ve decided individual-
ly which ones still do.

If your software doesn’t allow for one big folder, you can archive
your archive everything your task app contains, and start with a
fresh database. Two things first before you do this:

a. Check your software’s help to see how it deals with this kind of
archiving. Your old data must be readily available so you can use
it as a reference when you put some of it back. Some software
makes this a true pain in the neck, which is why the first thing I
suggested was one big folder in the existing database; if you do it
that way, you’re using your existing skills when you move things
around. An archival reference is new to you, and will be different
to work with.

b. Keep your existing structure, as that remains relevant. You want

your carefully curated contexts that used to fit you like a glove, as
some still will. If you have folders you use to organize batches of
projects, those are likely still useful. Think of it this way: you’re
throwing all your furniture in the yard to decide what you want
to keep. You’re not building a new house.

2. During the first Get Started, you gave early special attention to
everything urgent in your old system. This time, you give that
attention to your crisis or situation first. Addressing that is prereq-
uisite to literally everything else.

3. After that’s in your tabula rasa task app, do the same as before: an
urgency scan of your old projects and tasks, followed by recurring
tasks and sprints to process everything into your new one. This
time, it will be easier, as everything you’re considering will be

reasonably fresh or obviously moldy. You were more organized

before you got off track. That will make this time much faster.

However, there’s a radical difference in the approach you take,

depending on whether your new normal is likely temporary, or

likely permanent:

‣ Temporary: The major roles, life goals, and other Big Decisions
that guided your old system probably haven’t changed in their
importance, only in how they should be expressed at the project
and task level. Your filter should therefore be bottom-up, as
discussed earlier in Top-Down vs. Bottom-Up. You’re mostly
concerned about paring down time requirements, and extending
out old deadlines far enough into the future so it’s realistic you’ll
meet the new ones.

‣ Permanent: You’re never going to have your old normal back.

Maybe some of your roles and goals have a permanence of their
own, but all the ways you expressed them were in the context of
your old normal. As painful as it may be, some of your old-nor-
mal Big Decisions may no longer apply. Your filter is top-down.

‣ Not Sure: One of the above options will be less painful if you
turn out to be wrong. Do that one. Usually, switching from
permanent planning to temporary is a happy circumstance,
which lets you pick up things you thought lost forever. Switching
from temporary to permanent, on the other hand, can be a gut
punch for each thing you were hoping wasn’t lost yet.

Note: Maybe a middle ground. Plan for the worst, but have a
sketched outline of what else you’ll do if things are better than

4. When applying this filter, bonus points to anything you enjoy doing,
or that recharges your batteries. Major points off to anything that
taxes you. You may need exceptional strength to deal with your
situation. Be exceptionally kind to yourself.

5. Don’t skip the management tasks you set up the last time: you still
need pointers to check your collection points, review alerts, and
everything else you once used to keep it all humming. But if any of
these seem irrelevant or unrealistic now, give them a trial run, and
dump them if they’re part of what stopped working.

6. Re-adopting your system is going to change some habits you built

when you were derailed; that’s uncomfortable, but completely
expected. But definitely note excessive friction or resistance to using
what you just rebuilt. That implies that something that broke your
old system may have been accidentally added to your tabula rasa

When faced with crisis, we seek routine. When confronted with

enormous change, we attempt to minimize it. When you resumed
planning, you may have been thinking too much about your old
normal, and didn’t change enough for the new one. Do what it takes
to make the rebuilt system comfortable first. After that, you can
shoot for more productive.

Reviewing your formerly active projects to see what should be included

now may be difficult. If you seriously diverged from your one-time
plans, or if it’s been a long while since you were last here, you’re going
to see many things that went fallow. It can feel like a personal roadmap
of recent failures. Give yourself a moment to accept that. Then com-
pare it to your notes from earlier, and say, “This is why that happened.
It was situational. It doesn’t have to stay this way.”

The easier part: all those things that expired? They’re done. Mark them
completed or dropped, and all the things they required you to do are
gone. A potentially substantial chunk of your time and effort has just
been freed up for other things.

Note: If you’re off the rails emotionally as well as organizationally,

you may need reminders to do things you used to do automatically. It
might embarrass you to need them. Remember: this is private and
personal. Let your system remind you. The habits will come back.

