35 Mistakes I’ve Made on My Way to 35

You can’t avoid mistakes, but you can make better ones

Most people spend their lives repeating the same mistakes over and over.

There’s a quote by Ernest Hemingway I love that says “There are some things which cannot be learned quickly, and time, which is all we have, must be paid heavily for their acquiring.” The first time I read that it took away my breath because I’ve learned how true it is.

If you don’t want to spend your life on a hamster wheel, you have to learn from your mistakes. Most people know that in theory, but it’s one thing to know and another thing to practice. I don’t pretend to be a pro at this. But the longer I live the more I see how my habits and mistakes affect me.

I recently celebrated my 35th birthday. To mark the occasion, I thought I’d take this opportunity to reflect on what I’ve learned from 35 of my biggest mistakes, in hopes that it will help you too.

1. I thought I was special. When I graduated from college, I was sure the world would open up for me. I didn’t. Nobody cared how destined for greatness I thought I was. But because I thought I unconsciously thought I was special, I didn’t always do what I needed to do to grow and become the person I wanted to be. You don’t get to skip the process.
2. I didn’t grow where I was planted. Robert Greene popularized the idea of alive time vs. dead time. Alive time is when you actively pursue growth, dead time is when you passively wait for something to happen for you. When you’re in a situation you don’t like you always have a choice: will you make your time alive time or dead time? I haven’t always made the right choice. Thankfully, understanding this concept has helped me make better choices.
3. I expected talent to carry me. When people tell you you’re good at something, you start to build your identity around it. For me, it was public speaking. I was sure I’d be an in-demand speaker and change thousands of lives with my words. But there’s a lot that goes into supporting and nurturing talent. You don’t get to perform all the time and leave the unglamorous work to someone else.
4. I overthought simple decisions. “I swear to you that to think too much is a disease,” said Dostoyevsky. I’ve been guilty of causing myself more stress than necessary by overthinking even simple things. The good news is I’ve learned to make better decisions. How do I do it? By accepting that even if I make a mistake, I can probably fix it later.
5. I didn’t listen. Have you ever been advised by a professional, but you thought you knew better? Going against good advice may work out in your favor sometimes, but other times it will blow up in your face.
6. I stayed too long. More than once I’ve gotten stuck in a situation I knew I needed to leave. Do you know what kept me there? Fear. I was haunted by the question “What if…?” But life is too short to constantly fear what might go wrong. Franklin Roosevelt was right, “The only thing we have to fear is fear itself.”
7. I didn’t pay attention. Letting my mind wander is one of my biggest faults, just ask my wife.
8. I didn’t trust my gut. “There is more wisdom in your body than in your deepest philosophy,” said Friedrich Nietzsche. We often try to use logic to make decisions or solve problems at the expense of what our body is telling us. Every time I didn’t listen or pay attention to my gut, I regretted it–no exceptions.
9. I held on too long. Some dreams are supposed to die. As painful as that is to accept, once you do you can get on with the business of living. If you want a chance to thrive in life, you have to let go, and do it often. There is no use clinging to a dead dream while life goes on all around you.
10. I played the short game. Google probably ruined my generation. The ability to get an answer or information you want in milliseconds is addicting. Don’t think it doesn’t carry over into other parts of your life. I’ve started my share of projects and given up because they were going to take too long. As I’ve gotten older I’ve learned if you want a chance to win, you have to play the long game.
11. I tried to follow someone else’s path. We love reading stories about other people’s success. We look at pictures of our favorite influencers on social media and imagine what it would be like to live their life. The problem is their story isn’t your story. You can’t be someone else, and you can’t follow the same path to success. I know, I’ve tried.
12. I let myself become resentful. I love the story of Cain and Abel in the Old Testament. Each brother brings a sacrifice to God, and God accepts Abel’s sacrifice while rejecting Cain’s. Full of rage, Cain murders his brother. Like Cain, every time I’ve let myself become resentful I want to tear down and destroy what I can’t have. Have you ever felt that way?
13. I ignored the warning signs. Catastrophic events rarely come without warning. It takes some time to learn to listen to the signs. I’ve failed at that more than once. Do you know what keeps you from listening? Pride. You don’t want to think it can happen to you.
14. I expected it to be easy. There’s an old saying, “Expect it to cost twice as much, take twice as long, and be twice as hard as you think.” If you’ve ever taken on a big project, you know there’s truth in that. More than once I’ve made the mistake of thinking something would be easy, only to face defeat when it turned out to be much more difficult than I imagined.
15. I expected it to be hard. On the other hand, not starting because you’re afraid it will be too hard can cause you to miss a great opportunity.
16. I tried to control the outcome. The Holocaust survivor and psychiatrist, Viktor Frankl, introduced me to the idea of hyper-intention. It’s when you focus so much on getting a specific outcome you’re unable to accomplish it. You can want something too badly, and you can try too hard. I’ve achieved my biggest successes when I let go of needing something to turn out a certain way.
17. I told myself a crappy story. The story you tell yourself about yourself determines your quality of life. If you believe you’re a loser who can’t complete a project, you’ll act on those beliefs. This is basic psychology. Every time I’ve told myself a disempowering story, I’ve suffered.
