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The Zen Founder Guide

to Founder Retreats

Sherry Walling, PhD

Contents
Introduction 4
Uncovering Opportunities and Possibilities 5
Shifting Perspective in Order to Bring Focus
Self-Evaluation and Setting Goals

Four Steps to Ensuring a Successful Retreat


Step 1: Allow Ample Time

Step 2: Choose a Relaxing Location 9


Step 3: Reset with Silence
Step 4: Unplug

10

Retreat Strategies and Activities


Strategy 1: Determine Highs and Lows
Strategy 2: Ask a Big Question

Other Retreat Takeaways

25

Take yourself seriously 27

11

15

Strategy 3: Do a Personal Assessment


Strategy 4: Map Out Your Goals

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24

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The Zen Founder Guide to


Founder Retreats

rue solitude is found in the wild places, where one is without


human obligation. Ones inner voices become audible. One
feels the attraction of ones most intimate sources. In consequence,
one responds more clearly to other lives. The more coherent one
becomes within oneself as a creature, the more fully one enters into
the communion of all creatures.
Wendell Berry

HE STARTUP LIFE is like drinking from a fire hose. Email


notifications, the buzz signaling a mention on Twitter, support
emails, contractor status calls, reviewing code, recording screencasts, producing blog posts and podcasts ... the pace is frenetic. There
is always one more thing that needs to be done. And it works well for
many of the intense, highly motivated people who are drawn to the
entrepreneurial life.
Tackling the task list day after day means there is limited time and
space to consider the big-picture direction of your business and
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The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

your life. The urgency of shipping overshadows the non-urgent,


seemingly esoteric questions:
Am I happy?
How can I improve my relationships?
How do I want to grow over the next five years?
Is the current structure of my business working?
What do I want to accomplish in my work?
For many, there is too much noise to let the mind explore big
questions.
Yet, there is real danger in failing to give space to existential questions. Business partnerships, marriages, and products fail because
people neglect to periodically inspect the basic structure of what
theyve built, of what they want.
We are not static beings. A subtle drift away from earlier goals,
values, and assumptions can become a voluminous canyon if the
shift goes unnoticed for too long.
This is why a Founders Retreat can be such a critical piece of not
only your mental health, but your long-term business health.

Uncovering Opportunities and


Possibilities
Retreats offer the opportunity to do an internal check-in: to notice
change, to assess whether the default settings are still optimal.
Its possible that under the standard thoughts that permeate dayto-day life, there are some truly creative ideas that are waiting for
space to be birthed. What might be lurking in the depths when we
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The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

give ourselves the freedom to ignore the nuts-and-bolts and imagine our lives sideways and upside-down? What is possible when we
are handed a blank mental canvas?
Stagnation is a dangerous enemy to the founder whose livelihood is
based on novel solutions to everyday problems.

Shifting Perspective in Order to Bring


Focus
A retreat is a shift in perspective. It is a time to step back and see the
proverbial forest, not just the trees. It is an invitation to call a brief
truce with the onslaught of daily tasks and demands so you can
pause and gather yourself. It is a time to ask deeper questionsto
mull, to ponder, to create, to dream. A retreat is a time to make
careful choices about the future of your business and your life.
Make no mistake: A retreat is not a vacation. It is not time to down
margaritas and sign up for a hula contest. It is focused. Alert.
Solitary. Serious.
It is not a time out. It is a time in.
A retreat can be the activity around which you build your entire
year. One strategy for a retreat is to establish a set of clear priorities
or goals to be pursued in six months, a year, or whatever timeframe
you need to work with.
Setting aside time to bring focus to your professional activities can
help direct your energies and serve as a litmus test for when to say no
to opportunities that present themselves. Without predetermining
the focus of a year or six-month period, it can be easy to spend a lot
of time churning through the pros and cons of every opportunity.
A retreat saves this energy. It makes no easier and yes clearer.
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The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

Self-Evaluation and Setting Goals


Retreats also allow for the development of personal goals. The questions center not only on what you are doing, but why. Retreats can
be a time to engage in careful self-evaluationto really look and
see if you are good with what is happening in your life.
Are you taking enough risks?
Are you learning?
Are you growing in the ways that are important to you?
Are there inconsistencies between who you say you want to be
and how you are living your life?
Are you really pressing into the growth of your product?
Could you dream bigger?
If you are a parent or are in a relationship, retreats are also a time
to consider the needs of others in your life. Are you interacting
with your kids in the ways you want to? Are you and your spouse
communicating well? Are you supporting each other?
If done well, retreats can become an integral part of the success of
both your business and your life.