Keep More Notes

As you get back into the swing of using your system again, you’ll also
be mapping out the parameters of your new normal. Right now—when
you’re getting restarted, and you’ve just taken the initial steps after
noting you were derailed—you may think you know what’s coming up
next for you. But that’s the thing about the “new” in “new normal.” One
way or another, you’re proceeding into uncharted territory.

You’ve dropped what’s no longer relevant, and you’ve added your best
guess about how to manage. But it’s only a guess. It’s less likely to be
accurate than anything you might have experimentally added to your
system in what you used to call normal times. But you can’t guess any
better than that.

The way to deal with this: take more notes. Write down everything
that might be relevant. Keep more narratives. Document your tasks
more thoroughly. Start a diary. Pay close attention to what’s changed
about you, your habits, and your emotional cues.

There are a few reasons you’re doing this:

• Much of what I’m telling you to write will live in your head in a
vague way, until the moment you set them into words. Writing it
down is telling yourself what you think. You may write something
and realize, “No. That’s wrong. That’s what I’m supposed to think,
not what I do think.”

• You need new strategies, habits, and approaches to inform the

specific changes you’re making to your system to accommodate
your new normal. Turning vague thoughts into words, and having
them in a reviewable format, is the best way to also get you thinking
in those terms.

• People derail all the time. It happens to all of us, and it happens
more than once. You’re also writing this documentation for future-
you, and it will make your life easier when you’re that person.

Review and Generalize

When you get back into the habit of doing regular reviews, you also
review all the documentation you’ve generated while failing successful-
ly. Keep the time you spend here brief enough so it doesn’t delay or
derail your review, but when you can make the time, inspect it closely.

What you’re looking for is evidence and data points to tell you what’s
working. You may notice a marked improvement in your mood be-
tween a few weeks ago and now. Your writing could be better, less
disjointed, more focused, or more descriptive. (In my case, when I’m
dealing with an emotional crisis: fewer profanities and less anger.) Try
to draw correlations between what you did, and what noticeably
improved. It likely was not noticeable at the moment it happened, but
maybe it’s clear now.

Then extrapolate from those specifics to a general category they might

reside in. On the day you sat outside in the sunshine, your evening
notes were far sunnier as well. Perhaps you need to get outside more?
Or maybe the key thing for you was that you took an hour and stopped
worrying in a way that you haven’t in weeks.

Once you have generalizations, try out a few more reminders in those
areas. Take good notes here as well. This time, you’re figuring out what
works for you. If you’re ever back here in the future, you’ll know at the
beginning how you took care of yourself now, and will have known
behaviors you can resume to improve that situation.

Transition to Normal

In a temporary situation, some of the above steps are highly abbreviat-

ed. You won’t have spent nearly as much time, effort, or brainpower
making changes. But you will have made some, and when your tempo-
rary situation is over, you should review them to see if they should be
dropped as no longer necessary. Some of them will be situational, and
now obsolete. But for anything you discovered that made your life

better (or just made difficult things bearable), maybe you adapt them
to better times and keep them.

For longer-term issues, you’re not transitioning back to your old

normal, you’re acclimating yourself as best as you can to your new one.
But you may still have approaches and behaviors that were suited only
to crisis onset, or to defining your new ongoing methods. These can be
dropped once you’re feeling… well, if not as in control as you once did,
at least as close to that as you think is possible.

Frequently, people respond to adversity by just getting used to it. It’s

unconscious, and hence can lead to new dysfunction. You’re going to
do it with deliberation, and as a result, with far better outcomes.

Reward Yourself

No, really. Look at what you accomplished: You took a crisis and made
it manageable. You were more on top of it than your default would
have been, in the absence of this effort and attention. You took care of

Most important, you made it through. If it’s not over, it’s now normal.
No matter what, you are better prepared than 95% of humanity for the
next crisis, because you so thoroughly understand how you acted and
felt during your last one.

That is a huge accomplishment. Give yourself full credit, then take a

break, make space, and do something you enjoy. Make it the most
important thing you do for a while. Let it be as memorable a year from
now as your crisis will be.

