The Mental Health Booby Traps of Building a Startup

Before I started my company, I’d heard others talk about the connection between entrepreneurship and mental health. However, having been lauded for my toughness and optimism most of my life, I believed I’d be immune to mental health struggles many encounter on the startup journey.

I was not immune, and nobody is.

Every first-time founder who I opened up to about my own struggles while building a startup admitted they faced similar struggles of their own. Though of course, none of this gets talked about publicly. As Rand Fishkin, the founder of Moz, says in Mostly Human,

“As a CEO, you are asked by your investors, your employees, your friends and family to have this undefeatable nature. You are on top of the world. And the reality, of course, is entirely different...the startup odds are working against you all the time.”

I didn’t see the struggles coming until I found myself trapped in them. In that way, they’re a lot like booby traps. Now that I’m on the other side, I want to talk about them casually like the basic parts of the human experience that they are.

Here are the different mental health booby traps I ran into when building my startup at different times over three years. It took me a while to figure out how to navigate and cope with these effectively, and I still wouldn’t say that I’ve figured it all out.

Pressure of delivering on investor expectations

Raising money from investors changes your relationship with your business. You gain a fiduciary responsibility to try to get your investors a return. When things are going well, this isn’t an issue. If anything, it can bolster your confidence as your investors congratulate you on your milestones. However, when things are not going well, it can feel like you’re letting them down and you may feel embarrassed.

Supporting employees who are depending on you to support themselves

When you recruit employees to join your company, you’re selling them on a vision and a future where they’re able to advance themselves. When things are going well, this is still a constant responsibility, but when things aren’t going well, it may feel like you’re failing them (similarly to investors). Oh yeah, and there’s nothing worse than sweating out payroll.

Unclear sense of progress in your career compared to peers

As a startup founder, you come by your title (Founder/CEO) pretty quickly. But then what? You may see college friends get promotions, get raises, and begin living a more lucrative lifestyle. Meanwhile, your trajectory remains just as uncertain as your startup’s future. You are too locked in with your startup to think about your career path, and even trying to think about that can feel like you’re cheating.

Comparing yourself to others

Startups often depend on comparing themselves to other startups in order to get a sense of the right roadmap to take. While this can be a productive way to learn shortcuts, it can be hard to turn off. Comparing to others may sometimes make you feel better about yourself, but it inevitably leads to feeling like you’re not doing enough, not successful enough, or not {insert adjective} enough.

Over-leveraging your identity

I wrote about how I had over-leveraged my identity with Compass in a recent post. I explain how getting all of my self-worth from my startup wasn't just bad for me personally, but that it was bad for business as well. When things go well, it can be easy to feed your self-worth with your startup's accomplishments and slowly invest more and more of your identity in your startup as a result (because it gives you all of the self-worth you need). If you fall into that trap and things stop going so well, you find yourself in a difficult position where your sole source of self-worth dries up (not a great place to be). 

Drastic swings in outlook and multiple masks

Part of a CEO’s job is to pitch investors, selling customers, and inspire employees. Another part of a CEO’s job is to worry about the risks that could undermine the future.

As a result, it’s not uncommon for a CEO to say “This is going to work – I’m so sure of it” at to a stakeholder 3pm , “we’re fucked” to his/herself by 6pm, and “we’re going to make it” to an employee by 9pm. All three of these beliefs can be honest at the time they were stated.

The cognitive dissonance of holding these beliefs all in the same day can be mentally exhausting. Even worse, having such varying thoughts can make you feel dishonest or shameful even when you’re being honest and doing your best.  


I’ve only scratched the surface with the mental health booby traps that exist in the startup journey in this post (I can only talk about those that I encountered). The key is having the humility to admit that you’re not fully prepared to deal with all of them on your own. You’ll need the support of co-founders, mentors, family, and friends.

And, unless you’re a master at coping with stress and are a pretty wholesome human, you’ll probably need a therapist as well. After all, as a founder, your mental health is one of your startup’s most precious resources.

I started seeing a therapist after I’d fallen into many of these booby traps, and it helped me work my way out and avoid others. The next time I start a company, I’ll think my partnership with a therapist on a similar plane to a partnership with an advisor.

Mike Wilnerfundraising