1. Working my ass off getting 3 useless degrees. I fell into the trap of believing that high grades and multiple degrees = good, stable, high paying jobs. Lmao. Looking back I can’t believe I was so naive.
2. Got stuck on my balcony before work one morning. Door latched as I shut it. Was approximately 6 feet off the ground, so I decided to jump off. Landed on my feet. Grass was wet, feet slipped… fractured three vertebrae, spent nine months in a hospital bed.
3. Bringing on a sleazy business partner whose shenanigans put me under. Even twenty-five years later, if he stepped in front of my car, I would not even think of tapping the brakes.
4. I skipped a class for organic chemistry in college before finals. Didn’t get the memo that final exams would be given in a different room. Showed up 45 minutes late and my professor would not let me in. I failed the class and nearly failed out that semester. I was on academic probation after that.
5. Dorky guy in our graphics lab at school tried convincing us to buy Apple stock while we struggled with our awful PowerPC 6300s. “They rehired the CEO they fired! He’s a visionary!” Riiiight.
6. Not watching a movie with my dad before he died of cancer. He asked me one day if I wanted to watch old films with him. I declined because I said I needed to work on school stuff. He passed a month or two later, and it remains my biggest regret.
7. Meth, just once, for about 10 years straight.
8. Got offered an internal promotion for double the salary as a JavaScript developer at a UK FTSE 100 company. Declined because I was humble about my skills and didn’t want issues. Now, years later, I realize everyone is winging it and I would have been fine with 20 hours on Udemy.
9. Talking to police without a lawyer. Do not do that, kids…
10. Leaving the Coast Guard after four years. I’d be retired with a full pension now and still could have had another career.
11. I do not feel like I made any major mistakes. Just a long chain of small, seemingly inconsequential ones that stacked on each other. Sometimes it feels like my entire life is a gigantic mistake without beginning or end.
12. When I was a kid we rode our bikes to the top of a hill and sped down a sidewalk pushed up by tree roots to hit sick jumps. No helmet. My bike’s front wheel and handlebars loosened. Landed, bars were straight but the wheel sent me into a tree. Knocked out cold. People say my personality, handwriting, and grades all changed after.
13. Believing teachers, professors, and family who told me I was naturally bad at math. Turned out I just needed the right teacher to explain the reasoning behind it. Once I understood the “why,” math became easier.
14. Letting go of someone who was really good for me because of depression and insecurities. Now I’m alone because of it.
15. Ironed a shirt while wearing it and burned my nipples. Had to put plasters on them for weeks. Alcohol may have been involved.
16. Trusting the wrong person with important secrets.
17. Quitting college to take a management promotion at a fast-food job.
18. Trying heroin. Spent six years chasing that dragon. I am now five years clean though.
19. Toss-up: either the first drink I ever took in secret or the drink I took this morning in secret. Hard to decide.
20. Not putting money away early enough. Start early. Make it automatic.
21. Getting married — or more accurately, marrying the wrong person. Married in 2001, divorced in April. She cheated repeatedly. Four kids by four men, one of them mine. Just the tip of a depressing iceberg.
22. Not paying off my mortgage 17 years ago when I had the money. Used the cash to renovate instead. If I had paid it off, I’d have an extra $3000 a month today.
23. Putting absolutely everything I had into getting a degree and a job in a field I do not care about. Now I am stuck in a job I cannot stand because I will never make this much money again.