Let's Talk About Founder Depression

Being a founder is supposed to be hard. It’s supposed to require hard work, but how much? Did you do enough today? Was six, eight, twelve, hours enough? Is your company failing because you didn’t respond to that email instantly like you’re supposed to?

A founder reads that every email should be responded to instantly, or that you should be interviewing fifty people a day. They aren’t. Maybe they only worked eight hours yesterday, or they felt a little down and didn’t manage to get much done at all.

At the same time, their company is not doing perfectly (no company is). They aren’t acquiring quite enough customers, or their product isn’t working as well as it should. Suddenly that failure is their fault, and their inability to get things done means they are failing at being a founder. Every other company is ran by someone who wakes up at 5 am ready to go, and they don’t. They can’t make this work, and soon everyone will know.

Covering up their depression and apathy becomes its own project, because to be a founder you must at least project the right kind of energy. Quickly a cycle develops, where depression leads to missed work opportunities, and those missed opportunities create crippling guilt which feeds the depression. Every conversation becomes a farce, because the one thing which can never be revealed to employees and investors is apathy. Monday morning becomes a hell of not-working and not-relaxing, as the guilt ruins even the quiet moments. Eventually escaping the pain of failure becomes its own pursuit, the founder begins to fill in the dark times with avoidant behaviors which could be anything from TV to drugs.

Maybe the founder is replaced, or the company fails, OR the founder learns-painfully-how to manage their own emotions and become the effective contributor they can be. I am going to help you do just that.

Breaking the Guilt Cycle

Yesterday you didn’t get as much done as you hoped for. Maybe you stopped work at 3 and played some games or spent time with your family. You have failed to meet your own expectations. You now have a choice:

• Feel guilt and shame
• Not feel guilt and shame

This sounds trivial and trite, but it’s everything. If you decide to feel shame about your failure, you will get increasingly down on your ability as a founder, and your value to your organization. You will eventually exhibit this depression to your team as anything from exhaustion to apathy to anger. Your attempts to hide your true feelings will distance you from that team. Guilt will gradually break down your confidence and the feeling that you are meaningfully contributing. Eventually getting out of bed will be hard, workdays will get shorter and shorter, and your contributions will dwindle even further.

You will be in a dangerous spiral where every failure to put in the work creates negative feelings, and the darkness of the negative feelings cripples your motivation to put in the work. Eventually the negative feelings might become so strong that you will begin to try to avoid them through drinking or other distractions.

If we take another tack however, we will get different results. Let’s return to that day when you stopped work early, and reframe it. What if, instead of guilt, you say “I guess I needed a break today.” If you refuse to feel shame for your actions, the cycle can never begin, and you will start tomorrow anew.

But let’s say you do something really atrocious. Perhaps you spend a whole week procrastinating, never doing the really big recruiting task you have been avoiding. You are really showing yourself to be not cut out for founder-life (at least within your own mind, we’ve all done it). You could feel guilt and shame. Or, you could follow these three steps:

1. Admit the failure without excuses, bargaining, or caveats.

You will be sorely tempted to allow excuses, to pass off some amount of the blame. But if you do this, however transparent the attempt is, it may con your own mind into believing you. The minute you decide external circumstances created your situation, is the minute you lose control over it happening again. Learn to observe the excuses you tend to make, and catch them before they take hold. Just clearly say: “I didn’t do what I was hoping for this week.” and leave it at that. It can be uncomfortable to just quietly sit with the pain of failure, but it’s a powerful exercise.

2. Say the magical incantation

“I did the best I could with what I knew and who I was, but tomorrow I can do better.”

No one chooses to fail. It sucks. It’s very unlikely you would have chosen it, if you had the choice. Your motivation is a product of your environment and experiences, not something you can consciously control all the time. We can improve it over time, but you can’t expect yourself to come out of the gate perfect. Even in failure, you were doing what you could.

3. Make any type of plan which could improve things next time

This can be any plan at all. It can be as simple as scheduling time next week. Or making an outline, so when it’s time to do the work it’s easier. Or asking a friend to keep you accountable. Any legitimate experiment which has a shot at revealing why you failed the last time. Even if your experiment doesn’t improve things, you will eventually find one that does.

This formula is magic. Step one is the simplest, the most important, and the hardest; Once you clearly state your failure (even if your plans suck), your brain will take note and steer you in a new direction! No shame required.