Bootstrapped startups and the shit I learn in therapy

As part of my 2021 reflection, I imagined myself in my 80s, writing a letter to my 28-year-old self. Here is what I wrote.

Dear Andrew,

Don’t worry. You will live a life full of adventures. From starting a business, to hiking the Camino de Santiago, to traveling all over the world to climb mountains.

Don’t worry about discovering climbing later than you wanted to, you will have plenty of time to climb. While you may not ever be a world-class climber, you will find incredible friendships and joy in the pursuit. Remember that it’s not about the grade, it’s about the mental lessons, clarity, and of course the relationships.

All of life is really about the relationships. You understand this already to some degree, but it will become more and more clear as people come and go from your life. Cherish your time with them, be present, and be kind.

If I can offer you a couple pieces of advice, be honest with yourself and do the hard work. Deepen your empathy, and keep working to build patience and perspective. You will regret moments of anger, insecurity, and selfishness, but you will never regret moments of generosity and kindness.

You have always struggled when things aren’t fair. You have a deep desire for justice and equality, and that is beautiful. But it can also lead you to a place of anger, judgment, and self-righteousness. Life isn’t fair. And your perspective matters so much. Giving and doing for others, even when it is lop-sided, doesn’t have to feel like a burden if you don’t want it to.

You also need to learn to recognize when your frustration with others is frustration with yourself. Rather than trying to change them with guilt or stern words, change yourself first and lead by example. Show them love and understanding. Ask questions to understand where they’re coming from. You’ll likely end up understanding yourself better as well.

Lastly, be kind to yourself. I know I have been giving you advice that indicates you have a lot of room to grow. You do. But so does everyone. It’s okay, you’re doing your best, and I love you. Even if you don’t always love yourself yet. (You've come a long way on this front, keep it up).

Give Maddy a kiss, play with Po Boy and Stevie, relish your time in Detroit, give Papa a call, take a trip just to hang out with Mom and Dad, make sure Abby knows how much you love her. The rest will work itself out.



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