Reddit user Dira_Jo asked the community, “What do you consider the worst financial decision of your life?” People swiftly took to the comments to share the money mistakes that still haunt them years later. Here’s what people revealed:
1.“Not contributing the max amount into my 401k. I worked at that company for 27 years and could’ve retired long ago.”
2.“Being a tobacco user. I’ve told all my friends younger than me, as well as my kids, never to start using tobacco or Nicotine products. I started at 18 and am almost 45 now. I’ve quit a few times for a while, but a ton of stress at work and other things brought me back. I’ve spent too much time and money both using, trying to quit, and dealing with ridiculous price increases and taxes that are supposed to help deter but really just squeeze more from us addicts.”
“I have lived the rest of my life very responsibly, living within my means. I bought a home and then sold it once my family grew to purchase a bigger house while the market was still decent here and interest rates were low. I’ve invested the max in my 401k. I buy used vehicles and pay them off as soon as possible. The wasted money comes from something I know is bad for my health in the long term. I have to admit, I have little control over it, although I keep trying. It sucks. So, any of you younger folks here, take it from me. It may seem fun, cool, or relaxing as a teen or young adult, but do yourself a favor for both your wallet and health and stay away from dipping, smoking, vaping, etc.”
3.“Loaning money to friends. Or anything of financial value, for that matter. To this day, I will not loan so much as a penny without some kind of leverage against the person to pay me back. That saying about loaning people money is true. If you’re going to loan money to somebody, you should do it assuming you won’t get paid back. That has happened to me every single time. I will never loan money or things of monetary value ever again.”
4.“Letting my dental insurance lapse. I had the same plan for years, plan options changed, and I forgot to update to the new plan. I got my first cavities and root canals a few months later, and it cost thousands rather than hundreds.”
5.“I was short on rent by $500 in 2013, so I sold 16 Bitcoins to cover the difference. Those coins are worth over a million dollars today.”
6.“My first trip to college. I racked up $56k in debt, and I dropped out. The cost of campus housing was more than the tuition, and the program was garbage. The school later lost its accreditation and went out of business. Students with federal loans had their balances discharged, but mine were private. I wish I had done some serious soul-searching at the time and thought longer about my goals and career path, but live and learn.”
7.“My children. They’re the best emotional decision ever, but the tiny accountant in my head reminds me every time I book a hotel or buy plane tickets for a holiday how much nicer of a holiday I could afford if we’d stopped at one. Don’t even get me started on how much it costs to eat at a restaurant for a family of six, especially now my oldest thinks she’s too grown up for the kids’ menu.”
8.“Selling a house for $368k, which is now worth $800k! I could have built an ADU and retired early!”
9.“During the pandemic, two of our four kids decided to move back in with my wife and me. I had some assets, and we were getting the pandemic subsidies then, so we eliminated our debt and built up a decent nest egg. Rather than moving to a larger house, we converted the garage into a studio apartment the boys could share. That A) severely devalued the house (even more so because the work done was subpar at best), B) put me back into debt, and C) forced me to sell my assets, which would have been worth so much more if I hadn’t sold it at the height of the pandemic.”
10.“My big sister called me in 2006 and said, ‘Wanna buy a condo?’ I agreed. That was the worst decision of my life. Not just financial, as the collateral damage was also severe. I experienced depression, which assisted with the loss of a job and loss of relationships. Eventually, I filed for bankruptcy to achieve rock bottom, and then I clawed and scraped my way back up. But, this was in my early/mid-30s, which is generally considered a real breaking point in a person’s life.”
11.“I filed my own taxes incorrectly for three years. I hired a tax accountant on the fourth, realized I had reported my rental income improperly, and owed about $35,000. Didn’t have it on hand (duh), so that hurt.”
12.“I was 22 and really financially dumb. I had $70,000 in student loans. I let Wells Fargo convince me that combining my private and federal loans into a single consolidated private loan was better. At the time, no federal loan relief options were available to me. Now, 15 years later, I’ve paid approximately $50,000 and still have a balance of $60,000, and Biden went through a federal loan canceling spree that I was no longer eligible for.”
13.“Buying a timeshare in a foreign country without fully understanding the language or legal system. Lost more money than I care to admit.”
14.“Back in my mid-20s, when I started making good money, I purchased an extremely expensive sports car that I was paying close to $1,000/month on.”
15.“I got talked into selling skincare and makeup products in the early 2000s. For some reason, I thought it was a good idea to order $2,500 worth of inventory to start with. Ugh, they made it sound like it would fly off the shelf. I spent several years paying off that credit card because the products did not, in fact, fly off the shelf. I still cry badly about this 20 years later.”
