Nothing stings quite as much as losing your hard-earned money, especially when you only have yourself to blame. We asked people to share the most costly mishap they've ever experienced. Sometimes they got duped, conned, or haggled into giving up too much dough. Sometimes they lost a bucketload out of plain old carelessness. Either way, they sure wish they could get a refund on these dumb mistakes that ended up costing them a fortune.
35. It's the thought that counts.
I went to Spain on a school trip when I was a junior in high school. One day on the trip we sailed to Morocco for the day. I was always told that Morocco had really nice rugs so I thought I would surprise my mom with a really nice rug. So we go into this room that was really sketchy with this Moroccan guy. Because I was looking at two different rugs so he brought me into the room to haggle with him. So he was writing down numbers and I returned with lower numbers. You know the haggling game. So at this point I'm 16 in this creepy room with this creepy guy so I'm getting a little nervous. In my flustered state I forget that 1 euro is about 2 dollars - I thought it was the opposite. So the final number we got to was about 400 euro so it is about an 800 dollar rug. I was all excited, until my dad found out how much I spent on a rug and almost flew out to bring me back home. So the entire trip everybody is making sure my rug is safe and always with us because I would be devastated if I lost it. So I come back home and my family is furious and demands to see the rug I bought. I finally open the package (it was wrapped up and I'd never opened it yet) and it was the WRONG rug!! It was this ugly brown rug. Nothing what I wanted. Biggest most expensive purchase ever.
34. A direct hit to the wallet.
When driving, figure out where you're going beforehand. Because if you look down at directions, you might hit a car and cause almost $7,000 worth of damage. I was headed to a gym I'd never been to before. I glanced down at my directions on the passenger seat. Quick glance, but in that time, traffic stopped suddenly (for a pedestrian darting across unexpectedly) and I was about to hit the car in front of me. I braked, I swerved, but I still hit him good. No one was hurt, but both cars needed a tow. Once the damage to my car was assessed at the shop, it came to the tune of $6,900 and change. Not to mention what it ended up costing the other guy.
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33. He fenced himself into a huge loss.
I paid several thousand dollars to have my back yard fenced in.
Two months after the job was complete and paid for, a neighbor complained that the fencing was about 2 inches onto his property and that it had to be removed, even though the fencing contractor said it had been done strictly according to a survey he had procured.
Turned out the neighbor was correct. By the time it was determined, the fencing contractor had gone out of business so I had no recourse whatsoever.
32. Buyer beware.
I made a real doozy. When I was young, I was in a bit of a rush to buy myself a car. I had a nice little nest egg of $20,000 put aside just for this purchase. I did a bunch of private inspections around my area, but I just couldn't find one I wanted.
I finally stumbled across the perfect car - great mileage (all country driving), full service history and in excellent condition. The only problem? The buyer was on the other side of the country. I decided to contact the dude and organise the purchase. After the money transfered, the ad disappeared and so did the car owner.
I just have no idea what was going through my head back then. It has been 5 years and they never caught the fraudster and I never got my 20k back.
31. Rookie mistake.
Had a part time job as a teenager at a Yamaha dealership that sold dirt bikes, atv's, motorcycles. I was told one day to deliver a Raptor to some address. Well, I loaded the atv up on the trailer and took off in the truck down the road. I noticed that the truck was low on gas so I pulled over and filled her up.. I made it about 1.5 miles down the road and the truck started running funny and eventually cut off. I had put gasoline in a diesel truck. I was fired about 4 days later.
30. Mid-life crisis leads to lifelong debt.
I was going through a bad time during my life and thought buying a new sports car, a 2007 Porsche Boxster to be specific, would solve my internal issues. It didn't and I was stuck with a debt. It was sweet to drive and I loved the looks it got, but it did little to resolve my actual problems. I paid it off and sold it 3 years later for a net $30K loss. I would have been better off spending the money on therapy.