Understand Your Brain,
Understand Your Body
Most people who know me would call me the worst possible apostle for
effective health management. Suffice it to say that I am not a member
of the “my body is a temple” community. I am, however, a strong
proponent of using the best tool for any given task—and to state it
reductively, your body is the first tool that all other tools rely upon.

This gets into surprisingly difficult issues. I can think of many things
that may be good for productivity while being “bad for you:” an after-
noon energy shot, a cinnamon bun that lifts your mood, a cigarette, a
metric truckload of caffeine. It’s not an either-or situation; some of
these might work well for you and also not be the best idea.

Note: It’s not only that it’s bad for you, it’s also putting up with

everyone around you somehow thinking you need to be told it is.

Endlessly. This is an area where everyone feels free to judge and no

one believes you rationally arrived at your choice.

As you read this chapter—meant to be an Owner’s Manual for Your

Body as a productivity tool—you should make explicit choices, and
figure out your own balance. A fair amount of advice here is to take
better care of yourself. But some isn’t, and this book isn’t titled Take
Control of Leaving An Attractive Corpse.

Experiment on Yourself

Your body belongs to you, and you should treat yourself like a scientific
experiment. Change the inputs, and you’ll change the output; some
inputs that seem extremely minor can affect you in profound ways.

Note: For example, a true and unbelievable fact: normal air at sea
level is a mild narcotic. At higher altitudes, everyone is slightly
smarter. Not that this means you have to move to Denver, mind you.

There are several inputs that are obvious to everyone: sleep, diet, and
exercise are the ones we talk about most. There are many others we
don’t notice, possibly because they’re mostly beyond our control: air
quality, how much sun we get, ambient temperature, or whether the
times we eat are actually in accordance with how our blood sugar levels
are varying. When you feel hungry enough to notice, you’ve actually
been hungry for a while, and during that time you’ve made different

Note: A study of parole decisions discovered that almost no paroles

were granted immediately before lunch, but the rate rebounded after.
Consider this the next time you’re making big decisions at 11:30 A.M.

So what you do is vary one thing at a time, and track whether it makes
a difference for you. Things to track: your mood, and your work quality
and output, as in Figure 20. These things are not the same, and
neither one is more important than the other until you say it is.

Figure 20: A slightly fictionalized measurement of a week in my life.

Note: I’m using a Likert Scale from 1 to 7 for mood and output,
because that’s what I was taught to use in grad school. It provides
better data than 1 to 5. I’m also roughly assigning values with a bell
curve, so 1 or 7 means truly awful or phenomenal.

Some changes won’t make an obvious difference, and some may seem
life-changing. Most often, you won’t be able to tell. Give them all a
week or two. This is partially because you simply can’t trust your
immediate observations, in much the same way that any new diet that
makes you shed water will seem to work quick weight-loss miracles.
The other reason is that after two weeks, if the effect is positive, you
only need a week or two more before it becomes a habit. You’ve already
done the hardest work of forming a new habit, in the spirit of being
your own lab rat.

Try These Changes

My choices won’t work for you, so I’m not going to tell you what to do.
Instead, these are categories of changes you should consider. What you
actually decide should be entirely determined by what “improves” you,
where you define the parameters for what’s considered an improve-
ment. (I can’t stress enough: your parameters, not what everyone
around you thinks you should do.)

Hands down, move your body as often as you can. It’s good for you on
nearly every measure any scientist has ever invented. You may or may
not get productivity benefits from it. You’ll often hear people saying, “I
get so much energy from my exercise!” Great for them; for me, exercis-
ing makes me tired, and tired makes me stupid. That doesn’t stop me
from experimenting to find new approaches that don’t.

Figure out something to do, and do it whether or not it improves your

work. It’s more important than simply getting more done. That said,
it’s a perfectly sound decision to stick to only the methods that improve
or are neutral to your productivity, so long as you don’t ditch them all.

There’s a weird backlash against caffeine that is entirely out of propor-
tion with its actual health impacts. I suspect this comes from the

“health is everything” crowd, who don’t much care which “chemical”
you’re putting into your body—they’re all bad.

Note: Everything is made of chemicals, including you. And kale.

