January 30, 2023 | Casey Pino

Regretful People Share The Most Expensive Mistake They've Ever Made

Albert Einstein once said that “A person who never made a mistake never tried anything new.” I must be good at trying new things, because I know I’ve made plenty of mistakes in my lifetime. Often, the biggest mistakes we make are the ones that end up teaching us the most. We went to the users of AskReddit to ask them, “What's the most expensive mistake you've ever made?”

There are some real doozies. From hundreds and thousands of dollars lost to hard lessons learned about the importance of always reading the fine print, people share the time that they wish that they had known then what they know now.

Take heart as you read these, knowing that you’re not the only one who has screwed things up. Like the great businessman Henry Ford once said, “Even a mistake may turn out to be the one thing necessary to a worthwhile achievement.”


Don't forget to check the comment section below the article for more interesting stories!

#25 Good Fences Make Good Neighbors?

I paid several thousand dollars to have the backyard 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.

Image result for fence neighbourSouth Coast Register

#24 Time To Buy A Watch

Freshman year of college I thought my final exam was at 11:30.

It was at 9:30.

The exam was 40% of my grade, so I failed. I lost my scholarship and had to pay to retake the class.


#23 If Only

Nuked a hard drive that had a bitcoin wallet with around 30 bitcoins on it, which would be worth around $120,000 today.

*Cries while looking at my bank account with only $27.03 in it.*


#22 How Do You Make That Mistake?

Grabbed the wrong briefcase from my office while I was rushing to the airport... It had a loaded Walther P99 in it. $5,000 fine from the TSA, but it was bumped down to $3,000 because I paid within 30 days. Really stupid of me to say the least.


#21 I Got A Bridge To Sell You

Not me, but my best mate made a doozy. He was in a bit of a rush to buy himself a car. He had a nice little nest egg of $20,000 put aside just for this purchase. He did a bunch of private inspections around our area, but he just couldn't find one he wanted.

He finally stumbled across the perfect car for him, 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. For whatever reason, my mate decided to contact the dude and organize the purchase. After the money transferred, the ad disappeared and so did the car owner.

I just have no idea what was going through my mates head, it has been 5 years and they never caught the fraudster and my friend never got his 20k back.

22-1525488345504.jpgDaily Mail

#20 An Honest Mistake

I had a part-time job as a teenager at a Yamaha dealership that sold dirt bikes, ATV's, and 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.


#19 Burn It Up

Lighting that first smoke. I've done the math. A pack a day habit puts you at 200 bucks a month, 2,400 a year. And I live pay-check to pay-check. Something is wrong with me.


#18 A Hard Lesson Learned

It was a bad time during my life and I thought that buying a new sports car 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.


#17 Did I Do That?

When I was welding I 1) screwed up a $65,000 door and 2) may or may not have blown a hole in a $1,000,000 + missile launching platform.

To elaborate: The $65,000 door was an EMP/RF and ballistic door. The damage happened when I was using a die grinder to clear a bit of solder in a tube that ran through the door for some electrical- the bit grabbed and twisted the tubing and ripped it out. No way to fix it other than scrapping the door.

The launch module - I was welding and on the job site, there's a jungle of welding leads running everywhere - close to 20 machines? Well, mine was set good but my buddies wasn't. He just raced his leads to a wrong machine and ended up cranking mine up way to hot while I was mid weld. I was able to fix said hole and patch it up with no defects or such.


#16 Wear The Retainer

Not wearing my retainer after getting braces removed. My grandparents paid for the massive amount of work that had to be done so I feel extra guilty. I joined the army right out of high school and stopped wearing my retainer. By the time I got a new one, my wisdom teeth came in sideways and screwed up all that work. If I had just worn it like I was supposed to, I wouldn't be pushing 30 and considering braces again.


#15 Eyes On The Road

I was driving down the street and a woman blew a kiss at me from a bus passing by. I leaned over to my friends to say "Hey guys! Did you just see that? She blew me a.." CRASH ... ran into the little Volkswagon Fox in front of me and then he rammed the Audi in front of him. That sucked. I totally destroyed the Volkswagon. The dude in the Audi was super mad, taking talking how that was the second time that week that he had been hit. The guy in the Volkswagon looked a bit shaken but was not injured. My Jeep had a bent license plate. Crazy the disparity between the damages to the cars.