16.“In 1991, my then-wife and I were looking for houses. We found one that was 2,000 square feet and lakefront. The house needed repair and was a repo with lots of water issues. I am a carpenter; in 1991, I was still an apprentice. We bid $65,000, which was the only bid they received. They accepted. She worried that we couldn’t afford it. I think I was making about $13 an hour at the time. So, we asked for our earnest money back, and they gladly gave it back and sold it that day for $90,000. Fixed up, the house would have brought $200k back then and probably $500k today. It wasn’t that bad; structurally, it was sound. And we both loved to fish. It’s easily the one that got away from me.”
17.“Starting a business in an industry I knew nothing about at the ripe age of 26 (with a family member) in May 2021. I went from being extremely financially independent (starting at the age of 16) to absolutely destroying my credit, accruing legal fees and so much debt, now approaching 30.”
18.“Not selling my stocks right when COVID’s impact on the market started reversing. I had about a 400% ROI but decided to hold onto them, and now I’m at about 50%.”
19.“Graduate school. Fortunately, I’m not in debt for it, but every job I have applied for in the field turned me down; the other jobs in that field are either beginner part-time jobs or administrative positions I don’t have experience in. To add salt to the wound, the job I have now pays better than any of them, and it only requires a high school diploma.”
20.“Marrying someone without realizing how terrible they were with money or how their bad financial management would impact me even after we were divorced.”
21.“Chasing the meme stock hype at the peak of the GME/AMC craze. I lost about $7,000, which isn’t the biggest issue. It was the fact that I fell for the hype while being an inexperienced trader, and I also did it behind my wife’s back with money that should have never been in the market. It was just raw, unrestrained ignorance. I still get mad at myself when I think about it.”
22.“I bought a used car that turned out to be a money pit. The seller worked at the equivalent of the DMV, so I figured he wouldn’t lie when saying that the car had never been in an accident, was in good working order, etc. Turns out he lied. I spent more on repairs than I paid for the car.”
23.“Taking out a loan to pay my husband’s debts. He’s now an ex while my ass still has to pay.”
24.“I was in my early 20s and moving across the country. I had most of my savings (about $2,000) in an envelope for some godforsaken reason — I suppose because I would switch from a bank to a credit union in my new state. Somewhere along the drive, I stopped at a gas station, paid cash for my gas, and drove a hundred miles before I realized I left that envelope on the gas station counter. I really hope the gas station attendant really needed it so that it at least benefitted someone.”
“Much later in life, I made a bet with someone about the outcome of a book. I lost the bet and transferred one Bitcoin to a stranger online. This was when the price of Bitcoin was in the $6,000 range. Both setbacks felt like huge deals at the time. The first was because $2,000 was almost all of my savings then; the second was because I felt so silly to bet such a large amount online (given that I had never really gambled before or since). But neither was as big an investment as my latest car or the house I’m buying. Ultimately, even these major setbacks have had very little to do with how much I financially have today.”
25.“I didn’t invest my money earlier, so it’s been sitting in my checking account for years. I started investing when I was 32. Had I done it five years prior with the money I had then and the amount I have invested since, my profit on them would have been double what it is today.”
26.“Not moving on to a higher paying job and taking that leap of faith. My current job has downsized so much just to operate within a subpar budget. They haven’t given out cost of living increases in years, and now I am quickly approaching retirement. If you are unhappy with your job, just get the skills and training you need and move on, especially if there is no future in the company.”
27.“Turning down a $40k scholarship because my mom wouldn’t let me visit the college. It was my dream school. I transferred there with a $4k scholarship they offered. If I had taken their initial offer, I would’ve only had maybe $10k of student debt. Now I’m $55k deep.”
28.“Being overly conservative and not buying a ‘forever’ home back in 2019. My budget is way higher than when we were shopping in 2019, and I can’t afford to move anymore. I learned that you can’t grow old in a house without the primary bedroom on the main level. Also, living close to a good hospital is so underrated. I’m nowhere near retirement age, but health issues can take you by surprise, even when you’re young.”
29.And: “I’ve just generally been too reckless with money in my life. I haven’t ever really made any single huge financial mistake; I’ve just made a large number of smaller impulsive money decisions that have led to me having very little saved. I am currently working on it, though, and I am doing better.”
What’s the most significant financial mistake you’ve ever made? Tell us in the comments or submit your story anonymously using this form.
Note: Submissions have been edited for length and/or clarity.
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