Book Trainer

The Entrepreneur’s Guide to Keeping Your Sh*t Together by Dr. Sherry Walling

To enjoy the freedom of the entrepreneurial life, founders must take responsibility for their well-being through self-awareness, self-mastery, and self-care.

This is part of our Book Trainer series – training exercises for books. See the full collection here.

Big Idea

Being an entrepreneur is brutal on your mental health. To enjoy the freedom of the entrepreneurial life, founders must take responsibility for their well-being through self-awareness, self-mastery, and self-care.


Dr. Sherry Walling is a licensed clinical psychologist, co-host of the ZenFounder podcast, and the founder of ZenFounder LLC, a mental health consultancy that serves entrepreneurs and high performing professionals. Dr. Walling also has extensive experience supporting combat veterans, police officers, and families work through conflict, transition stress and crisis. As an entrepreneur married to an entrepreneur, she brings a unique professional and personal perspective on how to stay emotionally healthy as a founder.

My Story

I’ve found the most difficult part of self-employment to be dealing with failure, anxiety and loneliness. I’ve considered working with a therapist and was eager to read Dr. Walling’s thoughts on how entrepreneurs can best manage their mental and emotional health. This book outlines the common challenges founders face, and offers strategies to cope. Eventually I think I’ll need professional help – and psychological distance – to get a clearer picture of my mental health, thought patterns, and shadow. Nevertheless, I highly recommend this book as a starting point.

Exercise 1: Face Your Shadow

Dr. Walling makes the point that who we become as entrepreneurs is often based on our early life experiences:

“Your past shapes how you handle risk, disappointment, success, fear, relationships, and conflict… Even with all of your self-made, self-starting spirit and grit, the shadows of your past are shaping—and will continue to shape—the success of your business.”

She calls this facing your shadow, psychiatrist’s Carl Jung’s term for the dark-side of the human personality, the part of us that is largely unconscious, contains instinctive and irrational behaviors we don’t want to identify with, and is prone to bias and projection.

Our shadow experiences and pain are often the very things that make us stronger, better, and more creative. Unchecked, they can also lead to unhealthy behavior patterns and self-sabotage.

How does your childhood story and shadow affect the way you run your business?

Dr. Walling discusses four common entrepreneur types (the Golden Child, Loner, Pleaser and Survivor), their associated strengths and shadows, and how each can protect against potential blind spots.

Dr. Walling offers eight ideas to face your shadow. I include four below:

  1. Let memories be your teacher. Don’t avoid or ignore them, but learn from them.
  2. Whenever things aren’t going well, pause for a moment to consider self-fulfilling prophecy or self-sabotage. If one of those things is happening, take steps to overcome it.
  3. Contemplate your story. Who are you and where did you come from? And how did that story shape your values and your personality? 
  4. Learn to connect your past to your present. There is real power in saying, “This is where I come from, and this is who I am…”

This is about taking an honest look at where you come from, examining how it has shaped you and your business, and owning your story in an empowering way. 

As a “pleaser,” I am often blinded by my desire to impress and to be accepted. I grew up associating performance (in sports and school) with earning my parents’ love and attention. I’ve brought this childhood pattern into my relationships, often unknowingly. I still remember being surprised – almost shocked – that one girlfriend was crazy about me for me; I didn’t have to be or do anything special. Only after taking a hard look at my childhood was I been able to spot this unhealthy behavior.  

“If your past goes unchecked, it can be a script that you blindly live out, a factor that changes your business without you even realizing it. Likewise, if you carefully study your past—your upbringing, your natural tendencies, and your innate personality traits—you will become armed with a new arsenal of tools that will lead to greater success.”

Exercise 2: Break Free of Your Cognitive Distortions

“I spend a lot of time helping entrepreneurs develop the ability to notice patterns in their thoughts that have become unhelpful. In the psychological world, we call these ‘cognitive distortions’ or ‘maladaptive cognitions.’”

Dr. Walling’s five common cognitive distortions for entrepreneurs are filtering (focusing on the bad and incomplete), polarized thinking (thinking in all-or-nothing ways), over-generalization (coming to a broad conclusion based on a single piece of evidence), overestimating control (assuming full responsibility or blame for the state of one’s business), and thinking about the shoulds (absorbing goals from outside sources).

