How to Avoid Vacation Hell

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Be honest with my
team about why I need
Schedule 30 minutes
a vacation
planning time at
the beginning of each
workday
Delegate responsibilities
for ongoing tasks and
daily operational work Make a list of everything
that needs to be done
before I leave
Sort out reading list
for the poolside
Designate a deputy
Revisit my cash plan in case of emergency
and have a budget Set my away
meeting with finance message
officer

Unplug
Schedule a ‘catch up’
for when I return
 Making Vacations Possible
f you are routinely working late into
the evening and on weekends to
keep your business running, then
your business isn’t thriving. Your
late nights are long-term problems.
Entrepreneurial work takes brainpower—thinking
creatively about your business gets increasingly more
difficult when you’re tired. Your leadership style, or-
ganizational structure and time management skills
are holding you back.
Work can be productive and fun. It doesn’t have to be
all stress. Taking a step back to think about your vi-
sion for the future is a great way to work on strategic
problems in your business. Checking your phone and workday.
email to “get work done” suggests that you’re doing
the work your employees should be doing.
Writing out last-minute to-do lists for your team to
follow while you’re gone can mean many things:
micromanagement, failure to delegate, lack of train-
ing, or failure to recruit employees who understand
and have experience in their position. Writing out
procedures won’t get the job done. Before you go on
vacation, you need the right people trained and will-
ing to execute the tasks assigned to them. Putting a
system development and ongoing training program
in place will give you a chance to prioritize based on
your strategic agenda.
Leaving notes on what tasks need to be completed
suggests that you haven’t fully delegated respon-
sibility to your team. A weekly development meeting
with your managers should be structured enough
that you spend the time planning work. Adopting task
management software like Asana will help you man-
age employee meetings better and help organize the
Counting the cost of your absence indicates that
there is a serious structural problem in your business.
Simply put, your business can’t survive without you.
While a lot of small businesses tend to operate this
way, you don’t want to be like this forever. It’s time to
reconnect with your vision and ensure you’re build-
ing a team that follows your end-game goals.