Four Steps to Ensuring a


Successful Retreat

HERE ARE A number of strategies you can use to help set


yourself up for retreat success:

Step 1: Allow Ample Time


Go for at least two nights. It takes 8-10 hours to decompress and
switch into retreat mode. Twenty-four hours is too shortit means
you have to rush around and force the work to get done.
It is best to spend the first afternoon on the beach, in the forest, in
front of a fireplace, in a park, in a coffee shop someplace that is
relaxing and not too stimulating. Let this be a time to observe and
unwind.
Dont be worried if you spend hours decompressing. It takes time
for your brain and your body to shift from the frenetic pace theyve
been working. Its okay to sit in a coffee shop staring at a notebook
for hours. Sipping chai. Thinking. Watching people. Just letting the
day-to-day drift out of your head

The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

Step 2: Choose a Relaxing Location


Choose a location that is comfortable and calm. Steer away from
urban environments with a lot of stimulation. Mountains, beach,
or desert are the optimal settings for most people. Fresh air and
sweeping landscapes clear the mind and allow for a new rhythm.
There is a reason monks and others pursuing prayer or religious
enlightenment have traditionally sought their epiphanies in wild
places.

Step 3: Reset with Silence


Consider beginning your retreat with silence. Take a retreat a few
hours from your house. Unlike day-to-day drives, dont listen to
podcasts or audiobooks or even music during this drive. Its a nice
way to start decompressing and just think. It is a type of meditation. Notice what enters your mind, observe the thoughts, and then
let them move on.
A few hours of silence can give you a nice snapshot of what youre
worried about and how youre spending your mental energy. Pay
careful attention to the thoughts that most earnestly try to intrude
on the quiet.
Silence can be uncomfortable. It can feel like wasted time. It can
feel lonely, or boring. Silence is part of the hard work of retreats
(yes, they are hard work).
Letting there be silence allows us to shift out of the rapid pace of
information consumption and response that is the daily reality for
most of us. Silence is a different kind of mental discipline that forces
internal focus and counters external distraction.

The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

Step 4: Unplug
Try to leave the laptop at home. Really try to not check email at all
during this time. The further away you can get from any kind of
day-to-day concerns, the more your mind is free to wander.
Turn your notifications off. Because so much work time is spent in
front of a screen, it is best to use a pen and paper to record notes
and ideas. If retreats become a regular part of your life, you may
have a notebook just for retreats. Another option is to use a role of
butcher paper and markers to record your thoughts.
The space, the techniques, the way you structure your time, is all
with the purpose of interrupting your default patterns. The steps
above will give you a good starting place for creating a retreat that
will help you do this.

Retreat Strategies and


Activities

ETREATS ARE HIGHLY individualizedthere is no one


right way to spend your time while you are on one.

Each year may be different. Some years, you may be in the midst of
a crisis. Your retreat may be an intense gasp for air in the midst of
drowning. Other years, your retreat may be a pleasant time to rest,
write poetry, and re-up on your existing goals. There is no perfect
plan that will work for everyone, every time.
Below are a few activities that are commonly used during retreats.
You can build a retreat around one activity, or combine a few different activities based on your needs.

Strategy 1: Determine Highs and Lows


One of the most powerful retreat strategies is to take a careful
inventory of how your life is working by examining the highs and
lows of the past year. The highs and lows can cover big events as
well as the smaller (dis)satisfactions of daily life.

