The Entrepreneur’s Guide to Keeping Your S**t Together

The Entrepreneur's Guide to Keeping Your S**t Together

Learn how to master your stress, dismiss your fears and rapidly accelerate your business growth.

The Entrepreneur's Guide to Keeping Your Sh*t Together

Learn how to stay sane, keep your s**t together, and ensure both you and your business thrive for years.

Running a business can ruin your health. It can ruin your relationships. It can ruin your life.
But only if you don’t equip yourself for the journey.

You run a business. And running a business is hard. The burden of responsibility, the weight of stress and the loneliness of running your business are a far cry from your friends who work salaried jobs. The stress and loneliness are real. Sometimes too real. The path of least resistance is to let the stress and isolation of starting, running and growing a business infiltrate most aspects of your life.

Trust us, we’ve seen it. Over and over we’ve watched our fellow entrepreneurs succumb to mental toll and chaos of running a business. We’ve also experienced it firsthand as we’ve launched and grown our own businesses.

Odds are good that you’ve been overwhelmed at some point.

Maybe you’ve tried talking to your spouse. That can work for a while… but your spouse is not your therapist. And placing them in this role inevitably leads to misunderstandings, fatigue and arguments.

Maybe you’ve talked to friends. But if they aren’t entrepreneurs, they likely don’t understand what you’re going through.

Or maybe you’ve read self help books only to find that books about stress management typically don’t take into account the unique experience of entrepreneurs. Or they’re ‘lifehacks’ written by a blogger with no formal training or credentials, offering advice based on anecdotes, not science.

This is why we wrote

The Entrepreneur's Guide to Keeping Your S**t Together: How to Run Your Business Without Letting it Run You.

This book is a focused, practical, researched guide written by people with the training, experience and expertise to speak directly to entrepreneurs...

Sherry is a clinical psychologist and an entrepreneur. Most people call her Dr. Walling or just Doc.

Rob is a serial entrepreneur who has launched, grown and sold multiple startups over the past 17 years.

At this point we’ve pretty much seen it all (well, maybe not everything - but we’ve seen a lot) through our conversations with thousands of entrepreneurs via:

We’ve seen the patterns that bring entrepreneurs down time and again. But we’ve also discovered the strategies, tactics, and techniques that have helped entrepreneurs like you triumph over the struggles of running a business. And that’s what’s in this book.

That’s why we sat down to write this book... to share the successful patterns we’ve observed from thousands of entrepreneurs: the strategies, tactics and techniques they use to triumph over the treacherous journey of running a business.

In others' words...


"A personal, generous and incredibly useful guide to staying sane and changing the world at the same time. Read it before you think you need it."

Seth Godin,


"Foundational for any entrepreneur looking to get their mindset right."

Dan Martell,
Chief Instigator @

Bridget Harris

"Sherry and Rob’s book is a gentle reminder that there is literally no point in building up a successful company and popular product, if you end up stressed, burnt out and heading towards some form of early grave.

The book offers a combination of practical strategies and strategic analysis on how founders can cope with this balance - and come out on top.

Thank you Sherry for giving me a long list of great advice and reminders on how I can stay healthy, happy, and run my business better."

Bridget Harris,
CEO and co-founder @

Who is this book for?


You might call yourself a founder, a CEO, a freelancer, an entrepreneur, or something else completely. The term isn’t important.

The common thread that weaves through each of these roles are the challenges you face, the mental struggles you must overcome, and the amount of stress and isolation created by your business.

Whether you run a startup, a software company, a medical practice, a law firm, a consulting business, or make your living as a freelance writer, designer or coder… this book is your guide to keeping your life and business together as you navigate the treacherous waters of entrepreneurship.

Who shouldn’t buy this book?

Wannapreneurs. People who aren’t serious about creating a successful business.

Haters. People who are looking to blame others for the things that happen in their lives.

Slackers. People who aren’t interested in the work it takes to improve themselves and their business.

Why do I need this book?

You want to invest in yourself (and consequently, your business).

You want to learn proven strategies, tactics and techniques to overcome the challenges that cause you heartburn and headaches.

You want to get off the treadmill of stress, anxiety and isolation that entrepreneurship brings.

You want to prevent burnout, depression, isolation, and the emergence of damaging coping strategies and self-sabotaging choices.

Every aspect of this book is a pairing of psychological expertise with decades of entrepreneurial experience. Here are just a few things you will take away from this book:

  • New ways to deal with the freedom, responsibility and existential fear that go along with being an entrepreneur
  • How to overcome the single biggest challenge every entrepreneur faces
  • How a single shift in mindset can make a lifelong difference in your success, happiness and fulfillment
  • Why knowing yourself and where you came from is crucial to your success
  • How to succeed as an entrepreneur no matter your personality type
  • How to keep stress from ruining your life and relationships
  • Identifying and dealing with depression, anxiety, burnout, ADHD and other common psychological burdens
  • How to get more things done – and faster – by dealing with procrastination, distraction and muddled priorities
  • Staying connected with your significant other, friends and key colleagues
  • How to deal with overwhelming success and (seemingly) massive failures
  • How to find personal calm in the midst of chaos
  • And much more...

What are other entrepreneurs saying about this book?


"Read this book as if your entrepreneurial dreams depend on it-  because they do. If you can't keep your sh*t (and that of your team) together you'll spiral out of control, make bad decisions and ultimately fail. I know what I'm talking about since I couldn't deal with the emotional challenges of entrepreneurship when I first arrived in Silicon Valley 10 years ago trying to pursue my dreams and build a successful business. I'm convinced that reading and applying the advice in this book back then would have prevented me from a 5 year startup journey that  ended in a soul crushing failure and put me in financial and emotional bankruptcy."

Steli Efti,


"This book covers the parts of starting and growing a business that aren’t shared often. The parts that most of us go through but don’t speak about. The ups and downs. The emotional roller coaster. Read this book whether you are already on your journey or just starting out. It’ll help you understand what you go through on a daily basis and how to manage it."

Hiten Shah,
Crazy Egg, KissMetrics, Quick Sprout, Product Habits, Draftsend & counting


"Entrepreneurship is mostly pain, with no one who truly understands to help us through it. Sherry is uniquely steeped in both entrepreneurship and clinical psychology, and wrote the book I wish I had read twenty years ago."

Jason Cohen,
WP Engine

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