Caffeine is perfectly safe for people in normal health, in quantities

including large amounts of strong coffee. It’s downing caffeine pills
and those two-ounce energy shots that can give you a toxic dose; use

Note: I take Ritalin for ADHD, and speaking only for myself, energy

shots have more effect on me than prescription speed. I avoid them

because they work too well. Scares me a little. Just mentioning,

should your experiments lead to using them regularly.

This is your call. In my opinion, the quality of life that comes from a
preferred diet possibly outweighs the health impacts of a proper diet.
From a productivity standpoint, yes, what you eat for lunch has a far
bigger impact on your afternoon than you realize. But diet modifica-
tions for productivity have to be very closely measured to be accurate.
This is something I think is more important to calibrate to personal
satisfaction, rather than some utopian health maximum.

As with exercise, this is something you put into place for a while before
you see any benefit. But if you cut down on heavily caloric lunches, you
should get an immediate result; food comas are a real thing, and
there’s a reason why it takes all Thanksgiving weekend to wake up after
Thursday overindulgence. Try a lunchtime salad, and see if your
afternoons improve. Alternatively, if you eat an uberhealthy diet and
feel awful and exhausted by noon, maybe try a bit more junk.

Note: If you’re healthy and on a strict diet for some kind of weight
goal: is that really your most important outcome right now? It’s fine,
but don’t give it automatic priority unless there’s a health outcome
you need from it.

You need more.

Okay, I’ll expand on that. Believe it or not, a few of you are getting too
much sleep, and it’s adversely affecting your work. Some people, but
not many, physically need ten hours a night. But if you sleep a lot and
you frequently wake up tired or groggy, that’s usually indicative of a
physical or mental health issue. If you wake up refreshed from a long
sleep, “a lot” could be how much you need.

Web content: Every year, around 1 in 12 Americans experience

clinical depression. Awful sleep habits are a common symptom. This
and other mental health issues are discussed in You Can’t Fix Your
Mental Health with Tools.

Some of you are perfect. You get what you need. Maybe that was a
deliberate choice based on paying attention to your body clock. Maybe
you just got lucky; folks who need less sleep tend not to notice any
difficulties. But people who do need more than they get also don’t
notice, because deprivation has become their baseline. Nearly everyone
thinks they can “get by” on less sleep. Psychological and physiological
testing says they’re wrong.

If you’ve never measured your sleep consistently, you’re almost cer-

tainly wrong about how much you’re getting. It’s also possible to be
unconscious but not getting any sleep benefits for part of the night. (If
you want to create these conditions for yourself, just hit the snooze
button; the interruptions ensure that you’re getting zero benefit from
those extra minutes.) A smartwatch or other monitoring gizmo can
help; there are also apps that measure your sleep habits when you put
your phone on the corner of the mattress. Or make a daily note of how
long you’re in bed, and your sleep hygiene (that is, how long it takes
you to fall asleep, and how long you stay in bed after you wake).

Once you have these numbers, analyze them. If you regularly get little
sleep weekdays and “catch up” on weekends, you’re sleep-deprived, full
stop. Experiment with not doing that, and see what happens. Likewise,
if you usually average eight hours, but this past month you had six,
give some thought to whether that month was “good” or “bad,” and if
that could have been affected by a cognitive deficit you didn’t notice.

I understand that many people simply cannot go to bed earlier or wake

up later than they do, due to work schedules, children, social lives, the
lure of the Netflix queue, the need to milk Bessie before she wakes up
the goats. One possible solution: nap time, milk and cookies optional.

Find a Place to Sleep

In my opinion, there should be an international campaign to promote
the cultural acceptance of the afternoon nap, both in the workplace
and elsewhere. Countries that do have the right idea.
I find it bizarre that, for many people, naps are out of the question
because there’s nowhere to sleep. Even in many public parks, or the
driver’s seat of your parked car, police or private security will tap you
on the shoulder, or on your window, for reasons that baffle me—who
is being harmed?
If you park in a private lot, have a chat with the security guard, and

