An Incomplete List of the Things I’ve Done Wrong


This post is inspired by Julien Smith‘s post of the same title.

1. My parents gave me $2,000 for graduating high school. I could see how proud my mom was to be able to give this to me. Instead of saving it, I ordered a new exhaust system and rims for my car. I crashed that car a few weeks later. She never said anything, but I think I let her down in a big way.

2. When I was 23, my dad left my mom. During the process I tried to be there for my mom. She decided to take him back. Shortly after that I became overwhelmed, pulled back, and basically told my mom that she had to deal with this without me. “I don’t want to be in the middle of this anymore,” I said. My wife and friends, who were just looking out for me, told me it wasn’t my responsibility to get involved. But I regret not sticking by my mom’s side to the end, even if I thought she was making the wrong decision. I also regret not being there for my dad even though he was in the wrong.

3. I didn’t spend enough time with my childhood dog. She was a gift from my parents when I was 9. She loved me unconditionally, but sometimes I ignored her. She deserved more.

4. I only applied to colleges in Missouri. I can’t really remember why I didn’t look outside of my home state. Knowing my past self, I would have loved NYU or Colorado or London or somewhere near mountains or oceans. Maybe I wouldn’t have been accepted, but I’ll never know because I didn’t apply.

5. I didn’t leave the country until I was 20. Traveling has given me new perspectives and relationships I can’t imagine not having. I wish I had traveled a LOT more in my teens and twenties.

6. I ran track in high school but I never exercised regularly after that. I’m pretty skinny and I appear fit, but my back and neck muscles are very tight and my six pack turned into a blob. My energy levels are lower than I remember them being when I was in shape.

7. I was fortunate to get hired by Startup Weekend, a non-profit that I had been volunteering at. I worked there for about a year as their COO, helping them grow 10x. I abandoned them for a job at a sexy startup, which failed. Hindsight is 20/20 and I made what I thought was the right decision at the time, but I regret it. I left too early. I think I let them down in some ways.

8. In middle school I got pushed face-first into a locker by a kid named Greg. Greg was a popular kid and a full head taller than me. He wanted to fight me. I never found out why. I lowered my head and quietly mumbled that I didn’t want to fight him. He pushed me again. A teacher broke it up before it got serious. I should have punched that kid square in the face. I saw him bully dozens of other kids over the following years. Maybe I could have prevented some of that.

9. I didn’t read enough as a kid. Now I feel like I’m playing catch up to absorb as much knowledge as my peers and competitors.

10. I spent all the free time I had in college watching 24 and partying instead of starting a company or learning to how to code.

11. I dropped my Spanish minor because it was hard.

12. I majored in Business. What a waste. If I could do it again, I would study Psychology, Information Systems, Philosophy and Spanish.

13. When I was working at an investment firm, my boss convinced me to get an MBA. He even offered to pay for it. The first semester felt like a review of undergrad. So did the second. I learned nothing but I kept going for a full year. Then the firm terminated its tuition-reimbursement program and I was stuck with the whole bill. When I left the firm to join Startup Weekend, I dropped out of the MBA program. So far, it was the biggest financial mistake I’ve ever made.

14. This one is bad. In elementary school, a rumor started that one of my classmates (a boy) tried to have sex with me. I was called into the Principal’s office. The other kid was sitting there when I walked in. When the Principal asked me if the rumor was true, I said yes. I can’t remember why I lied. I think the whole situation scared me. The Principal scared me. But it doesn’t matter – it was wrong and cowardly. An opportunity was given to me to stand up and be a man, and I failed. The kid had to go to counseling. Years later he announced that he was gay. I wonder if the experience I put him through because of my cowardly lie caused him to stay in the closet for a bit longer – to be a little bit more scared than he would have been had I told the truth like a man of integrity should have.

15. I loved soccer as a kid. My dad was the coach and our team’s name was the Red Barons. I wasn’t the most skilled kid on the team, but I was known for getting the team energized by scoring the first goal. I usually did this by running straight at whoever had the ball and screaming, getting right in their face before they kicked the ball. Often that meant a kick to the face, but it also meant I could get the ball and score. I wish I had kept playing soccer.

16. I tried to start a chapter of Delta Epsilon Chi in college but gave up after a year. We had the money, the members, and the support of the Dean. I can’t remember why I quit.

17. The biggest regret of all is wasting countless hours thinking about all of the above. I can’t change any of them. Like Julien said, none of this matters. Life isn’t made up of the things you did wrong. It’s made of the things you did right.


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