Whether good or bad, financial decisions massively impact a person’s life. A loan, habit, or small mistake can derail an individual’s finances and set them back or leave them in debt for years — if not decades. However, many people don’t realize how much debt they have incurred until it comes time to pay it off…
1. “I once had a job with a startup, and the owner gave me unrealistic goals and told me that if I hit them, he’d make it worth my time. I had nothing else going on, so I said, ‘Okay, I’ll take that chance.’ I was salaried, so I was only being paid for 40 hours while working 60+ hours per week for about a year.”
2. “I spent $23,000 on chemotherapy for my pet cat, only for it to die anyway.”
“My wife and I have never set a hard number on our dogs’ healthcare, but there have definitely been times in the past when they were diagnosed with cancer, arthritis, or other ailments that we realized were going to cost a fortune and set us back financially.
At that point, It all comes down to: ‘Is this animal happy, young, and still enjoying life, or would they be okay with letting go?’ It’s always a hard decision.”
3. “Paying for insurance but not following through on claims. Before my honeymoon, I bought trip insurance — which turned out to be lucky because I had a medical incident and couldn’t go. So, I called the company to check if I was covered. They told me I was and to follow up with them in a few weeks. For some reason, I never called them back.”
“That was $5,000 down the drain.
Now, I follow up on both my insurance claims and anything else that might get my money back: warranties, refunds, etc. I refuse to leave money on the table out of laziness or convenience.”
4. “I didn’t file the proper form when I surrendered my house before foreclosure in 2016. It was one form — I didn’t realize it would be so important. I used an online tax service and was told by the collector that I would never hear from them again. Oh, how wrong I was…”
5. “I didn’t start saving for retirement until I was 40 because I grew up in a religious cult that taught me I didn’t need to save anything because Jesus would come back by the time I was 30.”
“Around 40, I finally began learning how to ‘adult’ independently. By the time I understood what a retirement account was, I was interested, but I had made too many financial mistakes to start saving money.
I began dealing with health issues, and my spouse was going through addiction, so there were a lot of aspects of life that kept me from making the right decisions for myself.”
6. “My husband and I bought a boat, and it only brought us pain. It was expensive to run and repair. We could never truly enjoy it because every time we took it out on the water, we were worried that something would happen and we wouldn’t have enough money to fix the problem.”
“It felt like a huge weight was lifted the day we decided to sell it to someone else. It’s often said the two best days in a boat owner’s life are when they get the boat and the day they say goodbye to it. That is 100% the truth.
I would never own a boat or anything that expensive ever again.”
7. “I’ve poured so much money into my parents’ financial situation. I’ve recently come to the bitter realization that their problems result from poor decisions and bad behavior on their part, and no money will ever dig them out of that hole.”
8. “When I was 20, my mom told me my student loans would just ‘go away’ if I couldn’t afford to pay them. I don’t know why I took her advice because she’s never been good with money.”
“About a year later, I got a call from my loan servicer informing me that my debt would go into collections if I didn’t pay next month’s minimum. I looked up what that meant and immediately made the payment. It’s been over a decade, and I’m still trying to pay off the interest.
So, yeah, I learned my lesson. It’s your money and your responsibility.”
9. “Getting into real estate. I own two rentals and the tenant recently defaulted on the only one that made any profit, so now we must evict him.”
“My advice is to stick with a mutual funds account. If you need money for an unexpected expense, you can’t just call your realtor and tell them to sell $20,000 worth of townhouse and send you the cash.
Mutual funds don’t call you at 3:00 a.m. to tell you the toilet is clogged. Mutual funds don’t suddenly need $50k for a new roof. Mutual funds’ neighbors don’t call you to complain about loud parties. Mutual funds don’t have tenants who neglect to tell you that a pipe burst in the wall. With mutual funds, you don’t live in fear that a vacancy will cause you to lose money out of your paycheck.”
10. “We built a home in a bad location that was too far away from friends, family, and activities.”
11. “For me, it was buying workout supplements — not steroids, but glutamines, BCAAS, pre-workout mixes. All because I thought one might work better than the other, etc.”
“I estimate that I lost $5-10k in a span of a few years. Then, one day, I just gave it all up.