it should be no problem to grab a catnap. The main issue is getting

your coworkers used to your being away from your desk for 30


Sometimes you have to get creative. Historically, the only place I

know where napping is allowed is Starbucks, so long as you’re not
drooling on the table—but recently the entire chain changed policies,
so you may need to find a store with lax enforcement. Buy a coffee—
it’s the social contract for renting the table for an hour—and put it
prominently on your table, then make sure you’re napping as unob-
trusively as possible. (Knowing the baristas by name goes a long
way.) Libraries are also sometimes good. When that’s not an option,
board public transit that travels a short loop, and set a watch or
phone alarm. When you wake up, you’re already on your way to
where you boarded, and people rarely bother someone sleeping on a
bus or train.
This is ridiculous. You should be able to tell your boss, “I get more

done when I stay 30 minutes later and take a nap at 3 P.M.,” then

sack out on a couch.

When you sleep is as important as how much you sleep, so track that
too; it’s better when the sun is down (or in rooms with excellent light
isolation), and it’s better with reasonably consistent times day to day.

Everything Else
There is no limit to how many ways you can experiment with your
habits, and possibly develop better ones. (Again: “better” as you define
that.) I could extend this chapter with discussion of what you do in the
morning versus the evening, or what music you listen to and when, or
how you feel after social activities.

I deliberately avoided the can of worms that is alcohol and (other)

recreational drugs, because there’s nothing I can say that wouldn’t
sound preachy to half of you, and overly permissive to the other half.
I’ll just say this: if you do stuff to your head, pay attention to what
happens when you do, and for a while afterward.

Good luck, get creative, then meet me at Starbucks for a nap or an

espresso. I’ll probably be on my fourth cup of the day.

Consider Everything
After a while, it’s a good idea to take a step back and consider… well,
like the heading says, everything. In fact, you want to do this repeated-

You have a few choices about what conceptual altitude to take when
you do this. If you just got out of college, it could be a big deal to plan
out a year in advance. If you’re feeling a vague sense of dissatisfaction
with life in general, you might want to map in broad strokes from
tomorrow until your eulogy.

It seems to me that most people should visit both extremes, and a few
touchstones in the middle, from time to time. Speaking for myself,
thinking about what I want to do with the entire rest of my life scares
the willies out of me—which is fairly good evidence that I haven’t
thought about it enough. Do what’s comfortable at first, but push
gently against your boundaries from time to time.

Note: This is also the time to revisit some assumptions, especially

old ones you’ve never articulated. Are you living up to your goals, or

someone else’s? If they’re yours, how long has it been since you

chose them?

The following time periods are guidelines, not rules. Adjust them based
on how quickly you acclimate, how well your system is working, and
how rapidly your bigger picture changes. As you read this chapter, set
up tasks that point you back here, to each section as their time period

The First Month

There is one instruction on what not to do, and that’s make any large
decisions about your new system.

Consider a New Year’s resolution to “get healthy.” That’s huge. It
includes better management of your health care, eating better, exercis-
ing more, cutting out bad habits, and basically modifying every waking
hour of every day. You don’t do that all at once. By February, if you’ve
broken the habit of having a hot fudge sundae for breakfast, you’re
ahead of the game.

Same thing here. Your resolution is to “get organized,” or “reach my

goals,” or “be less stressed.” Your system, your task app, your circum-
stances, and you are all large moving parts. All you’ve had time to do
so far is identify and fix a few small habits.

The problem right now is category error. Almost no one faces the
problem of “I didn’t get healthy” and decides, “Okay, I’m just never
going to get healthy.” But right now is when plenty of people either
spend another three months picking out software, or decide that
they’re genetically unable to be organized. Both are bad ideas. Don’t
abandon your system now because it “doesn’t work.”

Right now, you’re spending the maximum amount of time you’ll ever
need to manage your system. You’re paying attention to things that will
become automatic. You’re thinking harder about everything. And the
biggest benefit that’s supposed to come out of it—getting more done,
giving yourself permission to be human, and making realistic assess-
ments about how balance those together—you’re not used to doing
those things yet.

Stick to small changes. You have permission to go bigger in only one

case: when your prior choices are actively and obviously detrimental
in ways that I haven’t said will automatically get better. If that’s hap-
pening this early, go back to the beginning and start over with better

If you don’t need that kind of wholesale revision, don’t revise at all.