Dr. Walling’s five step process to “destinking your thinking,” which you can try, is:

  1. Observe. Pay more attention to your thoughts, especially when you’re stressed and overwhelmed. Pay special attention to words like “always,” “should,” “have to,” “must,” and “never” as well as to broad statements about yourself like, “I’m not good at this” or “I would never do that.”
  2. Start talking to yourself. Have a conversation with the thought pattern that is troubling you. Play attorney with your thoughts. What’s the evidence for and against this thought? Is there an alternative way of thinking about this? So what if the thought is true – what’s the worst that can happen?
  3. Look at yourself from a different perspective. Would you say the things you are thinking to a friend?
  4. Externalize your thoughts. Get your thoughts out so a trusted helper or peer can look at them objectively, and you can get an external perspective on your struggles.
  5. Reflect again. If negative thoughts still plague you, return to step one. Look for specific patterns of thinking that seem to underly the trouble you’re having.

It’s frightening to think that our thoughts and internal dialogue aren’t grounded in reality and have gone haywire. Nevertheless, not examining them could harm ourselves and our business. 

“We’re biased, especially about something we’re as deeply connected to as our business. Our thoughts still feel logical, but they’ve become skewed. They tell little white lies that have the power to be our undoing.”

Exercise 3: Use Problem-Based and Emotion-Based Coping to Manage Chronic Stress

Stress can be a good thing, but not when experienced over long periods of time. Unfortunately chronic stress is common for founders; there are always pressing deadlines, decisions and emergencies when running a company.

Chronic stress is related to every chronic health problem: heart disease, obesity, diabetes, cancer, and more.

Dr. Walling offers two ways to deal with stress: problem-focused coping and emotion-focused coping

Problem-focused coping recognizes that stress exists, and actively deals with it. The idea is to cut out as many stressors as possible. It’s also about changing your mindset: you can control how much stress you experience instead of being a defenseless victim.

  1. Take an honest look at your stress, and list stressors from all areas of your life.
  2. Problem-solve your stressors if they are changeable or avoidable. How you can eliminate or decrease this experience in your life?
  3. Make changes, collect data and adjust. Are your changes impacting your stress levels?

With emotion-focused coping, you don’t attack the problem (the stressor), but instead the emotions that come with it. Not all stressors are problem-solvable, but you can counterbalance stress with calm.

  1. Take time to notice physical symptoms of stress i.e. a tightening of the shoulders or feeling defensive.
  2. If you can’t problem-solve your stressor, try reframing it. For example, dealing with customer requests is not a burden but rather a great way to get insights about future products. 
  3. Counterbalance stress with calm by:
    1. Practicing activities that calm your emotions like yoga, running, reading, listening to podcasts, and meditating.
    2. Designating real-life “happy places” where you can go to allow your body and mind to fully refresh. This could be a park, lake or mountain near your home, a coffee shop, a corner of your apartment, a garden or a retreat spot. Make sure you have a physical place your body associates with rest and calm.
    3. Taking regular vacations and annual retreats. Research has shown that people who give their minds a break are better able to think creatively and to solve problems.

“Taking a vacation from your everyday life (and thus stress) is the best way to give yourself a reboot from all of the stress, while also giving you a better outlook on life and the motivation to achieve more.”

Powerful Quotes from The Entrepreneur’s Guide to Keeping Your Sh*t Together

“Being a founder is not a job; it is an identity. Your success depends in part on how you understand your own story and your role in the story of your business… You can repeat the story if it had a good outcome, or you have the power to try for a different ending. From the mission, culture, or efficiency of your company to the decisions that shape your family and your personal life, these stories are going to be the threads that carry you through difficult days and the inspiration that moves you toward success.”

“Ironically, one of the best ways to build personal connections is to have a healthy, strong relationship with your business.”

“Your business simply can’t carry the weight of who you are—it will never be your value or your purpose. Nor is it a good love outlet, because it just can’t love you back. Your start-up doesn’t have the shoulders to bear that weight, and it shouldn’t. So that misplaced emotional attachment has to go if you want to be healthy and strong for yourself, for your business, and for your family.”

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2 replies on “The Entrepreneur’s Guide to Keeping Your Sh*t Together by Dr. Sherry Walling”

Really great insights, I see so much of my own maladaptive coping mechanism in my life and how I show up in my identity as a change maker and entrepreneur. The step to pause and really observe and seek change is powerful. I’m so tempted to say, “let’s constellate that in a circle and untangle what we’ve carried from our ancestors!”

This line >> “the step to pause and really observe and seek change is powerful.” Amen.
Sadly hard to do despite all our technology and modern conveniences.

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