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To contemplate your highs, ask:


When have I felt most alive?
What energized me this year?
When have I felt happy, content, or joyful?
When have I been the best version of myself?
What am I most proud of?
When considering your lows, ask:
What were the low points of the past year?
What events or tasks seemed to suck the life out of me?
In what situations am I most irritable, impatient, or angry?
When did I make an unwise decision or really lose my cool?
What contributed to those experiences?
What do I regret? What am I embarrassed of?
Think about the highs and lows in the different facets of your life
professionally, as an individual, as a wife/husband/partner, or as a
parent.
Reflecting back gives you the big picture about what parts of your
life are working well and what parts are not. The recent past is the
best source of data to inform the adjustments you might need to
make.
When you look at your list of highs, ask yourself:
How can these events or experiences be a greater part of my
life in the year ahead?

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How can I spend more time and energy doing these kinds of
activities?
What made this experience such a highlight, and is it possible
to replicate this in other areas of my life?
Ask yourself how you can maximize the parts of life that are working well.
For example, if one of your highs was watching your intern rock a
new marketing campaign, consider whether teaching and mentoring should be a larger part of your work life during the next year.
When it comes to lows, it is important to consider three
questions:
Is this low a changeable part of my life?
If this low is not changeable, how can I change my response
so that it is not such a negative emotional experience?
What am I learning from this?
If there is a changeable event or situation that made your low list,
think about the changes that need to be made so this experience
does not show up on your low list again.
An example from my life:
Two years in a row, I saw the same lows show up in my retreat reflections: faculty meetings, grading, high email volume about unimportant issues, boring administrative responsibilities I couldnt ignore
the fact that I was really unhappy at my teaching job. Even though
Id spent years preparing to be a professor, my retreat helped me to
clearly see that the job wasnt fitting for me. Too many of my lows
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The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

were non-negotiable parts of the job. During my retreat I made the


decision to resign. The decision was absolutely the right move for me.
If there are lows on your list that are not changeable, consider how
you might make the stressor less emotionally difficult.
For example, if you are struggling with a chronic illness that you
cannot change, you might ask yourself: What could be done to
make it less of a low? A stronger community of support? A treatment review by a different physician? Additional medication? Yoga?
A diet change? More humor? If you cant change the challenge, perhaps you can change the way you approach it.
It is also important to consider what youve learned from your lows.
Do you know more about hiring and managing now that youve
had to fire a bad employee? Do you know more about product-market fit now that your ad campaign failed miserably?
The goal of the High-Low strategy isnt to make a life comprised of
unicorns and rainbows. Lows will always be part of life.
How the High-Low Strategy Can Help You
Asking these questions is powerfulthe way you respond can lead
to changes in the direction of your career, the way you structure
your day-to-day life, where you live, or who you choose to spend
your time with.
Take seriously how you feel about your life and be willing to adjust
or eliminate shoulds and default expectations so that you are
maximizing the moments in which you are fully engaged and
alive.
The way you address future-oriented questions should be based on
what you came up with during your reflections on your recent past.
Collect data based on what is really happening in your life. Your
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The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

goals should be informed by your sweet spots, the areas where you
are already thriving.
Remember: You have to look back in order to look forward.

Strategy 2: Ask a Big Question


Depending on your situation, you may take a retreat to ask yourself
a specific question about your future:
Should I leave my consulting job?
Do I need to take on (or break up with) a business partner?
Is my marriage salvageable?
Should I sell my app and start over?
These are big questions that require slow, careful consideration.
Consider engaging these questions with a mixture of writing,
walking, napping, and intentional distraction.
Begin by retracing your steps and reflecting on how this question
came to be important to you. What signaled the need for this potential change? Reflect back to gather some data.
Notice the emotions that led up to this decision. Be suspicious of
feelings like vengeance, shame, anger, inferiority, or fear. These
emotions may complicate your ability to make a sound decision.
If you notice that your motives might be shaded by these kinds
of feelings, stop. Put your decision on hold and instead focus your
time and energy on a plan to work through the situation causing
these feelings.
Dont make decisionsdont even think through big decisions
when you are:
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The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

Hungry
Angry
Lonely
Tired (HALT)
or when you are
Vengeful
Inferior
Ashamed
Also, pause to make sure this question is really about the well-being
of your life (as opposed to the desire to rearrange the life of someone else without their consent). Recheck your assumptions before
moving forward.
Assuming none of the aforementioned complications apply,
consider:
What makes it difficult to ask this question?
Jot down your anxieties. Attempt to suspend anxiety for a few
hours. Allow yourself to think through this question without the
emotional burden. Make it hypothetical for an afternoon.
Why are you asking this question?
Go slow. Start writing, take a walk, and write more. Write your
responses and review them a few hours later. Take the time that
you need.