After Three Months

It takes two to four weeks to form a small habit. It takes months to

form larger habits that have small ones as a prerequisite. That’s around
where you should be by now regarding your system. Some of your
pointers are redundant, more things are in muscle memory, and
during your regular reviews you’ve tightened things up and sanded
down rough spots.

Now you can look at some medium-sized pieces, including your task
app and the other apps and tools you use, if it’s still eating too much
time and you’ve learned all the preferences and modifications that
you’re ever going to. If you do switch, don’t start from scratch; figure
out what methods and approaches have worked for you when the tools
didn’t, and re-implement them in the new tools.

This is also a good time to tackle the life changes we discussed in

Understand Your Brain, Understand Your Body. If you’ve already
started sleeping better, congratulations, but you’re a true unicorn.
Everyone else has put that off until later. Now is later.

Six Months or So

Congratulations! By getting here, you’re already doing better than

nearly everyone who’s ever cracked a book like this one. You may not
have the best small and medium habits, but you’ve developed one big
one: you’re approaching your time systematically. It’s not a question
now of whether you’re going to organize yourself, it’s a question of

That’s a big deal. Reward yourself—and do so regardless of whether

you’re “doing enough.” If you’ve seen only small improvements, you
have the wrong system. So long as you don’t ditch the concept of
systems—and when you’ve drifted into older habits, you’ve managed to
Fail Successfully—you’re doing much better in ways you likely haven’t

Now you have the experience to make larger changes to your system if
you feel the need. You may also have some really big changes identi-
fied about your life in general, that you think you need to address.
You’re just about ready to attempt that, but do you want to do that
now, or will you be better prepared later, with some more time under
your belt?

If the answer is “obviously now, yes, I can’t wait,” jump ahead to Are
You Rereading This Book?

Everyone else: make projects to consider and implement the changes

you want for your system. Schedule additional time for them accord-
ingly, and like every other time you’ve worked on managing your
system, keep an eye on whether you’re still accomplishing enough of
everything else. Deliberately dropping a few projects, and extending a
few deadlines, is a good idea to make room for this. With any luck,
you’re in the habit by now of adjusting as needed, and have a few
successful strategies for doing that.

A Year or Two

Again, congratulations for sticking with it. This is as big a deal as

getting an annual gym membership, and being in the 10% who actually
use it. Well done.

By now, your goals have shifted (probably unconsciously), your cir-

cumstances have changed, and your attitudes are different. If having a
system stressed you less, you might have since decided that lower
stress is a good thing in and of itself, and should take precedence over
what you earlier considered to be top goals. Maybe you’ve gotten into
the habit of letting additional free time from being more organized
become unstructured leisure time. Or maybe you’re still aimed at being
a productivity machine with any time freed up. Your choices.

That last part requires more thought. One other thing has happened:
your body has aged a little, your peak sustainability has altered a bit,
and unless you’re good at listening to your body, you likely haven’t
noticed. If you’re young, you’d probably need a microscope to measure
the difference. If you’re, uh, not so young, it starts to happen dramati-
cally. By now, I hope you’ve learned not to try to “power through it.”
That’s never sustainable.

Go ahead to the next chapter. It’s time to take another spin through
this book; a quick skim is fine every year or two, but a thorough reread
is called for less often. You should clarify everything that’s been uncon-
scious until now, set new directions and new goals, change what’s not
working, and concentrate on getting the most of what does. Or you can
decide that it’s all good, in which case, now’s when you decide that and
know it’s the right choice, rather than proceeding out of inertia.

If you make any major changes, you’re resetting the clock on this
chapter: go ahead and set new one-month, three-month, and six-
month reminders to come back here. If all is well, or mostly so, set
another year-or-two reminder.

What you’re doing right now, this big-picture thinking? It never stops,
and that’s a good thing. Looking back on where you’ve been and how
you’ve improved, and choosing where to go next, should recharge your
batteries. If it doesn’t, that’s a trigger that you’re making the wrong

Are You Rereading This
There are three categories of people reading these words. Each of you
get different instructions.