Image by Pexels from Pixabay
29. Always leave a spotter.
I was travelling across the States with my friends and 6 days in we got to Miami. We were in Wet Willies and met a couple girls and we decided, at 3AM, it was a good idea to go skinny dipping. We all got naked and ran into the sea, leaving EVERYTHING on the beach. We got out of the sea after fooling around for a while and someone had stolen all our stuff. They took everything. I lost my wallet (with $300 in it), my iPhone, my passport and not to mention ALL of my clothes. And then, we all had to run back to our hostel naked which was a good mile away.
28. Salt on the wound.
When I was 18 my mother was killed by a reckless driver who was super wealthy. I had no supervision and no one to advise me in what to do (no dad, no relatives within 700 miles). I didn't "lawyer-up," and I took the first offer Statefarm offered - 100k. I now know that most insurers carry 1m wrongful death coverage. What's worse is, I blew that 100k within 8 months.
27. A crash course in getting conned.
When I was 18 I played in a metal band with some 25-year-old dudes that had just finished a tour. I thought I was there because I was a good drummer. Being so young and naive I never stopped to think why these guys never had jobs.
One day they asked me if I could pay for a new album. I said sure thinking that I would be on the road with them making money. I payed around $5,000 thinking I was going to be in a touring band. Well I was promptly kicked out once the tour was announced and they got another drummer. They were just using me as a mark. From that point forward I refused to contribute anything over my equal share to any band I was in.
I did have the last laugh though. I ended up working at a club they were doing a showcase for labels at around a year later. I had the sound guy run one guitar through a half second delay making them sound out of sync the whole time. Pretty much muted the bass, and made the drum triggers sound like tupperware.
26. Got locked out of a great deal.
Back in the 90s I was renting a really nice 3 bedroom, 3 story house on a hill in Northern California. The owners wanted to sell it to me for $189k, and they would finance it for me. The mortgage would have only been an additional $200/mo, but I declined as I "didn't want to get locked into a house."
They sold it to a real estate investor, and he slowly raised my rent every year for the next 7 years. In the end I was paying $1,800/mo for rent.
Then the real estate market went nuts and the value of the house shot up to nearly $700k. I lost my job and moved to CO for work. Had I lived there, I could have sold the house and would have made enough of a profit to buy a house in CO outright.
I did the math at some point, and all said and done I lost out on something like $500k due to profits and lost rent. Stupid, stupid, stupid. It took me another 20 years before I was able to afford to buy a house.
25. Missed the boat.
On a cruise with my wife, we messed up by thinking our cruise ship left at 4:30 instead of 2:30 and subsequently getting left in a foreign country. Spent about $1000 and 32 hours getting back to the ship at the next port. To be fair, an employee on the ship told us 4:30, and we believed him because we docked instead of tethered and so we weren't surprised the time changed. But watching the ship sail away from us was fun.
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24. A refund let-down.
I thought I was going to get a tax refund of about $3.5K, so a month before tax time I dropped 3 grand on a new PC, using my credit card. I failed to realise that since I'd started a new, higher-paying job that financial year, I was in a higher tax bracket than previous years. My refund was barely $600.
23. They were probably so glad to hear from you.
I was with a cell phone company that had great rates. $18 for unlimited everything, including international calling. I called my parents in the States multiple times per week and spoke for 30 minutes each time.
Turns out I had been using the wrong dialing code, which means I had been using a different companies network. It cost me $500+ over 2 months.
22. He couldn't guard against that.
My second year as a lifeguard for my local parks district, I was instructed on how to change hair catches and rid the air in the tanks of the pump house. Well, one day I mismatched the order in which to shut the valves off when filling the reservoir, and created what is called a "water hammer," a burst of air which carries a backwash up through pipes.
I thought it was normal cause the pumphouse had been there since the early '50s so I didn't make anything of it until I looked down the hill by the local library parking lot. The entire place was flooded. The water hammer found a rusted water main below the library parking lot and burst through the pavement.
The maintenance men said it cost the city over $800,000 to fix the main and keep the library from flooding and ruining the books. Thankfully it was an accident and not malicious or else I'd be living in said pump house.
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21. A chemical cataclysm.