I wish I had saved the money instead of going down that road, but lesson learned. I think part of the issue was that I lived at home with my parents and didn’t realize the value of a dollar or budgeting.”
12. “Impulse buying for myself and others who couldn’t afford the things they wanted.”
“One year, I began splurging on collectors’ edition video games — I was obsessed with the steel book game cases and statues. That same year, a few of my buddies and I were going to Comic Con, but one friend, who was dealing with depression, didn’t make a lot of money and couldn’t go, so I bought him a four-day ticket. It burned a hole in my wallet, but having him there with us and seeing him happy was good enough for me
But I learned to take a step back and not buy things I couldn’t afford.”
13. “My biggest regret is not getting it in writing that my parents withdrew money from my savings account when I was a teenager. My family was going through hard times and needed money to make ends meet for a bit, so they decided the best course of action was to withdraw money from my custodial account.”
14. “Loaning money to a family member when they were in tough situations. It happened repeatedly; the debt piled up and burned through my savings. When they got back on their feet, and I asked them about paying me back, they would always say ‘soon.'”
“Years later, I found myself in a tough situation, so they gave me a loan. Shortly after they gave me the money, they wanted to know how I planned on paying them back. When I mentioned that they owed me 10x the amount I owed them, they went to another family member and made a big deal out of it. I became the villain of the family and eventually paid them half of what I owed and cut ties.
Lesson learned: Don’t loan folks money without planning how you’ll get it back — and certainly don’t loan it out multiple times. Trying to be a nice guy burned me, and I’ve never recovered.”
15. “A few years back, I took out a $34k loan to buy a Michael Jordan rookie card in mint condition. This was at the height of The Last Dance hype, and I didn’t want to miss the chance to own a sports card I’ve wanted since I was a kid.”
“As with all markets, there are ebbs and flows, and unfortunately, I bought the card when it peaked in value. Now you can buy three of them in the exact same condition for the price I spent on one.
I learned nothing goes up forever, and if the value of something is setting record highs, it’s probably not a great time to purchase. Here’s my obligatory ‘timing the market is a fool’s game’ disclaimer: I believe overspending at the peak of the hype taught me patience and a better way to analyze trends going forward.”
16. “I spent $100k to get a commercial helicopter pilot’s license before realizing that a pilot’s life wasn’t very fun — fixed-term contract work, traveling around the country searching for a job, low pay, etc. I wouldn’t have ever been able to buy a house, build a relationship, or raise kids the way I wanted.”
17. “Instead of starting my second year of college, I decided to drain my bank account to buy my (now-ex) fiancé a car. He swore he’d pay me back and that he needed the money to buy the car before someone else did.”
“He only ever paid me back $200, and our relationship ended a few months after the car was purchased. I nearly ended up on the streets, had to put off college for a few years, and eventually filed a restraining order against him. It’s been almost 17 years, and I still regret every second of that relationship.
My advice is don’t let relationships sabotage your security and independence, and don’t be dumb with your money like I was.”
18. “Gambling. You can’t outgamble your losses.”
“Losing is not the problem with gambling; if you lost every time, you wouldn’t gamble anymore. Winning is the real problem.
The more you win, the more you increase your stakes. You win some, you lose some — no big deal. I went to a casino once with $2 and came out with over $500; the next day, I went in with $150 and ended up over $300 in debt.
It’s a brutal cycle where the money you make will not be enough to make long-term changes in your life, and you’ll lose it in the next round anyway.
Meanwhile, your brain gets so hooked on it that you start making illogical financial decisions in your daily life — even when the decisions are unrelated to gambling. You’ll start buying expensive stuff for your partner because you either feel bad about losing the same amount of money last night or because you feel confident that you can make more money if you win tonight.”
19. “When I was in the third grade, one of my friend’s neighbors’ was having an estate sale, so my friend had the idea to set up a lemonade stand and sell lemonade to the estate sale shoppers. He told me we would pay for the supplies and split our profits in half.”
Did any of these financial mistakes surprise you? Have you ever made a huge financial mistake? What did you learn from it? Let us know in the comments! (Or if you prefer to stay anonymous, you can use this Google Form).
Note: Some responses have been edited for length and/or clarity.
