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TAKE CONTROL OF
YOUR
PRODUCTIVITY
by JEFF PORTEN
$14.99
Table of Contents
Read Me First ............................................................... 5
Introduction ................................................................ 7
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Run Both Systems Side by Side (Temporarily) ..................... 86
Do Things ....................................................................... 93
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Consider Everything ................................................ 157
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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.
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.
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
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and access any future updates. However, if you bought this ebook
elsewhere, you can add it to your account manually; see Ebook Extras.
Version 1.1 of this book updates the text to reflect changes in both
software and approaches by the author. The most significant changes
were:
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Introduction
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 can feel external pressures and the metaphorical heat increas-
ing, and you have to proactively increase your skills to match.
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 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
porch.
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.
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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.
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.
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• 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).
• 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.
• It’s natural to have times when things get out of whack; when that
happens, Fail Successfully.
• 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
Book?
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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
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
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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.
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).
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
plan.
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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:
• 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.
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
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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.
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.
• 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.
Obviously, that’s chaotic, but there are other reasons why it’s a bad
approach:
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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.”)
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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.
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these are actually Whenever tasks that aren’t due, then Flag Fewer
Whenever Tasks so that they match your available time.
• 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.
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
time.
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better track record until you’ve established a better track record—
which is a common result of better planning.
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.
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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.
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.”
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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-
fort.
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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.
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.
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Roles
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.
Goals
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.
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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.
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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.
Journeys
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.
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.
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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.
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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
likely.
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.
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
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because once they’re written down (and you refer back to your list),
they’re unlikely to automatically play second fiddle to lesser tasks.
• 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.
• 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?
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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.
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
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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.
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.
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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.
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For now, decide which of the following approaches better suits your
style and preferences:
• 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.
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.”
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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
time.
Your system can handle all of the above, but you should have high
conceptual walls between them. If you put too much Commitment
33
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.
• 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 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.
34
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.
• 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.
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.
• 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.
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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.
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
pen.
‣ 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,
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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.
38
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.
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.
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-
39
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.
40
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.
41
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
straight.
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.
42
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.
43
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.
44
• 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.
• 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
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
45
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
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).
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).
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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-
sary.
Events
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.
47
All events fall into one of three categories:
• 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.
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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.
When your calendar is filled with a mix of hard, firm, and soft events,
with no distinctions made between them, there are three bad
outcomes:
• 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.
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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.
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.
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
50
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
appointment.
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
51
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.
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
52
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?
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-
53
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
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.
54
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.
55
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.
Contexts
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
56
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
leisure.
57
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.
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.
58
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.
1. This isn’t a step, but I’m listing it first because it’s something you
keep in mind from the start.
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.
59
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
tomorrow.
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.
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.
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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-
thought.
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).
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important information about what to prioritize when choosing better
tools.
These are the categories to consider when you’re doing this review:
There are three ways to move your tasks into your task app:
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cloud services you’re already using; it’s annoying if most of your
stuff is in Google Drive, but your app insists on Dropbox.
“too expensive.” Of course that’s true if you don’t have the money,
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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.
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.
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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:
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
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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.
• 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
options.
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• 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.)
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.
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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.
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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
apps.
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
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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.
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Figure 10: One of the Trello “Inspiration” boards that provide
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,
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but as Trello is more visually oriented than outliners, it’s less than
optimal.
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.
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
structure.
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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.
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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.”
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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.
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.
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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.
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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.
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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.
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
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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.
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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.
• 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.
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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.
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
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they’re shiny new toys, while others enjoy the process about as much
as blisters while they’re breaking in new shoes.
• 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.
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.
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• 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.
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.
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.
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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.
place to put it where you’ll see it later. This can be a note in a task
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
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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.
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.
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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.
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.
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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.
Creating granular and specific tasks is also a habit you can start now:
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.)
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.
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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.
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
migration.
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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.
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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.
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.
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).