I'm a chemist and was working on a reaction with a new palladium catalyst that we had just ordered. Since I was a stupid undergrad I didn't really make the connection that I didn't need to put in equal amounts (stoichiometric equivalents for the chemistry inclined) of the catalyst. I weighed out 200 grams of the catalyst and put it in the reaction. I mentioned to my boss later that day that we'd need to order more because I had used up almost all of it already. It was at that point that he mentioned that it had cost ~$15K for the 250g bottle and that I should have been using about 3 miligrams and not 200 grams. Not only was it very expensive though - it had taken over a year to come in after they had ordered it.
I was very lucky that I didn't get fired and that we were okay to use the remaining 50 grams for the next few years.
20. A real estate rip-off.
My wife and I bought a piece of land on which we had planned to build a house. We invested about 15 thousand dollars putting in a driveway, drawing up plans for a house, and general tests on the land. Come to find out the guy who sold us the land had staged a whole fake closing. Apparently he just wanted us to improve the land so he could sell it for more money. He actually had the gall to tell that to my face. My wife and I had no claim to the land. We contacted the authorities about it but they couldn't punish him for much, and we were left without any repayment or land. In our years since we've been far more careful, but we were able to eventually build our dream home, just 8 years later.
19. At least you passed the exam.
I was attending a school that did a drawing for free housing each year. It was a big production with prizes given out throughout the night with the big prize of free housing for a year (about $5000) given out at the end. I stayed for most of the night but decided to study instead of stick around for the drawing. Guess who was called out first? Me, except there was one problem: you had to be present to win. They gave the free housing to someone else.
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18. Cough up some change.
When I was a kid, my little brother got a flu-like illness and was getting loads of attention from my parents and got to miss a week of school. I was jealous, so I cuddled up to him to try and get sick. A few days later the school holidays started and I had failed (or so I thought).
A day into the holidays, I got sick too, and even though it was the holidays I was missing out on, I enjoyed the parental attention. Then that night, I felt really cold no matter how many blankets I had. Turns out I had a really high fever and pneumonia.
Cue chest X-rays, IV lines, antibiotics, a hospital stay and my holidays eaten up by the treatment and recovery period. Must have cost my parents thousands in medical bills, just because I wanted attention.
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17. Las Vegas means lost wages.
I was in Vegas with my girlfriend just about to head home. She went to the bathroom and as I walked past a row of slots and figured I'd give them a try. I put in my $100 with the plan to play $20 and cash out if I didn't win. When I put in the $100, the machine clicked once, and showed just 1 credit. I thought the machine was busted until I looked around and noticed that I was in the high roller slots area. It was $100 a play slot machine. Oh no! Well, nothing left to do but pull the slot and hope for the best. Of course, I lost. Later, when I we were driving home, I told her what happened. She asked me, "Why didn't you just cash out instead of playing it?" Ugh.
16. Living the dream.
My mistake was going to college at a time when I wasn't ready. Coming out of high school, I wanted to live the dream of going to college, then grad school, then get a decent job somewhere. However, I quickly found out that I wasn't ready. I couldn't focus on school. I treated partying like it was the priority and school came second. Somehow ended up making it through but with no chance of grad school. Major is essentially worthless, there's no market for it in itself. $160,000 of student loan debt is a lot of money when you make $10 an hour.
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15. There's no five second rule in hospitals.
So in the middle of the night the entire staff of the Cardiovascular Operating Room (Open-heart surgery) gets paged in because this one guy was tanking fast. Turns out that his heart was just totaled and he needed a transplant, but our hospital wasn't qualified to do transplants and we didn't have a donor heart. Cue technology. We did have a device similar to an artificial heart that could sustain the guy for a few days until we could get him to a hospital with more resources. The nurse goes to open the device to give to the surgeon, and accidentally touches a sterile part with her bare hand. Now the entire thing is considered contaminated, and they have to go open another one. They cost about $100,000 a piece, and the contaminated one just had to be thrown away.
