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People Break Down The Most Expensive Mistakes They've Ever Made

red ferrari 458 italia parked beside white building

red ferrari 458 italia parked beside white building

Reddit user lugulaga asked: 'What is your most expensive mistake?'

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When COVID first got bad, and my job became WFH, I didn't know the extent of it and thought we'd only be out for a few weeks, so even though I moved home because there were fewer cases in my hometown, I didn't give up my apartment, thinking I'd be back soon.

At the same time, I decided to go back to school, so I was paying both tuition and rent for a place I wasn't living in. It took about six months for me to realize COVID wasn't short-lived, and I let my apartment go. I wish I had known that before.


It definitely could've been worse, but I still did lose a lot of money for no reason.

To date, this is the most expensive mistake I have ever made, and hopefully, it always will be.

Redditors are no stranger to expensive mistakes, and they are ready to share their own.

It all started when Redditor lugulaga asked:

"What is your most expensive mistake?"

Locked Out

"I moved in with the wrong people and lost 95% of my posessions. It's a long f**ked up story but basically they changed the locks while I was at work and I couldn't get to anything that proved I lived there and then they moved everything in a day with a moving service. I can't even track them down because they were using false names and were apparently subletting instead of owning and they used false names when they rented the property. It was the most f**ked I've ever been in my life."

"I haven't found hide nor hair of them since...I suspect they hauled off across the country..."

– nmeofst8

Buy For The Future

"Not buying a house when I was in the 3rd grade."

– LittleAmiDrummer

"Same. I saved my money for Ninja Turtles and Transformers. I should have be looking at the big picture."

– Smooth_Riker

"No joke, I had passed on buying a house a $45k because I thought "It will be fine I'll buy a house later." The same house is worth $200k+ now. It would be paid off by now if I had just gone through with it 😭"

– Looptydude

Didn't Last

"Selling my condo 8 years ago to move in with my now ex gf."

– Schumi_jr05

"I hear ya on that one"

– Ari2079

​Unnecessary?

"Student loans"

– skinnipig

"This is it. I, among many I’m guessing, got my job without the need of my degree. It might’ve helped. But it didn’t help worth the amount of debt I’m in."

– CDawgbmmrgr2

"I was working for over 15 years in ten different jobs before an employer went and verified my degree."

– IrateGuy

Hurricane Wife

"Marrying my wife."

"She's like tropical storm - came wild and wet, and when she left, she took the house and the car."

"I wish that was a joke, but wasn't."

– spenalzo666

"Same here. My ex was horrible with finances, ended up being in 5-digit credit card debt, filed for bankruptcy, etc.. She almost had her car repossessed after she spent $2,000 to get it fixed and had two payments left on it (seriously???)."

"After the divorce, I ended up with about 1/4 of my 401K, I (voluntarily) gave up the house (I was moving back home anyway). She continued to rack up charges on my credit card (it had a low limit anyway) even though she was no longer authorized."

"Luckily, here I am 10 years later and much better off financially."

– draggar

Throwing Away Money

"In 2009 (or so, can't remember the date, but sometime between 2008-2011) my buddy got really into Bitcoin."

"It was back when bitcoin cost like, $5 per coin."

"I didn't understand it, I still don't really understand it. But back then, I had no desire to learn about this thing that seemed like a fad/scam."

"He did, however, convince me to invest, if only to shut him up."

"So I threw $50 his way and told him to get me 9-10, and he set me up with the bitcoins, and put them on a USB for me. Which, again, is another thing I didn't really understand or care about."

"So I tossed that usb in a box and didn't give a sh*t about it."

"When I later moved, I was packing things, and came across the usb I had labeled with something stupid. I still didn't care about bitcoin, and offered it to the guys I was living with."

"I remember one of them saying "dude, are you sure, bitcoin is at 10$.""

"I truly didn't care enough to learn about bitcoin, or even what to do with the usb to get the bitcoins off of it (or whatever you do with it) to bother figuring out how to recoup my $50 so I shrugged, tossed it at him, and moved out."

"Queue... the years that followed when I learned that my apathy and laziness had me give away what could have been today, something like $350,000cad, or closer to $850,000 at it's peak."

"So, yeah."

"My biggest financial mistake was giving away that $50. Could have really used that $50 over the years."

– Clay_Puppington

Lost Keys

"I was a head housekeeper at a small but very popular niche hotel. And expensive. I lost the master set of keys that could access every room in the place. My boss was on a 2 week trip in Africa and couldn't be reached. I had to use the company card to get a locksmith to replace all the locks on the doors quickly, because at that point, I didn't know if the keys had been swiped or if I had left them somewhere by accident..can't really f**k around with that though. I'm not gonna be responsible for someone getting murdered because I was too cheap to fix my mistake. It cost a ton of money. Boss was irate, but didn't fire me."

"Two days later I cleaned out my purse to switch it. Found the keys had slipped into a hole I didn't know was there in the liner.... never told a f**kin soul till just now."

– Friendly_Afternoon19

That Company Sure Grew

"I'm in Finance. I bought 100 shares of a little company because it pissed me off that Blockbuster charged me $88 in late fees. With this I could watch them whenever I wanted for a flat fee each month and as a bonus, they actually mailed the DVD's to you in the mail...you didn't have to drive to town and go inside and rent them. I thought it was a cool idea. We didn't really have much money back then so when we budgeted poorly I sold them for a $2000 profit. Was kinda happy about too lol."

"Damn, Netflix....I sure could use that $700,000 I missed out on 🥲"

– Dad_Is_Mad

We'll Make You A Star!

"I don't know if this is still a thing, but back when I was a kid, there were these "talent agents" that would "hire you" because you had the looks/talent to be a star. This was just a scam for you to pay them a bunch of money ( i think it ended up costing my parents around a grand) for acting classes that weren't real classes and other random fees."

– Crazy_Stable1731

"I knew someone that did this. I was there when someone said, "if they think your kid is so talented why arent they paying you?""

"Obviously real celebrities need to have an agent, and pay them, but the look on the woman's face when that was asked was pretty telling that she hadn't realized she was being conned."

– PumpkinPieIsGreat

"I would have these people walk up to me and hand me a card literally every time I went to Astroworld when I was a teenager. In my head I was always like "sweet! Easy gig, free money!" But my dad always shot it down and said it was all just a scam and wouldn't let me pursue it. Stupid parents always being right..."

– SweetCosmicPope

Time To Move To Canada

"As a newly wed, my wife felt very strongly that we get adequate health insurance. We had some from my work but it wasn't enough. We got a $4k check for a tax return and started shopping.. we found an agent, asked for a good year policy and paid him $4k. We paid for a year in full."

"The moment the check clears, the new policy sends us a letter saying that everything we thought we were paying for was no longer covered because we had another (primary) policy and would only cover certain events when my other crappy policy reached the out-of-pocket maximum of like $10k.. I paid $4k extra and still didn't have affordable access to regular Dr visits or preventive care."

"This was American Family Insurance. Absolute scam artists."

– Firebolt164

Pretty Packaging

"Renovating my house before selling it. In the end, the renovations didn't increase the selling price a bit. Now the new owners have an amazing house and I don't have the money I was going to use to renovate my own."

"Renovate a house for yourself, not someone else."

– capilot

That Tracks

"I don't feel comfortable telling you the names of my kids"

– flaming_poop_chute

Yeah, there are few things less expensive than a child. Luckily, they're also a blessing, so it should even out!

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