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The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

What are your options?


Map out the potential courses of action. Again, take your time.
Force yourself to think beyond the typical two choices. Think outside the box. Get creative.
Force yourself to come up with ten alternatives. Ideas 1-3 are your
default answers, ideas 4-7 will probably be ridiculous and unhelpful, ideas 8-10 may be brilliant.
Write down some bad ideas. Press through the defaults to make
sure your way of thinking about this question is not overly narrow.
Take a break. Go for a run, a swim, or a bike ride. Eat a meal.
What are the pros and cons of the viable options?
Return to your list of possibilities. Toss out the infeasible and
terrible ideas. Begin to assess the pros and cons of the realistic
contenders. Write down your thoughts so you can retrace your
steps later.
Consider the pros and cons at both a professional and personal level.
Be honest. No one else has to see this document. Get your thoughts
on paper where you can interact with them. Consider your current
emotional state and notice your feelings about the potential courses
of action.
You might develop a table that looks something like this one, which
is based on the question of whether or not to bring on a technical
cofounder.
Take another break. Go to sleep. Watch a movie. Turn the music up.
Read about something totally unrelated.

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The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

Yes, seek out a technical


cofounder

Offer small equity


to current mid-level
developer

Stay solo with technical


contractors

Personal Pros:

Personal
Cons:

Personal Pros:

Personal
Cons:

Personal Pros:

Personal
Cons:

Business Pros:

Business
Cons:

Business Pros:

Business
Cons:

Business Pros:

Business
Cons:

Fears associated with this


option:

Fears associated with this


option:

Fears associated with this


option:

Feelings associated with this


option:

Feelings associated with this


option:

Feelings associated with this


option:

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The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

What does your gut tell you?


After a long break or a good nights sleep, ask your question again.
Dont review your notes, just ask from a fresh perspective, a fresh
mindset. Do you have a different leaning now? What does your gut
tell you?
What does the path look like?
Return to your work from the previous day. If you have a tentative
decision in mind, begin to map out what it will look like to pursue
that course of action. Be specificinclude plausible benchmarks
and timelines. Break down the steps. Consider who will be affected
by your decision. Think through implementation.
This process may be the bulk of your retreat, especially if youve
come to your question with a pretty strong sense of your course of
action.
If your sense of direction is solid and youve mapped out your steps,
begin to set your decision in motion. Make plans to meet with your
co-founder, advisor, mastermind, or therapist if youd like a final
double-check. Begin to make other plans for how to start implementing your decision as soon as you return.
After careful thought and clear-headed reflection, trust yourself.
Trust that you are making the best decision you can with the information that is available to you. Dont be afraid to commit. Dont be
afraid to lean hard toward a goal. Let yourself embrace the risk and
decide to go for it.
If Your Course is Still Unclear
If your course of action is still uncleareven after hours of careful
thought and attempts at problem solvingit may be that the lack of
clear direction is in itself some kind of answer.
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Uncertainty may stop you from going in the wrong direction. Maybe
it isnt time to decide. Maybe something is blocking a decision.
Consider spending some time thinking about why the decision is
unclear at this point. Make some notes about what information or
events will make the decision more feasible. Consider consulting
a therapist, coach, or mastermind group to help you assess why
youre stuck and what your options might be.
Although it is important to act on your retreat insights, there is no
point in forcing a course of action simply because you want to have
clear takeaways from your retreat weekend.
Deciding to wait on a decision is an important decision in itself.