Image by StockSnap from Pixabay
14. Should have sent it priority.
Not me, but a close friend at my accounting firm decided to break the "don't use non-encrypted flash drives" rule and copied all of the payroll information for the company I work for to his personal flash drive to take it home and work on it. Then instead of driving 30 minutes back to the office to upload the data, he decided to put it in an regular envelope and mail it back to the office. All that made it back to the office was an empty envelope with a hole that the flash drive ripped out of. The company had to buy every employee, about 2000 at the time, a year's worth of premium identity theft protection at $30 bucks a month. That equaled $720,000 all because one guy was too lazy to drive 30 minutes.
13. Total expense of the heart.
My first marriage. Was in the navy and got married. Shortly after, I reenlisted and got about 60,000, half up front. A week later went on a 3 month patrol. Came back and it was all gone. Her excuse was she was pregnant and had a miscarriage. Went to the hospital for stomach pains. Found out. They removed it for her and Tricare didn't cover it so it cost us 17,000. My dumb ass never bothered to check it out. I was just so upset that my first child didn't survive. She also stopped paying our bills so I spent a lot of my shore time playing catch up. Would get about 5000 every year for the rest of the reenlistment bonus to pay bills, but everytime I would go out so sea I would come to her with fancy purses and bedroom/living room furniture all on credit, and all the money gone. After the 4th patrol I couldn't handle it anymore and kicked her out. Prepared for the divorce and did all sorts of financial research to try to get out of paying her money. The dork at Navy Legal said I would be required to pay a third of my base pay (about 900 a month) to her for 2 years, so roughly $20,000. Found out all her lies. There was no miscarriage, just ridiculous expenses. Like waking up one morning and deciding she wants to see her mom. Buying a plane ticket for that day for about $2,000. Spend a few thousand while there for a week. A week later visiting her grandma so same deal. Marriage didn't last 2 years, but including everything she cost me well over $100,000.
Photo by Katie McNaught from Pexels
12. A pricey lesson learned.
Getting a DUI. On top of it being incredibly stupid, reckless, and dangerous... it ended up costing me $20,000 before it was done.
If there's a silver lining, it's that first and foremost, nobody was hurt. I was simply pulled over by an observant police officer. And second, it woke me up to the fact that I'm the kind of person who just shouldn't drink alcohol.
Things are much better now.
11. A plumber would have charged less.
There was a leak from my bathroom upstairs to the kitchen right underneath it. Every time someone would shower, water would slowly begin to drip into the kitchen. I thought there was a leak somewhere in the drain pipe and I took the kitchen ceiling down looking for it. And this was an old home, so there was this cement type of plaster with metal latticework through it on top of wood slats. It took forever to expose the drain pipe... only to find out that the little knob thing on the shower faucet that you pull up to turn on the shower had broken and I just needed to replace that. That piece costs me $7. Then I had to completely replace my kitchen ceiling.
10. Student debt strikes again.
I had no idea it was even an option to take classes at community college for the first year or two and then transfer into a 4 year university. Had good grades and standardized test scores so I was under the impression that my only real choice was which university I wanted to attend the next year. Meanwhile my girlfriend went to community college for 2 years, transferred to the same university and got a degree that looks exactly like mine for somewhere in the ballpark of $10-20k cheaper.
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9. Plus whatever the socks cost.
Being lazy (or just being normal) and leaving my socks on the floor ended up costing me a ton of dough. My dog eats EVERYTHING. And he swallows everything whole, so if he gets ahold of something, even if you see it, it’s down his throat in 1 second.
Cost me $800 to remove a huge tube sock that he managed to scarf down like a snake.
Sad part is, this happened twice, so make that $1600.
8. Paying through the nose for a knick.
I rented a U-Haul to move from an apartment to a condo in the same town, and bumped one of the balconies in the alley behind the condos. Put a very small dent in the canopy part of the truck, and when we returned the truck they told us since we didn't get the insurance we would have to pay for the fix within 48 hours.
They said that it would cost $4800 to fix, and they refused to let me take it to a third party mechanic for a quote. Then they said that if we didn't pay within 48 hours, it would go to court where it would be doubled.
