Bootstrapped startups and the shit I learn in therapy

"I'll be fine as long as the company doesn't go under... and my dog doesn't die," I told my therapist.

"How old is your dog?"


It was the beginning of 2019, and I was going through a tough time. I had ended a two-year relationship where nothing was obviously wrong. Stress at work was at an all-time high. I had my first (diagnosed) panic attack.

But this wasn't really new. Looking back, it had been building for a long time. And it wasn't hard to see the trend.

I've written before about how becoming an entrepreneur gave me purpose. Starting my company Krit taught me that I wasn't lazy, and opened my eyes to what I could accomplish. In a lot of ways, I feel built to build companies.

That's the problem.

Why are values important?

People talk a lot about values, but why do they actually matter?

Core values are the beliefs that we all hold close. They're the stories we tell ourselves about who we are, and how the world should be. Whether you know what yours are or not, you have them.

Going back to your values is extremely helpful when facing a tough decision. If you're not sure what to do about a problem, ask yourself what someone with your values would do. It's a way to get some distance and see the issue from a new angle.

They're also helpful in keeping a group of people moving in one direction. Fancy pants CEOs like to call this alignment. Two people with the same set of values may disagree about how to best solve a problem, but they'll both want to solve it all the same.

Understanding your personal values is important for another reason... self-regulation.

Self-regulation is the ability to regulate your moods without external influence. It might be the single most important skill you can develop if you want to lead a happy life.

The problem I regularly face, as do so many ambitious people, is that my identity is tied up in my work. As an entrepreneur, this is especially risky because it's risky work. At some point, I will probably fail.

If Krit goes under, and I see myself first and foremost as the leader of Krit, what happens to me? At that point, it makes sense that I'm a failure.

If my identity is Duck's dad (Duck is my dog) and Duck dies... then I'm nobody.

My Boykin spaniel Duck, standing in a corn field
A picture of Duck being Duck to lighten the mood

The solution is to build your identity around your values

Any time you place your self-worth on something outside of your control, you're running the risk of making yourself miserable.

But your values are always under your control. You choose how to act every day. You get to decide if you want to act like the type of person you want to be. Your company could fail tomorrow for reasons totally outside of your control. But if you don't make the courageous decision, or the kind decision, that's on you. And if you fail despite following your core beliefs, you can either reevaluate your belief system or rest easy knowing you did everything you could.

How to find your personal core values

Discovering your personal core values is tough. It requires introspection, and deep thought. But it's an incredibly rewarding exercise.

Here's the process my therapist walked me through.

Start with a large list of common values. Here's the one I used.

Go through the list, word by word, spending no more than 5 seconds on each word. Every one that jumps out at you, resonates with you, make a note and move on.

If you're like me, you'll end up with a list of about 30 words. Now comes the hard part. Weigh each word and cut out any that aren't a part of your deepest held beliefs. This takes time, and it's all about trade-offs. You might have similar words. Weigh these to decide which one feels the most right.

Keep going until you have 3-5 core values (more than that is just too hard to keep up with).

What are my values?

After going through this exercise, I picked 5 values that embody the person I want to be.


Fear is healthy, letting it paralyze you is not. I never want to make a choice simply because I'm scared of the other options.


Connecting with others and putting yourself in their shoes is a superpower. Empathy helps you communicate better, create more meaningful work, and live a happier life.


Be honest with others and yourself, always. Some of the worst times in my life have come from lying to myself. Honesty can be scary. See Courage.


I'm more fulfilled when I'm creating, exposing myself to new ideas and thinking outside of the box.


No amount of success is worth it without love. Love for my friends, family, strangers, and romantic love. Treat others with love, treat yourself with love and surround yourself with people who are full of love.

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