New, and You Read the Entire Book

That’s a good habit. Only a few more pages to go. You’re in much better
position to make the right choices now, because you know what’s
ahead, and you have more information about what to avoid. Keep
reading about what you’ll be doing in a year or two, and if that informs
the decisions you make now about how much you document with
future-you as your audience, all to the better. Good luck!

You’re Confused About Something

When you’re learning new skills, it takes a while to fully grok them.
That word comes from A Stranger in a Strange Land by Robert
Heinlein. It means to truly understand not only everything about
something, but also the reasons why it is the way it is, and its purpose
in existing. Spouses and old friends, if they’re very attentive, very
diligent, and a little lucky, grok each other. I love this word.

Cracking the book again is an instinctive move, and it’s a good one.
Reread anything that’s not clear, but you don’t need to go over every-
thing again. See the previous chapter regarding how long it’s been
since you got started; if it’s early days, it’s counter-productive.

But for some of you, it just doesn’t work, even after multiple sittings.
I’m expert, not omniscient. Here’s what to do next.

Read Books and Hit Websites
There are dozens of other approaches that are somewhat or wildly
different from what I’ve presented here. Find a few more. Where my
specific steps haven’t worked for you, the overall structure and ap-
proach still will. Most of the books I’ve ever read about productivity
had fantastic conceptual ideas, but very little worthwhile about how to
implement them. Hopefully, your time here has been good training for
coming up with your own tactics for a new strategy.

Web content: I’ve included a bibliography of the best books I’ve

read, with capsule summaries to let you know how applicable they

are for you personally. I am extremely fond of the Bookworm pod-

cast, which reviews a new productivity book every two weeks.

If you’re not entirely sure whether productivity is the real problem, but
is masking something else, skip the productivity books and look for
some about what to do with your life from a broader perspective. There
are options for everyone, from college kids to retired people, the deeply
religious to the atheist, the folks who focus on small communities and
those who take a global view. Figure out what fits, and then come back
to making a productivity system.

If the above steps are too much (or too time-consuming), Google is
your friend. There are plenty of essay-length articles, even whole
websites and magazines, dedicated to publishing articles about produc-
tivity. It’s an easier buffet of options, more of a tapas menu than five
entire meals. (I personally like Lifehacker, but it’s also full of fluff; I
just lost 15 minutes reading about a cheesesteak casserole I might have
to make someday.)

There’s one more category of information to consider: productivity

forums. You’ll find these on websites, Slack channels, email lists, and
probably a local Meetup every month or so. Everyone there has their
own experiences and insights, and can prevent you from repeating
their mistakes. You’ll meet many people who are certain that their
methods are the One True Way. Get suggestions, not rules.

Note: After you have enough experience, that applies to my rules
and recommendations, too. You define “enough.” Everything here,
I’ve included because it would have saved me tons of effort if some-
one else had years ago. But you keep only what works.

“This Just Isn’t Me”

I’ve written this book to be universal. What’s here is what works for
most people, most of the time. But that’s “most,” not “everyone.”

I’ll let you in on two secrets I knew when I started writing. The first: for
a small number of you, none of these specific approaches, tools, imple-
mentations, or daily methods will work for you. I couldn’t tell you that
earlier. Had you seen that in the introduction, you might have given
up; people for whom this book did work would have, too. Many people
think they’re incorrigible until proven otherwise.

The second is the good news: I made this universal by teaching you
things when you weren’t looking.

Once you’ve read this book, tried it out, and learned the large and
small ways it doesn’t fit you, you’ve also learned the process of how to
build your own. Reading this book is the outline for writing your own,
if you have to. Everyone needs an approach, everyone needs tools,
everyone needs implementation, everyone needs to review, and every-
one needs to align the whole shebang with bigger goals. Not everyone
does it in that order. Not everyone will find particular specifics that fall
under those categories worthwhile. Most people learn from more
reading—but a few go to monasteries.

You needed the experience of not fitting to know what to do next. Give
it a little longer, read other books, and dive in as much as you can. If
you’re wrong about being the rare exception, and someone has already
invented your particular wheel, you’ll save yourself a lot of trouble.

If not: write your own book, in whatever format works best for you.
Could be a diagram on a cocktail napkin. Could be five years of diariz-
ing, after which you understand yourself well enough to form a system
around you.