18. I quit too soon. It’s one thing to know when to quit, it’s another to know if you’re quitting too soon. Sometimes the urge to quit comes when a breakthrough is right around the corner.
19. I said “yes” when I wanted to say “no.” Pretty self-explanatory. Sometimes the best answer is just “no, thank you.”
20. I was scared to invest in myself. The first writing course I ever bought was $400. I’d never made an investment in myself like that before. Every time I’d had an opportunity in the past, I passed on it because it was “too expensive.” I followed the course all the way through and a couple of months later I’d made back double what I spent. Not every self-investment turns out that way, but each one adds value.
21. I went along with the crowd. If you spend a lot of time with people who believe in something so deeply they’ll shut you down if you question them, you’re probably hanging out with the wrong people. Sometimes, it’s hard to voice a different opinion when everyone else seems set. But bad things happen when people blindly follow a person or idea. As Nietzsche said, “Madness is rare in individuals — but in groups, parties, nations, and ages it is the rule.”
22. I was too nice. I’ve learned the difference between being nice and being kind. Being nice means you’re trying to make everyone happy and never upset anyone. Nice people get walked on and abused. On the other hand, being kind means treating others with respect. It also means holding firm boundaries. Every “nice” person I know is deeply resentful because they don’t understand why people aren’t as thoughtful as them. Practice kindness and you can make the world a better place, and stay mentally healthy while doing so.
23. I wasn’t present in the moment. I don’t remember much about my oldest kid’s second Christmas. I had to work the day before and after Christmas that year and I was mad. I’d never had to do that before. It’s a stupid reason to get mad, I know, but it was a big deal to me then. But my oldest kid will never be two again.
24. I made my happiness circumstantial. I’ll be happy as soon as I [fill in the blank]. Have you ever thought that before? Happiness isn’t worth postponing until someday down the road. Make it today.
25. I tried to get everything right. I’ve never been much of a perfectionist, but I’ve wasted enough time trying to avoid making mistakes. It may take the form of overthinking or obsessing over some unimportant detail. But it’s better to take action and make mistakes than spend precious time running in circles.
26. I used the wrong measurements. Social media is not real life. Social media is not real life. Say it with me this time–social media is not real life. You can’t measure your real life against someone else’s highlight reel.
27. I overcomplicated it. Sometimes the best thing to do is start something and fix your mistakes as you go. It’s easy to get caught up in researching and planning and think you’re making progress. “Joy’s soul lies in the doing,” said Shakespeare, which explains why inaction breeds anxiety.
28. I trusted certainty more than faith. My faith has always been an important part of my life, but I’ve learned that faith doesn’t usually mean certainty. As Anne Lamott says, “The opposite of faith is not doubt, but certainty.” Some people trust in the unbending nature of certainty and lose the mystery of faith.
29. I had faith when I needed facts. I once started a non-profit organization that failed after two years. I had a lot of faith that things would work out, even though the facts told me otherwise. I started the organization knowing that these types of ventures had an overwhelming failure rate. There is a time for faith and a time for facts. Both are important, but so is knowing when to rely on each.
30. I was too uptight. If I could go back and give my younger self some advice, I would tell myself to relax. Enjoy the ride and the moment and don’t give so much attention and energy to some imagined future destination.
31. I took responsibility for other people’s happiness. You are responsible for your experience in life–that much I know for sure. So why, then, do we take the responsibility of trying to make someone else happy? You can contribute to their happiness, but you cannot make someone happy.
32. I forgot about death. I heard about a graduation ceremony where the speaker began his speech by telling the students, “You’re going to die.” As shocking and perhaps inappropriate as that may seem, it’s actually incredibly motivating if you know how to use it. How many times have I put off doing something important because I arrogantly thought I would have time later? Death is the engine of life.
33. I thought my life was over. The poet Robert Frost said, “In three words I can sum up everything I’ve learned about life: It goes on.” Your story isn’t over. Nobody’s had the last word over your life. If you’re still alive, the sun will rise again on you. My life wasn’t over, it was just rearranging.
34. I tried to go back to the way things were. When you go through a dark period, all you want to do is go back to the way things used to be. But deep inside, you know that’s impossible. Why? Because you are not the same person you used to be.
35. I forgot to live. There is a scene in Harry Potter and the Sorcerer’s Stone where Harry’s mentor, Dumbledore, shows him a mirror that reflects your greatest desire. “Men have wasted away before it…” Dumbledore tells Harry, “It does not do to dwell on dreams and forget to live.” Spending your time regretting the past or wishing things were different is a waste of your limited life. You can go on living, perhaps differently than what you imagined, but you can still make something wonderful out of life.

Everyone makes mistakes. The important thing is that you learn from them and try not to make them again.

I have made all these mistakes and more, and I’m probably better because I made them. You can’t go back and change things. All you can do is keep moving forward, armed with new knowledge and a resolve to be better. That way, you can make better mistakes.