12 of the Most Expensive Mistakes People Have Made

Finance, stress and senior woman with bills holding payment, document and paper with anxiety. Banking, accounting and worried elderly female with pension, mortgage and insurance debt in retirement
AlexanderFord/istockphoto

Everyone makes mistakes. But have you ever made a mistake that actually cost you a ton of money? Those types of mistakes hit on a whole different level. We scoured Reddit to find the most expensive mistakes people have made, and we’re knocking on wood that none of these happen to us.

1. Sleeping on a Sale

House object and wooden blocks with question mark
takasuu/istockphoto
takasuu/istockphoto

“Wouldn’t budge from $62,500 for a downtown loft. The owner wanted 65k. Unit sold for $275,000 1 year later.” – u/EMH55

2. Kids Do the Darndest Things

kid using cell phone
andreswd/istockphoto
andreswd/istockphoto

“I was around 8 when I thought I discovered a cheat/glitch that gave me unlimited gold in a mobile game. It turns out I was just buying gold with money. I cost my family $800 that day.” – u/Badilol

3. Stocks Will Break Your Heart

Afro american woman using smart phone at home, watching stock charts. Close up of hands, unrecognizable person.
izusek/istockphoto
izusek/istockphoto

“I bought $500 of Netflix [stock] in 2012 and sold it at $750 like a year later because I didn’t think it would go anywhere. Had I held, it’d be about $10k today. At its peak in 2021 it would have been worth $20k.” – u/dougiebgood

4. Car Insurance Is Crucial

A young insurance agent examines the damaged car's front view on the roadside. He provides expert assistance to the mature woman involved in the accident, helping her fill out necessary forms to report the incident.
supersizer/istockphoto
supersizer/istockphoto

“Not paying my car insurance on time. Then proceeding to slide through an icy intersection and hit another car. No one got hurt, just my wallet. Almost $7,000.” – u/sews4dogs

5. Hindsight Is 20/20

Creative growing green candlestick forex chart and bitcoin on blurry background. Trade and finance concept. 3D Rendering
peshkov/istockphoto
peshkov/istockphoto

“A friend of mine was an early backer of Bitcoin. Tried to convince me to invest a $20K windfall I had into it. In 2013. I said no, crypto was dumb. Said friend now never has to work again.” – u/MrSuperFantastic

6. Risky Business

Real estate agents are discussing the terms of signing contracts, legal agreements, land purchases, mortgages and home rentals.
Wasan Tita/istockphoto
Wasan Tita/istockphoto

“Signed onto a mortgage with my ex when I was 21 because he “just needed a little signature, it’s not a big deal!” Spoiler alert….. it was a very big deal.” – u/noodlemom72

7. Ouch …

2014 Polaris RZR
Tamara Harding/istockphoto
Tamara Harding/istockphoto

“Didn’t get insurance on a Polaris Razor. Side-by-side off-roading vehicle. Had it for less than 3 weeks and someone stole it from my driveway Christmas night. Had taken out a loan for 5 years… Making the payment every month hurt knowing I didn’t have it anymore.

Only took it out once. 14k for the trailer and vehicle. Still hurts a decade later.” – u/lastone23

8. Did You Have Job Insurance?

stressed out man at work
valentinrussanov/istockphoto
valentinrussanov/istockphoto

“Made a calculation error at work during my first few months there which led to the firm undercharging ~$130k on a project…how I wasn’t fired/written up I’ll never know.” – u/zombiehitler_

9. Defrost Activated

A view of a door handle that leads to a walk-in fridge inside a restaurant kitchen.
Photography By Tonelson/istockphoto
Tonelson/istockphoto

“At my old job, I forgot to turn back on the freezer after cleaning it (I got pulled mid-clean to go do something else) so I didn’t notice. Neither did my three managers.

Over $10,000 in frozen product lost.” – u/suhryna

10. Like Taking Candy From a Baby

watch on a wooden floor
:tapui/istockphoto
:tapui/istockphoto

“When I was a kid, my dad had a driver. One day, the driver came to our house, saw little kid me, and told me that my dad needed a watch for work and asked me to get one from his closet. I gave his driver a random watch and the driver never came back.

I gave the driver my dad’s Patek.” – u/Fickle_Duck_4770

11. No Return on Investment There

house for sale
Feverpitched/istockphoto
Feverpitched/istockphoto

“Buying a $150k house as a young man, with a 30 yr mortgage. I paid my mortgage every month on time, made improvements, and wound up moving 7 years later. I sold for $10k under what I bought, and at closing I made $500. Banks are criminal…” – u/olson544

12. Get Your Calculator Out

tiny house being hauled
ablokhin/istockphoto
ablokhin/istockphoto

“Caused a car wreck that destroyed an entire tiny home and the rented truck I was hauling it with, to the tune of 13,000 for the truck, the 9,000 it had cost to transport the trailer that far and repair it from its first disaster, (it’s a long story), the 4,000 to clear the freeway, the 2,000 for the emergency movers, and whatever we could have sold the tiny home for.

$28,000 is the biggest, unless I cheat and count going to college.” – u/Excellent_Law6906

Author
Rachel Schneider

Rachel is a Michigan-based writer with a bachelor’s degree in Professional Writing and English. Throughout her career, she has dabbled in a variety of subject matter from finance and higher education to lifestyle pieces and food writing. She also enjoys writing stories based on social media trends. Find her on Instagram @rachel.schneider922