Strategy 3: Do a Personal Assessment


Retreats are a time to shift away from the tasks of life and ask big
questions. No questions are bigger than the questions of self:
Who am I?
What is important to me?
Though the foundation may be well established for most adults, it
is important to pay attention to the shifts that happen in our values
and identity as we gain experience, encounter difficulty, and grow
as people. Values change with the arrival of children, the failure of
a business, or a break-up. We change.
Retreats are a perfect time to revisit questions of identity, personal
strengths, and values. These questions are particularly helpful if
you are in the midst of a shift in your business or your personal
life, but are not ready to tackle a specific decision during your
retreat.
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Reconnecting with your own sense of personal priorities can help


you create guidelines to inform later decisions. Self-knowledge is a
powerful tool. It keeps you from wasting time on things that dont
matter, or youre not good at.
Some questions to guide your reflections:
What am I most proud of right now?
How have I changed in the past year?
What sets me apart from my peers?
Who do I most admire? What about them do I admire?
Am I using my time wisely?
What activities are most important to me?
What am I unwilling to live without?
How is my life different than I thought it would be at this
phase of my life?
Another helpful strategy is to use a formal personal assessment
tool. There are several well-respected instruments that are available
online, as listed in the table below:

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Instrument
Values in Action (VIA) Survey
www.viacharacter.org

Summary
Based on 25 values which are ranked
for each individual
Applicable to personal as well as
professional life

Strengths Finder 2.0


strengths.gallup.com

How the World Sees You


HowtheWorldSeesYou.com

Myers-Briggs Type Indicator


HumanMetrics.com

120 Questions
Identifies your top 5 strengths
Focused on professional life

49 personality types
Based on others perceptions of you
Emphasis on professional life
Classic 16 personalities based on Jungs
theory (ENFT, ISTJ, etc.)

Cost
Free initial
survey;
detailed
reports range
from $24 to
$40
$15 book
comes with
survey access
code; extensive
report
$18 book
comes with
survey access
code
Free

Helpful for personal as well as


professional life
64 questions

For any assessment measure you choose, take the assessment, read
the accompanying materials, and spend time engaging your results.
How to Engage Your Assessment Results
Look at your results. Are there any surprises? Does the assessment
match the way you view yourself? Note any discrepancies.
What does the assessment indicate about your unique strengths?
Based on the accompanying interpretive materials, what activities
seem to be the best fit for the kind of person you are? How can you
better highlight your strengths in your daily life? In your relationships? In your business?
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It is important to have a solid sense of your own strengths and values


before you begin to map out goals. According to the folks that wrote
and conduct research with the VIA Survey, people who set goals
that are consistent with their signature strengths tend to make
more progress and report higher overall well-being.
While there is a time and place to work toward strengthening our
relative weaknesses, the bulk of our time and energy should flow
out of who we innately are. Personal assessment can help confirm
what you already know about yourself. It can also hint toward
strengths that you may be less aware of that have developed with
age or over time.
Look again at your results. You may select one value from your
assessment and make it a theme for the year. For example, if your
VIA survey or Strengths Finder assessment indicates that you are
someone who values Love of Learning, you may spend part of
your retreat time outlining a few things you would like to learn over
the course of the coming year. Perhaps you decide to work with a
chess coach, read a series of books about neuroscience, re-sharpen
your coding skills Your values guide your time and energy.
Like the High-Low exercise, personal assessment helps you look
toward the future from the inside out. You choose the parts of you
that you want to feed.
A human being has so many skins inside, covering the depths of the
heart. We know so many things, but we dont know ourselves! Why,
thirty or forty skins or hides, as thick and hard as an oxs or bears,
cover the soul. Go into your own ground and learn to know yourself
there.
Meister Eckhart

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The Zen Founder Guide to Founder Retreats Sherry Walling, PhD

