Regretful People Reveal The Most Costly Mistakes They've Ever Made

Regretful People Reveal The Most Costly Mistakes They've Ever Made
Photo via Wikimedia Commons

We learn from mistakes, right? So they're worth making. Unless that mistake costs you your living wage...then maybe not. Maybe you were better off erring on the side of caution.

u/One_Car_Garage asked Reddit:

What is the most expensive mistake you have ever made?

Here were some of the answers.

Millennia Mistake


Bought a 40 year old house on 3 acres that was 3' above flood line of the century.

4 years later we had a 1000 year flood.

$160,000 so far to remodel. In cash cause didn't have flood insurance.


Water Water Water


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.


House Time


Dad passed away, I was given his house 2+ hours away while wife and I had a newborn and were working full time. Let lifelong friend move in for monthly rent and he actually helped fix up the house and keep it in good condition. His gf started staying the night once in a while at the house, then more often. Him and gf had falling out. He left and stopped paying rent as we discussed. I sent family over to check on the house... Someone's living there? I check on house that weekend. It's my friend's now ex-gf living there.

She asks for 1 week to move all her stuff out that I didn't even know was there. I had my new family in the car with me and was not prepared for having to remove someone and all their stuff so I said ok. I was to come back the following weekend when my schedule allowed and she would be gone. Well this final week let her have a full 30 days living at my house, and she had proof, so she was now a resident and needed a full legal eviction to get her out of my house.

When youre involved in an eviction, there's all sorts of help and organizations and websites for the person living at the house to get answers. For the "landlord" evicting the tennant, I found almost nil. Had to pay a crap ton of money and had to drive to the county courthouse 2+ hours away like 6-8 times over the next two months to get her out of my dad's house. During this time, I was not allowed to enter the house.

I set up cameras on the neighbor's property with their permission, attempting record damage to the house, parties, theft of my property still at the residence... Didn't get jack squat.

She did about 40k damage to the home, stole a lot of my dad's belongings that were hidden in the attic, and cost me an insane amount of time. Well, really I did this to myself by letting my "friend" move in. Took almost 2 full years of going across the state every weekend to work on the house. I guess I can pay more money to go after her for the damages to the house, but she was living off illegal means and state aid during this whole process and would never be able to pay me back.

One final kicker... The house was heated via fuel oil in Michigan, and we have cold winters. This bitch ran out of fuel oil in late December, and she didn't have $150 needed to get a fuel oil delivery (you have to order a minimum amount to get them to drive out to your house and put fuel oil in your tank). She used electric heaters and had several of them running all winter to compensate. Because she was on state aid or some crap, the company couldn't shut off her power in middle of winter, so she racked up an average of $1,700 a month in electric bills over the winter. When I went to put the power back in my name, I was told that I have to pay her $6,300 balance before the power could be restored. This was because I didn't set up some landlord program with the power company in the first place. This took another 3 months or so, and a couple hundred to a lawyer, to get straightened out.

Wew I feel better. I think I made this long as hell so no-one actually reads it. It's like I'm pissed at her and myself all over again. Anyways, house is fixed up and sold now - for less than half the profit we originally anticipated. Jesus I lost so much money.


Tuition Down The Drain


I earned a few academic scholarships out of high school but didn't know how to use them. I figured they would have been automatically applied but I didn't start college right away so my lack of understanding, preparation, and willingness to ask people in the know resulted in me losing a couple thousand dollars toward my education.




When I built my first gaming PC back in 2005 I spent $800+ on the CPU alone. It was probably something meant for workstations and serious multitasking, and I stupidly thought "more expensive = better!". I could have had the same performance for gaming with something in the $200-300 range most likely. About a year later I also spent ~$500 on a second video card to get SLI, which was a big scam novelty at the time. The performance increase was super negligible and a giant waste of money.

I will say though, seeing some of the other responses in here makes me feel slightly better about my mistake.


Trust Lessons


I once trusted a person who said they needed cash to go to Boston to see a sick relative. I gave him 80 bucks for a bus there and back.

He shows up driving with a friend of his. I then realized he was scamming me.

Confirmed the next day when his girlfriend called and said he was arrested and she needed money to go see him. She said that he said I was his only friend, blah blah blah. And she asked for $100 to be money ordered to her.

Blocked numbers. I only lost $80 but I learned a huge lesson in trust.


How Rude


Rented a U-Haul to move from appartment to condo (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 to 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.

F*CK U-HAUL!! They'll never get another penny from me, the rest of my life.

You Don't Even Work Here


Not my mistake but an employee of mine was mixing pigment with powder to create a certain color ( I used to be work in Rotomolding) and accidentally used the wrong powder costing us $2600. But it doesn't end there because unfortunately my brother (Floor Manager) decided to give him another shot since it was his first week on the job still and put him on the machines with him. A little backstory on the molds on the machines they are welded then coated with Teflon (expensive asf) so we can only use plastic scrapers on them to scrape the other excess plastic, well this guy ignored my brothers warning and used a metal scraper quite nearly stripping all of the teflon (cant mold something that has scratches all over it or it comes out fucked) Needless to say he cost us $5000+ in damages in one day, and fired on the spot this time.

*sidenote this employee was fully trained and warned about these potential mishaps before each shift and during.


A House Is Not A Home


My parents bought a victorian farmhouse a year or so before they divorced. They'd already renovated a couple of houses at this point (it was partly a hobby, and partly a way of saving money) so didn't think twice about it.

Day 1 they realise that the house is falling apart. The garage can't even be entered because it's being propped up with a bunch of junk the previous owners decided to 'include' with the property. There's a well which was offered to them as a feature of the house but in actuality it's dangerous and something is wrong with the water so they end up having to pay an expert to cap it and pave over the area. There were a bunch of other problems but I was a toddler at the time so I don't remember the stuff that didn't directly affect me.

Anyway, when they divorced my Dad signed the house over to my Mum so she didn't have to juggle househunting while raising me. It was meant to be a generous move but honestly accepting that house was the biggest financial mistake my Mum ever made. It took her 12 years to save enough to move out. Constant repairs. There were rooms we never even used because they were in such disrepair. Even when we sold it she ended up spending an extra few thousands because the surveyor found that the foundations were messed up or the drains were weird or something like that. I remember she cried when we moved out because she'd finally built the house she wanted and then she had to leave it behind.




It was my second try to get my driving license back in Spain.

Everything went well apparently. I was asked to park the car so I parked it in a huge space. It was in front of a garage door, so I thought "I'll move it backwards a bit". Little by little, I suddenly heard a huge thud. I hit the back car.

Funniest thing, that garage door was unused and I could've left the car there, and that was the end of the test. But of course, I failed.

Now, I don't know about other countries, but in Spain (at least my region) there's no tests in August, and this was right before that. So I had to keep going to driving lessons for a month, failed a 3rd time, until I passed at the 4th try, and in total I spent like 1000€ more than what I should.

I'll always remember this.


When you gotta go, you go.

That should be a mantra for getting rid of the toxic people in our lives.

Not every relationship is meant to last forever.

Some people don't know how to be friends.

They are awfully good at pretending though.

Be vigilant of the signs and red flags.

Toxic people are crafty.

And once you're free, never look back.

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