I wasn't too well off then, financially, and maybe too naive, but we decided to pay to avoid having it doubled. My wife was in tears at the counter as she gave them her credit card. I will never rent another truck from them again.
7. The package got lost in the mail.
I had a business partner and this dude was PARANOID like no other. Few friends, cash only, no banks, that whole mind set. He wanted me to pay him for a job by mailing him $10,000 cash once to avoid having to pay to have it wired or having to explain anything to the IRS. I'd done it before by vacuum sealing it to make it as flat as possible and hiding it in clothes or whatever in a box. This time, I got lazy and just vacuum sealed it then slid the thing into a big cardboard envelope thing. Some slick postal employee must have known what to look for, because what got delivered was a cardboard envelope slit open up the side with a few blank papers stuffed inside. $10,000 untraceable dollars gone forever. I still wonder what the postal employee did with that. Hopefully took their partner out for a nice dinner and gave their kids a good Christmas.
6. The snowball effect.
In college, was a manager at one of those student painting companies. I hired an experienced painter who turned out to be a complete liability. In the span of a week, he stole $100 cash and some valuable LP's out of a record collection, got into a fight with another painter, in a room with lots of hardwood, staining the hardwood, got paint drips all over a really nice dining room set, then uses paint remover to get them off, ruining the finish, un-plugged a deep freeze full of artisanal salmon jerky and forgot to plug it back in and knocked over an expensive, high end stereo, breaking it. He managed to cover this all up because there was all sorts of contracting work going on, and the owners were out of the house for most of the week.
But this was NOT the expensive mistake. I contact the student painting company in a panic and tell them that we need to put through some insurance claims for this guy. They tell me there's no way that's going to happen, and to stall the guy while they figure out what to do. I sense that I'm about to get screwed over, so I decide I'll file the insurance claims myself. I contact the insurer, explain the situation, and submit 5 insurance claims in total. This sucked, because the deductible for each claim is $250. It turns out that in actuality, the $250 was my share of the $5000 per claim deductible. So I just submitted claims with $25,000 worth of deductibles. The painting company freaks out and cancels the insurance claims, without giving a reason, giving the home owner grounds to sue them. He wins in court, and got all the damages covered, plus an additional settlement. I can't recall the exact amount because this was almost 20 years ago, but it was something like $175,000.
Whoops.
5. Back in the days of dial-up...
I first got the internet when I was around twelve or thirteen years old. When I bought my computer it came with a piece of software, which was basically a free ad-supported internet service called net zero. The genius that I am got it up and going in no time flat, and I must say I was pretty impressed with myself. Ad supported browser sure, but I could still play a bunch of games.
My mom was pretty afraid of the internet when it first came out. She had severe reservations about the whole thing, and it took a lot of convincing on my part to get the internet in the first place. One of her big rules was to never divulge any sort of personal information. I was pretty okay with that rule, didn't affect me too much at all.
When I got net zero up and going I had to enter in my address and all that in order to get it running. In order to maintain anonymity, I chose the location of a time share my grandma owned in Florida. This seemed like a genius idea at the time, and I must admit I felt pretty good about it. Little did I know.
Well, after running this stuff non stop for almost an entire month, I was reading some message boards and my error finally clicked in my head. I was dialing up long distance to Florida every time I logged on, I live in Canada, and long distance was very expensive back then.
When I realized what I had done, I almost threw up. I ended up telling my parents a few hours later while we were eating dinner. My mom got on the phone with the phone company. The total bill was $3200. She was livid. As much at the phone company as she was with me. She was upset that, after having been a customer for however many years, they didn't give her some sort of warning that a massive bill was being racked up in long distance charges.
She ended up negotiating the bill down to half, $1600. This was now my responsibility, my burden. My dad ended up getting me a job in a, I kid you not, box factory. Just a side note, working in a box factory was more physically demanding than I would ever have assumed. I ended up working an entire summer, ten hour shifts, four days a week, in order to pay back the debt.
Mind you, I made a lot more than $1600 which was appreciated when the school year came around, but I still consider this to be one of the biggest mistakes of my entire life.