Strategy 4: Map Out Your Goals


Most retreats end with some version of goal setting. Goal setting
involves spending intensive time mapping out the steps needed to
accomplish specific goals.
The fewer goals are better.
The number of serious goals youre working on at once should not
outnumber the fingers on one hand. The more focus you give to each
goal, the greater your chances of success. Select between one and
three goals for your business, and between one and three goals for
your personal life.
You may set a goal to increase your revenue by 5x in the next year
alongside a goal to tackle a Tchaikovsky concerto on the piano. You
may set a goal of decreasing churn by 20% and set a goal to help
develop a robotics program at your kids middle school.
Some goals will be more intense than others.
There are many resources available to help you stay on track while
mapping your goals. One quick, helpful acronym from mindtools.
com is SMART:
Specific
Measurable
Attainable
Relevant
Time-bound or Trackable
Make your goals very specific. Spend time fleshing out the steps
for getting there. Make a timeline with benchmarks on the way.
Be specific about the steps you will need to take to get started, to
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grind away, and to complete your goal. Be clear about what success
means, and make a plan to celebrate accomplishing the steps along
the way.
Here is an example of how you might outline steps toward a goal:
Goal: Write growth hacking ebook
Step 1: Protect writing time in schedule
Step 2: Draft outline and review with mastermind
Step 3: Schedule writing retreat in January to finalize outline
and begin chapter 1
Step 4: One chapter due on the last day of the month, January
to July. Plan a dinner date to celebrate each completed chapter
Step 5: August 1send draft to mastermind for review, revise
Step 6: September 1send draft to professional editor
Step 7: October 1book launch. Focus on marketing.
Step 8: Throw small party with friends or go away for a weekend with a girlfriend.
Your steps could be even more detailed than the ones listed above.
Your timelines may vary dramatically. The point is that youve
thought it through and set some benchmarks you are accountable
to.

Other Retreat Takeaways


Your goals dont have to be the only takeaways from your retreat.
Goals are the actionable, observable steps that youre taking toward
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a change in your life. But if youre not ready to commit to a decision, dont make it a goal.
You may also come away from your retreat with general directions
or intentions for change: spending more time playing with your
kids, consuming less alcohol, spending less time on a negative
forum, exploring the possibility of acquiring a new app.
Identifying general ways youd like to grow is important. Its helpful
to list a few directions for change alongside (or instead of) intense,
actionable goals.
You may leave a retreat with 3 specific goals and 3 directions for
change. Thats time well spent.

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Take yourself seriously

EVE GIVEN YOU four detailed strategies for retreat


activities. As we mentioned above, a retreat is highly personal. You may combine two or three of these activities, or focus
on just one.
What you do during your retreat time should be based on whats
going on in your life. It is helpful to spend some time preparing
for your retreat and taking an inventory of what your needs are.
Mapping out a simple plan can help you optimize your time.
If you are in the midst of a big decision, spend most of your time
asking the big question. If your business is ramping up and you
are preparing for big changes, spend most of your time on goal
setting.
If you are not in the midst of a big shift, spend most of your time on
the highs and lows, or a personal assessment. These two activities
are also helpful if you are feeling stuck or discouraged.
If you set a goal or make a decision during your retreat time, act on
it. This may mean leaving a job, retiring an app, beginning a new
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relationship, or selling your house. Trust your decisions when they


are based on clear-headed, careful reflection. Commit.
Also, dont forget to rest.
Doing your retreat time should not come at the expense of quiet,
sleep, exercise, and time for uncharted, blank-slate thinking. Dont
be rigid with your retreat plans.
The big issue is that you are solidly in possession of your life. You
are not a rat running a maze for a crumb of food. You are engaging
in your life with your eyes open and your mind, heart, and wits
about you. Retreats are where you recalibrate and tune in to your
own instincts, emotions, and wisdom.
Many people are longing for permission to step away, longing for
space and time to think. Give yourself permission. For the good of
your business, your family, and your own well-being.
Give yourself permission to retreat.
Who looks outside, dreams; who looks inside, awakes.
Carl Jung

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During the past year

In the coming year

When did I feel most


happy and content?

What were the low


What would I like
points of the past year? to see happen in
my business? In my
relationships?

Goal #1: Steps to take to


achieve this goal (include
timelines if possible)

What am I proud of?


Consider a range of
possibilities: business
accomplishments, acts
of kindness, enduring
something difficult,
etc.

Which experiences
caused the most
anxiety, anger, or
frustration?

What life-sucking
aspects of my life do I
need to minimize or
eliminate?

Goal #2: Steps to take to


achieve this goal (include
timelines if possible)

What moments or
experiences reflected the best of me?
Reflected what I want
my life to look like?

What actions or decisions do I most regret?

How would I like to


Goal #3: Steps to take to
grow as a person? What achieve this goal (include
would I like to learn?
timelines if possible)
What risks would I like
to take?

28

Das könnte Ihnen auch gefallen