18 Expensive Mistakes That Taught People Money Lessons The Hard Way
"I'm still not done paying for it monetarily and emotionally."
If you're a human being living here on planet Earth, you've probably made some mistakes. It's kinda what we do. But some mistakes cost a lot more and can be much harder to recover from than others.
1. "Definitely a DUI. You are required to take a class for Alcohol Awareness if you get a DUI (at least in Texas). The man teaching us had us write how many drinks we drank the day/night we got our DUI. Then he made us add up all of the costs we have had to pay since then and divide it by the number of drinks we had. After bail, lawyer costs, Ignition Interlock monthly charges as well required classes, turns out I had spent thousands of dollars per drink. Most expensive drink and mistake I have ever made in my life, and I'm still not done paying for it monetarily and emotionally."
2. "Not signing a prenup! It doesn’t matter who you think you married — sign the damn paper. So far it’s cost me my house, mental health, and $90K, and we haven’t even signed the divorce papers yet."
3. "Picking the grad school I went to. I am not one of those people who regrets college or grad school; I love my job, and I wouldn’t be happy in another profession. But I chose a more expensive school because I didn’t know what to look for in a grad school, and I wanted to live in and explore a new city."
"The latter I have no regrets for because I met new people and had a wonderful time! But my school is run by sharks who pretend to care about students (not the professors, they were fantastic!). We paid $80,000 for the entire program, but they refused to give us a tuition break when we went virtual. Eventually, they so generously gave us $160 back. We had no access to all the resources we were promised, and when we graduated, and none of us had any practical experience. Wouldn’t trade my friendships or experiences outside of school for anything, but part of me wishes I went to a more reasonably priced school closer to home."
4. "I decided to spend the holiday break in Oslo and not plan too much so I could just relax. Well, I didn’t look closely enough at my plane ticket, and the airport where I landed was a 45-minute train ride from Oslo and my Airbnb. I had to spend the night in a motel because the last train had already left."
5. "I foolishly wrote a reference for a friend on company letterhead and left a copy on the work printer. Got found out, fired for gross misconduct, and lost $10K in redundancy payout."
6. "I cracked my sink with a Crockpot. The Crockpot was fine, but I put a huge crack in our kitchen sink by dropping the insert when I was cleaning it. It cost $400 for a new sink and $500 for install (farm-style, under counter, really tricky to do yourself). Yeah...needless to say, I have a VICE GRIP on anything I'm washing in the sink now!"
7. "I worked at Toys 'R' Us for many years, and one holiday season I was working customer service and accepted a return for a PlayStation 3. The box seemed to weigh the right amount, and I checked all the seals — they were intact. Turns out the PS3 I returned was actually just a big rock and a phone book stuffed in the box. One of my supervisors took the rock and wrote '$600 ROCK' on it, and it was kept as a door stop in the store until it went out of business a few years ago."
8. "Freshman year of college I wanted an excuse to drive around with the guy I liked, so I offered to drive my buzzed roommates to a party in one of their cars, since I didn’t have one. It was really dark, and there was a tiny curb that jutted out into the road — easy to spot in the sun, not so much at night. We weren’t even one minute into the drive when I hurled the car over the curb and popped massive holes in TWO of her tires. It cost me $400 and a new reputation as an incredibly shitty driver 😭."
9. "After working 60-hour weeks for 6 years in my exhausting but well-paid corporate job, I saved up and got into a franchise system. They convinced me it would be fairly profitable, and I was stupid enough to believe it. Turns out all my profits went to the franchise system, and I worked my ass off for free. I could not get out of the contract for five years. I lost €140,000 [$186,000] in initial investment and had to put in a total of about €60,000 [$79,700] just to keep my head above the water. Now my retirement money is gone, I have a huge credit card debt, and I am starting from scratch at age 39."
10. "I got so frazzled trying to buy Coachella tickets, which are expensive enough as it is, that I somehow accidentally bought two VIP tickets. I was only able to sell one, so I was stuck with a VIP wristband while the rest of my friends were general admission. At least I got to go to the bathrooms with shorter lines? That’s what I tell myself."
11. "I accidentally hit the gas instead of the brake and drove through a garage door...on a Friday afternoon in the middle of February and just before a significant snowfall 🤦♀️."
12. "I was manic and went shopping with my credit card. Maxed it out at $3,000. I was so embarrassed, and it's frustrating because in that moment I just didn't care."
13. "I went on a trip to Italy and rented a car to drive around the country without realizing they have tooooonsss of rules that need followed beforehand. One of these rules is that there are certain zones that you can only drive in if you have a special permit and they’re sign posted. Guess who got lost and drove around the Colosseum three times and ended up with three separate traffic tickets?"
14. "When I was 16 I travelled to Wales to fit loft insulation with a pair of strangers who worked for my football manager. I didn’t have a clue what I was doing. In my first house, instead of walking along the beams I put my foot through the ceiling and destroyed someone’s bedroom."
"I was supposed to be away for five days, and they brought me home after 24 hours LOL. Not only did they have to pay for the repairs, but they had to cancel every other job because I was too much of a liability."
15. "Blowing through my inheritance while struggling with grief. They say that you should not make any expensive purchases in the first year of grief, and I definitely support that advice."
16. "About a month ago, I crashed a perfectly good car into a telephone pole! All because I looked at my smart watch for two seconds. Between the cost of renting a car in the interim and buying a new one, it's the dumbest and most expensive mistake I’ve made."
17. "I bought a house right before a recession, and it got repossessed. I will likely be paying back the mortgage shortfall for the rest of my life."
18. And finally, "I come from a Latino background where it’s normal to live with your parents until you're married (no matter what age that is). I regret not taking advantage of the fact that my parents never asked me to pay rent or help with any bills after I moved back home from college. Since it wasn’t expected or demanded of me, I basically spent every paycheck I got on material things."
"Fast-forward years later, I’m married but I still have a bunch of credit card and student loan debt. If I didn’t focus so much on spending my money back then, I would have so much more in my own savings account now, and I could contribute more to mine and my husband's combined bills. I’m incredibly lucky that my husband loves me, is smart with money, and is willing to help me. But sometimes I get so down on myself, and I feel like I don’t contribute anything to our marriage aside from cooking and cleaning. If I could, I would go back in time and SAVE my money so that I wouldn’t have to be in this mess I created for myself."
Note: Submissions have been edited for length and clarity.