17 Things People Spent Big Money On That They're Kicking Themselves Over Looking Back

There's nothing worse than finally deciding to make a big purchase, only to realize you've made a HUGE mistake.

Woman using credit card on phone
Oscar Wong / Getty Images

Recently, Reddit user u/The_guy321 asked, "What is the biggest money mistake you have ever made?" Here are a few responses:

1."Becoming a doctor. At the end of the day, it’s just a job. It wasn’t worth flushing my 20s down the drain and accumulating a mountain of debt for this. I’m (finally) in a good spot in life now, but I don’t think the sacrifices I made to get here were worth it. Even from a less self-centered point of view, I don’t really do that much good for others with this job. Modern medicine is so much better at dragging out death than it is at improving life, and I’m tired of being a part of it."

u/LtDrowsy7788

2."I bought a vintage guitar from England (I’m in Canada) and had to get it shipped over the pond. Being a somewhat delicate item, I went for some pretty expensive shipping which was a lot, but not much compared to what I paid for the guitar. I wrote my address wrong, and the item was shipped to Canada, had an invalid address, was held at the depot for a couple of weeks, then shipped back to the guy in England. I had to cover a fee and once again get it shipped over the pond."

u/P0ster_Nutbag

3."Going to college right out of high school. College is great if you know why you're there, but not for someone who isn't yet sure."

College graduation ceremony
Nirat / Getty Images/iStockphoto

4."Timeshare. I went to the seminar for a three nights stay at a beach resort. They got me. There were phenomenal salesmen, but they lie out of their asses. We spent thousands over a few years, only used the timeshare once, and paid a lawyer to get us out of the contract (basically a mortgage). Now we’re free!"

u/jginapouchman

5."I bought a mobile home as a starter home. No one ever explained to me as a young adult the importance of investment and future planning. Mobile homes of course do not hold nor increase in value, so you never build equity. It's akin to renting, except you have to cover all your own repair costs, too. It's a terrible financial decision. Don't buy mobile homes kids. Just don't do it."

Mobile home community
Marje / Getty Images

6."Buying a boat...don't buy a boat."

u/Fainterepl

7."I agreed to take over my ex-girlfriend's bills so that she could pay off her debts. Five years and over $100,000 of my money later, she was in more debt than when we started and cheating on me. Don't ever do this, just make her be an adult or dump her ass. It's never worth it."

u/Stoneluthiery

8."Sold my signed Banksy prints for a couple of grand to fund a new kitchen. Saw the same prints a couple of years later selling for £80,000 ($97,848)."

u/RobotGoatBoy

9."I opened a credit card in college, bought something (I don't even remember what), and completely forgot about it. I never got a statement, three years later, I suddenly have collections agencies calling me nonstop over a $20 debt with hundreds in 'collection fees'. It took years to get my credit back to 'not shit' levels."

—u/Hured2001
Alexialex / Getty Images/iStockphoto

10."Five years ago I bought plane tickets for my ex to come and see me, and he canceled on me three days before saying his grandma was on her deathbed (she is currently still alive). I was 16 and I wasted three years' worth of savings."

u/mangotangy

11."Financing a used car and then leasing a new one. Never again! I bought my current car in like-new condition and paid in full with cash. I love never having to deal with car payments!"

u/JOEYMAMI2015

12."Lending my credit card to family."

u/Victor882

13."Not mine, but my dad's. He bought, like, $500 worth of collectible Star Trek dinner plates in the '80s thinking they'd be worth a ton of money in a few years. They're not."

u/Theareyj

14."Ages ago, I lost my job and waited way too long to sell my luxury car I could no longer afford. The job hunt took much longer than expected and then I sold the car for far less. It was really dumb. All totally good now, but it a good learning lesson."

Sports car
Johannes Schmoelz / Getty Images/EyeEm

15."One of those Bootcamp style gyms opened up within walking distance from our apartment. We wanted to get in shape and figured we'd check it out. It was run by a married couple who was really nice. Initial classes were very small but the exercise was great. The husband also did martial arts instruction so I was considering getting into that. They were doing a really reduced special to get a year membership, so I went for it and paid half upfront. A few weeks later, they asked for the remaining payment and I said 'Sure, why not?' A little bit after that they called and said, 'Sorry, but we opened the gym with a verbal agreement that we would be getting a large number of karate students and that fell through, so we have to shut down. We will get your money back once we get settled after we move back home.'"

"I foolishly had paid for all this but never had even gotten a written contract or whatever. They just ended up ghosting me and stopped replying to everything."

u/urchisilver

16."I bought a condo in July of 2007. The timing literally could not have been worse. I could have bought it for virtually half the price if I waited a year. I sold it just last year for less than I bought it (after inflation)."

u/wei_ping

17."Just this year, I started a retirement account. Nobody taught me about this shit. I'm 12 years into working. I could have had 12 years of gains, but instead got like $10 interest in my savings account. Why is money management not mandatory for high school graduation? I was taught nothing. I still know very little and trying to teach myself is like pulling teeth."

u/CheesyComestibles

Is there a big purchase you wish you could have saved yourself from? Tell me about it in the comments.