“What Is Your Most Expensive Mistake?”: 45 People Share Their Stories

Went to an Ivy League school for nursing school. Now I have $90k of debt, literally no one cares where you went to school, my peers who went to community college or state schools are doing the exact same job and buying houses.

Not caring for my teeth when young.

Started smoking at 14. On and of for decades, off for over a year now, but I must have spent enough to put a down payment on a house between the cigs and associated health issues. Don't start kids, not even one!

Not enrolling in my company’s retirement plan that offered 5% contribution match. Lost five years of free money.

Not taking diabetes seriously cost me the vision in my right eye.

My most recent was going to the doctor.

Went for a PAP smear. Asked 4 questions relating to my birth control and the vagina since I was seeing a gyno that day.

Received a $413 bill because the 4 questions I asked were "deemed outside the scope for the appointment". Over $100 per f*****g question.

Buying into shallow beauty habits. I cringe at the thought of how much money I spent on hair, nails, club outfits, accessories, etc. All cause I was a vulnerable teen convinced by my society that I wasn't beautiful enough and I needed to pay to get right. I can't imagine being rich and feeling that way with the ability to go further and get surgeries....sheesh....that's like an endless bill all cause society is in the business of making people feel like they're inherently flawed...

My father died in 2007 and left me and my sister $115k each. I used it to buy a new house.

I was 25 at the time. Didn't know s**t about the process to buy a home. So needless to say I bought something I couldn't afford. Then the market crashed in 2008. I lost the house and my inheritance.

I was more upset about blowing my fathers savings than losing the house. Lesson learned.

Taking out a $5,000 loan to help my Mom with her very very past due bills.
Long story short, she ends up missing bills again and not learning her lesson.

Losing my USB that had 50 Bitcoin on it. It was a prize for getting 2nd in a guitar hero contest hosted by the university I was attending.

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.

Marriage to a narcissist. They always think they are right. I had a house and stock portfolio. We get asked to join in on a property investment. I was in love/gullible.
He was self-employed. I quit my job to be a SAHM which I don’t regret but there went that career and retirement plan. Then came the market crash and the business he ran suffered a huge hit. If I had $50 I would try to make it last a week to feed the kids and us. If he had $50 he’d buy steak. Once he made a pile of money but instead of paying down debt, he bought his kid a BMW. His ventures were always huge things; couldn’t handle being an employee… feast or famine but he controlled all the money. Divorce was long and drawn out and cost a lot. I had to drive the new expensive car that we could never afford until the divorce was final. In the meantime, the water pump failed and I had no choice but to fix it. Stupidest car choice ever. I feel like I got reset back into my 20’s financially, buying my first new to me car a year ago. Can’t afford a house because of the current market. Will never hand over financial decisions to anyone else ever again.

Tried messing with stocks out of boredom during Covid. Ended up getting into options and getting myself in a hole.

Instead of accepting my losses, I continued to make more risky investments, if you can even call them that. Ended up losing about $20k or so over the course of 8 months. I was engaged when I started getting into this and got married about halfway through and did all of this without my now wife’s knowledge.

We decided to start looking into buying a house and I had to come clean prior to applying for loans, so that I didn’t cause some long-lasting damage to us financially. It was a rough conversation and we ended up moving in with my in-laws as we try to recoup my losses and buy a house down the road.

Was definitely a tough stretch of life. Contemplated suicide and thought my marriage would be over before it even started. Thankfully, my wife had enough forgiveness to let me make things right. We both have good jobs and it wasn’t really a life-altering mistake when all things are considered. In therapy now to deal with the mental and marital issues that arise throughout the process.

I strongly advise anyone in a similar situation to cut your losses and have the difficult conversations sooner rather than later.

Bought a house 50/50 with my brother in law. I was in university full time and working part time. So not a lot of extra time to keep track of the house stuff. First year ends, find out the join house account is over drawn by $3000, because they hadn't been putting their share in the account. I pay that off, then the end of my second year... 3 leans against the title in his name.... over $45,000. Try to sell house for 2 years... no one will touch it, I have now taken out all loans I can to keep the house... bankruptcy, foreclose, lose over $250,000 dollars on what it was valued over what we had paid for it, not including the $15,000 down payment, and the $20,000 of reno's I paid for.

Life lesson learned: never go into anything financial with family.

Agreeing to not having the septic tank inspected before closing on our home. It was pumped recently so it must be fine, right? Turns out it was actually in bad shape and needed to be fully replaced. Over $20,000.

Bachelor's in Anthropology, Minor in Music.

Second marriage. She spent a LOT of money without my knowledge, including my retirement account.
I’m 64 and will be working until I die.

Got in a fight while on an exchange program, ended up awaiting trial in jail for a year before being released. All loans and scholarships were cancelled.

Left my laptop on the front counter of my work while going into another room. We are in a major homeless area. Came back 15 minutes later and mine and the receptionists laptops were stolen.

Fairly decent laptop more than the actual equipment, lost 10 years of work- scripts and plays, databases, artwork, and hundreds upon hundreds of lesson plans.

I now back up to the cloud all the time.

Rushed into buying a car. Bought a salvaged vehicle that looked like it was in great shape. It drove fine, and it was exactly what I needed at the time. About a month in some frame damage was discovered that made it hard to steer, and there were NO F*****G AIRBAGS! I tried to turn around and sell it once I found out, but I couldn’t in good conscience sell an unsafe vehicle to anyone. So I pay $7K to install new airbags and have a few other things done. Once the car was safe, I felt like I could stick with it a little longer…then the transmission started leaking. I had grown attached to the car by this time, so I figured I’d at least get an estimate on fixing the leak, even if it meant dropping the transmission. Mechanic gave me a call moments after I dropped it off to tell me he was worried that if he dropped the transmission he wouldn’t be able to put my car back together, because the repairs on the car were so bad the transmission was essentially holding the whole front end together!! Sold it for scrap and basically lost $15K total on that terrible purchase.