There’s a saying among scientists: “There are no failed experiments,
only those that further proved what doesn’t work.” You haven’t wasted
time and effort (in my opinion, and I hope you agree). You’ve defined
your parameters for future success in greater detail than you’ve ever
had before.

It’s Been a Year, My Reminder Sent Me

It’s time to go back to page one, skim what you think you know, and
maybe read in a bit more depth what you glossed over last time. You’ll
do this with all the experience you’ve had since then; it will make more
sense, and your own implementation ideas will come more easily.

Remember all those homework notes you took in the first few chap-
ters? The ones half of you skipped, or skimped on, because they didn’t
seem relevant? Get them all out, as well as any notes you’ve made to
yourself since then. Read them all in chronological order. You might
discover gaps, where you wish past-you had been more thorough,
because it would be useful now. Fill those gaps for next time as a favor
to future-you, because you’ll come back here in a year or two.

Constant self-improvement, always knowing where you’re going, and

being happier all along the way. Put those on your to do list.

About This Book
Thank you for purchasing this Take Control book. We hope you find
it both useful and enjoyable to read. We welcome your comments.

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About the Author

Jeff Porten is a Mac and internet consultant, part-time journalist, and

sometime writer of books in Philadelphia. He is previously the author
of The Twentysomething Guide to Creative Self-Employment, a title
that amuses him greatly now. He is probably at a Starbucks with his
MacBook Pro and a gallon of coffee, doing his best to practice what
he’s preached.

Adam and Tonya Engst did me a solid by creating Take Control Books
and making ebook writing easy. Joe Kissell did likewise by buying this
one, and putting up with more tsoris than he expected. Thanks to my
advance readers and people who helped in other ways: Josh Centers,
Michael Cohen, Adam Engst, Tonya Engst, Brian Greenberg, Morgen
Jahnke, Jason Koppel, Peter N Lewis, Lauri Reinhardt, Sharon Zardet-
to, and likely several Facebook friends I’m forgetting; special thanks to
Caroline Rose. Thanks to Steve Wozniak, Steve Jobs, and all the geeks
at Apple, for building most of the tools I use, and for inventing how I
make my living. Shout-outs to Stephen Covey, David Allen, and Neil
Fiore, for having the best ideas on productivity I’ve ever read, and for
being vague enough about how to do it to leave room for me. Warm
thoughts for my parents David and Lois for the usual reasons, plus
making me obstinate enough to be self-employed, which is how I
learned everything between these covers.

Shameless Plug
Have Mac, internet, or networking issues you can’t solve? Need better
tools, especially your technological ones? Want all that wrapped up
with productivity expertise and big-picture awareness of why you do
what you do? I’m available, and willing to travel. One-on-one training
and implementation, group seminars, office workflows, conference
presentations and speeches: tell me what you need, and we’ll figure out
if there’s a good fit. Reach me at takecontrol@jeffporten.com.

About the Publisher

alt concepts inc., publisher of Take Control Books, is operated by Joe

Kissell and Morgen Jahnke, who acquired the ebook series from
TidBITS Publishing Inc.’s owners, Adam and Tonya Engst, in May
2017. Joe brings his decades of experience as author of more than 60
books on tech topics (including many popular Take Control titles) to
his role as Publisher. Morgen’s professional background is in develop-
ment work for nonprofit organizations, and she employs those skills as
Director of Marketing and Publicity. Joe and Morgen live in San Diego
with their two children and their cat.

• Editor and Publisher: Joe Kissell
• Cover design: Sam Schick of Neversink
• Logo design: Geoff Allen of FUN is OK

More Take Control Books

This is but one of many Take Control titles! We have books that cover
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But it’s a better user experience and our authors earn more when you
buy directly from us. Just saying…
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the Kindle’s Mobipocket. All are DRM-free.

Copyright and Fine Print
Take Control of Your Productivity
ISBN: 978-1-947282-23-0

Copyright © 2020, Jeff Porten. All rights reserved.

alt concepts inc. 4142 Adams Ave. #103-619, San Diego CA 92116, USA

Why Take Control? We designed Take Control electronic books to help readers regain
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