It’s been more than one and half months since I posted my last review. It’s been quite a hard time for me these past few months. I started this bookstagram as a way to help deal with my mental health–which had been at rock bottom at the start of the year–and also as a self improvement habit I wanted to pick up. For the past month or so I think I’ve passed through a trough and I’m finally ready to get back to picking up where I left off. I tried going through two books in the past 1.5 months. One was a novel that really left me emotional every time I tried to process it. I read it three times and still couldn’t seem to write about it so I thought “OK I’ll read a business book which will be less emotionally straining”.
Then I happened to pick up this book because one of the co-authors, Rob, has a podcast (“Startups for the rest of us”) about bootstrapped startups that I have enjoyed following for years. This book’s primary author is Sherry, his wife, who is a trained psychologist. This book is a really clear no-nonsense guide for entrepreneurs for taking care of their mental health. I also had to read it three times to process everything because, little did I know when I picked it up, it was also emotionally intense.
The Wallings write in a very straightforward and personal way. They start by sharing their own personal journey of having to deal with juggling entrepreneurship and mental health: some years ago Sherry was finishing her PhD in psychology and preparing for an academic career, Rob was struggling to grow his email automation startup called Drip, and everything got so overwhelming that they almost decided to end their marriage.
From that point on, everything I read here deeply resonated with me, and I recommend this book to every entrepreneur.
They start out with reason that draw people to entrepreneurship, and for each reason provides a flip side that is unhealthy and dangerous if not handled well.
Before I proceed I have to talk a bit about my queasiness around the term “entrepreneur”. It took me about two years into starting my business before I felt like it was a label I could put on myself. I really balk at hustle culture, startup hype cycles, shameless self promotion, obsession with fame and fortune, the toxic love affair with capitalism, and everything else that signifies entrepreneurship in the popular imagination. It took me a while to convince myself that I’m doing what I do for reasons rooted in values that were wholesome, and because I prioritized independence and I love harnessing the creativity required to build something new, and if I’m honest, mostly because I’m too scatterbrained to hold down a day job.
The Wallings have their own list of values derived from their own lives and from interviews with hundreds of entrepreneurs: we do this because we value freedom, ingenuity, adventure and meaning. Freedom is paired with anxiety, ingenuity is paired with failure, adventure with instability, and meaning with isolation.
Freedom to plot the course of what you want to do comes with constant anxiety that you’re doing the wrong thing, and that even if you’re roughly on track that you’re not doing things the right way.
The ingenuity to come up with new solutions to problems comes with the risk that your idea/business/product–i.e. your baby–will die a horrible death in ways you didn’t foresee.
Your life is never dull because every new pivot, new project, new market is an adventure, but it comes with never having a fixed schedule or plan–you are always having to be comfortable amidst chaos.
Maybe you quit your day job because it was sucking the life out of you, and daydreamed about doing your own thing that is meaningful to you, and hopefully helps others find meaning too. But once you start on the quest to do your own thing, no one tells you what to aim for or what to do next, instead you have your whole team relying on YOU to lead and give them guidance.
“Being an entrepreneur is brutal on your mental health”, writes the authors, and backs it up with peer reviewed psychology research. For me it was comforting to read that out loud because it’s always a constant struggle to not feel guilty and convince myself this stuff is hard and other people struggle too.
The first half of the book digs into causes and types of mental health difficulties in entrepreneurs, ranging from how your childhood upbringing imprinted certain beliefs and internal scripts into your adulthood, to how personality traits like introversion and extroversion, and having a growth vs fixed mindset interacts with how you approach entrepreneurship. There’s a chapter on the ways negative thoughts that crop up like filtering feedback to just hear the criticisms, having an all or nothing mindset, overgeneralising from individual setbacks, and having arbitrary standards that you feel you should hit for no reason.
There are two really valuable chapters on mental illness and burnout respectively that really spoke to me. In the last few years I’ve lived through depression, anxiety, burnout and I’m also coming to realize that I’ve probably had undiagnosed ADHD since childhood and can’t wait to get a proper diagnosis. The authors write about how all these things are more prevalent in entrepreneurs than in the general population and go through a lot of ways of coping and getting professional help for these.
The other half of the book feels like a long coaching/pep talk that gives you tips and a toolbox to handle all the ups and downs. Setting and sticking to goals, keeping your energy and focus in check, dealing with inevitable crises within your business or when “life happens”, strategies to beat procrastination, the need to take stock, take breaks and the need to stay connected with your actual human loved ones and community you cherish–your business can become a significant other that has no ability to love you back–and finally it drives home an uncomfortable truth that “your first priority should be taking care of your company’s greatest resource: you.”
I’m sure this book will be one that I revisit once a year, because when I pick it up in a year I’ll be reminded of tips and coping strategies that would be relevant for whatever new struggles I’ll be dealing with.
If you have a business, or lead a team, or starting out on any kind of new project where parameters are unspecified and you have to chart your own course, I really recommend picking up this book.
Take care of yourselves, folks.