25 Money Mistakes That Left People Broke, Bitter, And Regretful

Managing finances wisely is a skill many people learn the hard way. A recent Reddit thread asked, “What’s the worst financial decision you’ve ever made, and what did you learn from it?” The responses ranged from heartbreaking to eye-opening, offering cautionary tales for anyone looking to avoid similar pitfalls.

#1

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Do NOT, under any circumstances, loan money to a friend or co-sign any loans with them. It messes up your life for a long time when they do not pay their bills.

#2

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Got 100k from my moms life insurance and blew it within a few years. I was 19. And so dumb. And so depressed. With no guidance. I learned the importance of saving lol.

#3

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Spent $100k to get a commercial helicopter license and then realised the life of a heli pilot wasn’t good at all. Fixed term contract work, traveling around the country looking for work, low pay, couldn’t buy a house, build a relationship, have kids in the way I wanted.Took a desk job instead and took 12 years to pay the loan back. Never flew again. My young brain got swept away with the idea of being a helicopter pilot without thinking it through.

In the end it worked out, apart from loving the flight training and living on the airport I also met my now wife. So the way I see it is it cost $100k to meet my wife who is now the guiding light in my life.

#4

Image source: OldMastodon5363, Andrea Piacquadio

Buying pointless “things” that now are just clutter I want to get out of the house. Expensive life lesson.

#5

Instead of starting my second year of college, I decided to drain my bank account to buy my (now ex) fiance a car. He swore he’d pay me back and that he only needed my money so he could buy the car before it was bought by someone else.

I was only ever paid back $200, our relationship ended a few months after the car was purchased, I nearly ended up homeless, I had to put off college for a few years, and I ended up having to get a restraining order against him. It’s been nearly 17 years and I still regret every second of that whole relationship. Don’t ever let relationships sabotage your security and independence…and don’t be stupid with your money.

Image source: 2baverage

#6

Image source: Judge_Bredd3, Alexandros Athanasopoulos

I had a job with a startup where the owner gave me some unrealistic goals and told me if I hit them, he’d make it worth it to me. I had nothing better going on, so I said “f**k it, I’ll take that chance.” I was salaried, so only getting paid for my 40 hours, while working 60+ hours a week for about a year. I hit the goals though and he surprisingly followed through. He gave me a huge under the table bonus. More than I would’ve made if he’d just paid me the overtime.

What did I do with that money? He said I should buy a house, it’s enough for a down payment and interest rates were really low at the time. Instead I bought my dream car (a 1970 challenger someone had thrown a 440 and T56 transmission into). Don’t get me wrong, I love that car, but houses then literally cost half what they do now and I still kick myself every time I think about it.

#7

Image source: Ok-Let4626, Luan Cabral

I was in a cult for 3 decades. I learned that religion is stupid.

#8

Image source: DesiGirl89, Natalia Blauth

Paid $7,000 to a witch to have her cast spells to get my ex back.

#9

Image source: missfitz1, Clay Banks

I thought I was going to k*ll myself in 2021. I used credit cards like it was my last month on earth!

I am now paying interest on my s***idal ideation.

#10

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Fell for ‘Buy Now, Pay Later.’ Now I’m Paying Forever.

#11

I didn’t start saving for retirement until I was 40.
I also grew up in a religious cult that taught me I didn’t need to save because Jesus was gonna be back by the time I was 30.

Image source: ironicoutlook

#12

Image source: Aniwaya1, Alexander Mils

I’ve p*ssed a lot of money into my parents’ situation. I’ve come to the bitter realization that all their problems are the result of poor decisions and bad behavior, and no amount of money will ever dig them out of the hole they’re in.

#13

Image source: EnchantedClamCake, Mikael Kristenson

Going to a four-year university right after high school. I could’ve gotten my gen-eds done at community college for free and saved so much money before transferring to a 4-year. I was too worried about what other people like my parents, classmates, and guidance counselors thought of me. If I have kids of my own one day I’ll recommend they go to community college first.

#14

I bought a horse. What I learned from this was that I should buy another horse.

Image source: thegingerofficial

#15

Being born to poor parents. Just don’t do that.

Image source: anal_bratwurst

#16

Image source: BackgroundGrass429, Florian van Duyn

Bought a 200 year old house.
I guess I learned. The next one we bought is only 100 years old.

#17

Marrying the wrong person.

Don’t marry the wrong person.

Image source: leons_getting_larger

#18

Bought a brand new car. No one can afford a brand new car unless they just have tons and tons of money. The $400 a month payment was the worst thing in the world and by far the worst financial decision I ever made. I grew to hate that car.

Image source: agreeingstorm9

#19

Borrowed money to purchase a car. My wife and I were newly married and had started our first real jobs out of college. We purchased a car after 4 months of starting our jobs.

When we multiplied our payments times the number of months of the loan, we were horrified by how much that car was going to cost. This was made worse because she was a mathematician and I was an engineer.

We made double and triple payments to end the loan and swore to never again pay interest for anything. Except for a mortgage, we never have: no car loans, no credit card debt, no home equity loans, nothing.

Image source: Silly-Resist8306

#20

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Got a car loan at 10% when prime was 3%, Never trust the salesman. Claimed the 10% was just a place holder until the banks opened.

#21

Image source: coloringpad, Aakash Malik

I didn’t file the proper form when I surrendered my house before foreclosure in 2016. One. Form. Didn’t know, used an online tax service and that was that?

I was told by the collector I would never hear from them again. Oh, how wrong I was. See, the IRS thinks I owe taxes on the sale of the property, but I just handed over the property under the guise of washing my hands of the dire situation.

Last time I checked, the IRS wants over 100 grand. I got nothing for the house. Now I had to go to a CPA. My tax guy has delayed them, tried too casually to get a tax advocate to correct the problem. Almost 9 years later, they have kept every refund and I have this STILL hanging over our heads. The IRS has not waived a thing.

All because of one form.

Lost a house, lost all my money I put into the house, currently paying twice as much in rent as my previous house payments. Not a dime to spare. One. Form.

Shoulda. Coulda. Woulda.

#22

Image source: Old-Body5400, Ahmet Kurt

Move without securing a job first because I had a good amount saved up. It took me 6 months to find a job despite being in a high demand profession and with experience. The job market is tough af.
I had $22,000 saved up. Drained it all.

#23

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Buying a gym membership in January. Turns out motivation only lasts two weeks.

#24

Image source: Toxic_Zombie_361, Joyce Busola

Recently fell for a romance scam. Lost all my savings. I hate myself.

#25

Image source: No-Compote-2127, Wesley Tingey

Gambling. You can’t outgamble your losses.

Losing is not a problem in gambling, if u lost everytime you will not gamble anymore. Winning on the other hand is the problem.

The more u win, the more u increase your stakes. You lose some, win some. No big deal, I went to a casino once with 2 euros and came out with 500, the next day went in with 150 and ended up with -300 euros.

Its a brutal cycle where the money you make will not be enough to make long term changes in your life and you ll loose them anyway on the next round of gambling.

Meanwhile your brain gets so hooked on, that you make radical, illogical financial decisions on your daily life even if its not gambling. Like buying expensive stuff for your soulmate, cause u either feel bad losing the same ammount last night or feel confident that you can make more money if u won.