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Figure 15: The quick capture feature of OmniFocus.
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.
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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:
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.
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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.
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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.
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.
‣ 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.
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them, had any basis in reality compared to what you’re actually
getting done.
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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.
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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.
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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.
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
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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 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.
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.
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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 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:
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:
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that small thing says you’re neglecting your home management, which
in turn means your work-life balance is entirely out of whack.
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.
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.
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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.
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.
• 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.
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• 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.
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.
Note: For tips on how to reduce the pain of recurring due tasks, see
Force Your Recurring Tasks to Be Humane.
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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.
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
most.
1. Start with the project and the deadline date. Just know what they
are; don’t put them anywhere just yet.
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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
project.
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.)
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.
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.)
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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.
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.
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
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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.)
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
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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.
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
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works well as a time block and what doesn’t, you can use that informa-
tion for future decisions about similar tasks.
• Revenue: Only the things I get paid for. Easy to identify, but
without the context, they can be the last things I do.
Note: However, note the decisions you made when you started.
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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.
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.
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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.)
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.
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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.
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.
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).
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Figure 16: The beginning of a yak list, with the “official” task in
bold, preceded by the steps I took away from it.
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).
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Figure 17: A yak list that spawned a baby yak, with indicators
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.
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.
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.
‣ 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.
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‣ 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
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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.
• 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.
• 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-
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ication to keep going off periodically the rest of the day, asking if it’s
time for your third.
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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
elsewhere.
Projects
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:
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‣ 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.
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• 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.
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
Everything.
Individual Tasks
• 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.
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• 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.
it, the more your task app will give you a manageable Due list.
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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)
accordingly.
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
• 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.
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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
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.
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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.
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:
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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.
• 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.
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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.
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
respond.
• 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
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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.”
‣ 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
instead.
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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.)
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.
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.
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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.
• 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.
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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
about.
• 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.
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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-
sions?
• 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.
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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
exceptions:
✦ 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.
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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.
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.)
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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.
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
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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.
• 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
place.
• 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
here.
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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.
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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.
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 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
future-you.
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.
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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.
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
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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
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them recurring tasks, if you need regular encouragement: “Did you
take a walk around the block this afternoon?”)
• 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.
“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.
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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.
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
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reasonably fresh or obviously moldy. You were more organized
before you got off track. That will make this time much faster.
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.
‣ 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
expected.
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.
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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.
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.
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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.
• 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.”
• 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.
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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.
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
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better (or just made difficult things bearable), maybe you adapt them
to better times and keep them.
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
yourself.
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.
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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
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.
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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
decisions.
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.
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.
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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.
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.)
Exercise
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.
Caffeine
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
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“health is everything” crowd, who don’t much care which “chemical”
you’re putting into your body—they’re all bad.
Note: I take Ritalin for ADHD, and speaking only for myself, energy
Diet
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.
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Sleep
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.
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.
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,
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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.
your coworkers used to your being away from your desk for 30
minutes.
done when I stay 30 minutes later and take a nap at 3 P.M.,” then
155
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.
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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-
ly.
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.
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
occurs.
There is one instruction on what not to do, and that’s make any large
decisions about your new system.
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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.
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.
If you don’t need that kind of wholesale revision, don’t revise at all.
Tweak.
158
After Three Months
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.
Six Months or So
159
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?
A Year or Two
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
160
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
choices.
161
Are You Rereading This
Book?
There are three categories of people reading these words. Each of you
get different instructions.
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!
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.
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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.
read, with capsule summaries to let you know how applicable they
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.)
163
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.
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.
164
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.
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.
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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.
Ebook Extras
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If you bought this ebook from the Take Control website, it has been
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About the Author
Acknowledgments
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.
167
About the Publisher
Credits
• Editor and Publisher: Joe Kissell
• Cover design: Sam Schick of Neversink
• Logo design: Geoff Allen of FUN is OK
168
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Take Control of Your Productivity
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