#14 Hope You Took The Warranty

The week after I got my brand new laptop that I bought for $1400, I ran it over with my car... woo.


#13 An Expensive Swim

I was traveling across the States with my friends and 6 days in we got to Miami. We got under the influence in Wet Willies and met a couple girls and we decided, at 3 AM, 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 messing 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.

We all had to run back to our hostel naked which was a good mile away.


#12 Whoops

Not wearing a condom with an ex-girlfriend because she said the doctor said she was sterile.


#11 One Lousy Zero

I work in construction estimating, yesterday we noticed a typo in our excel quantities sheet, instead of pricing 7000 square feet of sidewalk we priced 70,000 square feet of sidewalk. That 1 extra zero will cost us $460,000.00.


#10 Nothing Is Free

That first credit card. That "free" money started a spending spree. Fourteen years later and I'm still trying to get out of that hole.


#9 That Backfired

I pretended to hurt my back when I was a kid in order to get out of going to school. So, mom takes me to the doctor, I get an x-ray taken, and as it turns out there was actually something wrong with my spine. Didn't hurt at all, but they put me in a torso brace for 6 months anyway.

Remember kids, if you're going to fake sick, just stick the thermometer under hot water instead.


#8 Read The Fine Print

About 10 years ago I got a part-time job that miraculously offered health insurance. Unfortunately, the paperwork they gave me when I started only listed the insurance rates for full-time employees, something like $60 a paycheck. I didn't even realize there would be a difference for me until I got my first paycheck and it totaled about $20. I called human resources in panic mode, certain that there must be some mistake, only to be informed that for the number of hours I was working, health insurance was $400 per paycheck. And no, I couldn't cancel my enrollment unless I had a "qualifying life event." I took home $20 paychecks for 4 months until open enrollment when I could finally cancel. Luckily I had another job at the time so I wasn't out on the street, but it certainly taught me a lesson about carefully reading paperwork.


#7 Ew.

I know a guy who paid $25 for a cockroach infested PS2


#6 That's An Expensive Plant

I accidentally left an Asiatic lily plant out in my apartment when I went to work. When I came home, I noticed my cat had chewed a bunch of leaves off of if, and possibly swallowed some. I immediately looked it up online and saw that lilies are extremely toxic to cats. They can cause kidney failure from ingesting only a small amount. I had to rush him to a 24-hour emergency vet, where he had to be treated with high volumes of fluid via IV for 48 hrs. My cat made it out alive and I couldn't have been happier he was ok, but the whole ordeal cost me close to $3,000.


#5 Money Just Floating Away

I was on a canoe trip down a river with a number of large rapids and I forget to make sure my backpack was closed and stuffed in the boat so if we flipped it wouldn't float away. Anyway, the other person in my boat said we shouldn't run it with gear but I said we'd be fine and he relented. We flip and my bag goes floating down the river with about $200 worth of gear in it. The worst part was that my wallet was in that bag with most of my id. Whoops.


#4 Sneaky Sneaky

I left money I got for selling my camper (thousands of dollars) in my car while I was unpacking. It was only unattended for a few minutes and I was only about 20 meters away from my car. But somehow, my tenant stole it. I can't prove it but I have him on video stealing much smaller amounts of money in my house, so there is no doubt in my mind it was him.


#3 One Lousy Line

1st real job out of college doing data processing for a print and mail shop, about 6 months after hire, I copied and pasted address data off by one row. We discovered the mistake after 10,000 booklets had been addressed and the whole lot had to be re-printed. An over $20,000 mistake.

I drafted a proposal for a new question and answer process before I was called into the owner's office. When he was done yelling and cussing at me I accepted responsibility for the simple error and explained how we could avoid the same and similar issues from occurring again.

He didn't fire me and I learned one of the most important lessons in my career: how to handle failure.


#2 Take The Insurance

I didn't get travel insurance for my trip home (I live abroad) for Christmas. My mother suddenly died on New Year's Eve. Was at home for an extra month and that scrimping on a few pounds cost me about £1000.

4-1525489310511.jpgProdigy Piano Studios

#1 Everything Stopped

Rendering every laptop in the company unusable for more than a day, in a place where a lot of people are paid on commision. I don't know how much productivity was lost dollar amount wise, but it was a lot.




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