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4. Midlife crisis costs big bucks.
I bought a cute little sports car. I paid $2k for it, from my lab partner. It was a high mileage car, but my god it was fun to drive... For the first 5 or 6 weeks I owned it.
Then it blew a coil pack.
Then it blew a crankshaft sensor.
Then another coil pack.
Then another.
Add in other miscellaneous engine components along the way, plus breaks, and a few ruptured break lines. I don't remember what it was at this point, but I remember spending all day removing a manifold to change some tiny, cheap little part that was essential to operations.
Except for the first instance I did all the work myself. No way I could afford the prices of a European car repair shop. Each time I bought a coil pack they were more expensive. Last one was about $300.
All in all in two years I dumped about $2500-3000 into a $2000 car. Lesson learned, though I wouldn't say all the money was a complete waste. Some of that $2.5-3k were the tools I still own now, and have come in handy since.
3. A coding mishap breaks the bank.
My first job out of college I worked as a developer at a huge retail company's IT department. My team only consisted of myself, a lead developer and my boss, who also chipped in with the coding. Given our small size and flexibility requirements, I guess my manager didn't feel the need to burden us with strict protocols or safety procedures for testing and production deployment, as he trusted we were wise and responsible enough to do the right thing.
Well one day when I had a small bug to fix on the website checkout page, I thought I could save some time cutting corners. It was an obvious fix, and only a single line javascript update. To spare you the details, let's just say I made a coding typo. That typo ended up breaking the javascript on the page, thus rendering the checkout button nonfunctional. It wasn't until almost noon the next day that one of the sales representatives noticed we hadn't received any online orders for almost 24 hours (if only one of the customers had called the problem in sooner.). By the time I discovered the checkout button wasn't working and corrected the error, the estimated loss of sales was placed at approximately $40,000.
In the end, I got a warning and my boss finally decided to implement a formal deployment procedure that involved management approval before any production server updates. I value it as a crucial lesson learned: there's no change too small to warrant testing because even the simplest thing I do is vulnerable to causing catastrophe.
2. This just keeps getting worse.
About 15 years ago I met a girl named Betty. We met online and got along well. Things moved along well, then she lost her apartment. I had room so asked her to move it. Mistake #1.
We're living together, I think we're both feeling ambivalent about the relationship but weren't ready to break up as that's rather unpleasant. I should add she didn't want to break up because I was paying the bills and she had no place to go and no money due to her truly impressive ability to lose jobs.
So we're going along and all of a sudden she gets sick. We're talking major surgery sick. She had no health insurance but I did through work. So what did I do, being the stand up guy that I am? I married her to get her on my health insurance so she could get better. Mistake #2
She had multiple surgeries and procedures etc., and of course couldn't work. I was lucky enough to have been given stock for birthday/Xmas gifts by my father and they'd gone way up. I was sick of apartment living and wanted out of the city and back to the burbs.
I cashed in all the stock and bought a small house for us to live in. She was getting better physically and began working in an office. We still weren't getting along but we weren't not getting along either.
She needed a car to get to and from work as hers was a piece of crap. Her credit was a mess so I co-signed a car loan thinking that she could afford it if things at the very least stayed where they were for her financially. Mistake #3
Some time goes by and I begin to suspect there's something funny going on with her and her boss. Lots of texts, talking too much about him, late meetings etc. The usual signs of a cheater, I suppose.
I call her on it and she says she wants a divorce. I didn't have any proof of said cheating at the time so she filed due to irreconcilable differences.
Needless to say, I got my butt kicked in the divorce. To make matters worse, she was chronically late on the car payments which killed my credit. I managed to keep the house, thank gawd. It did cost me though.
A few months after the divorce, I find out that she and her boss were living together and he'd left his family.
Long story short, the most expensive mistake I've made was getting married for the wrong reasons. If only there were credit for being a stand up guy and getting her through her illness.
1. Money to burn.
The biggest and most expensive mistake anyone can ever make is lighting that first cigarette.
