Andrew Huff / October 24, 2010 10:28 PM

Blatantly stolen from this Reddit thread.

Back in the days of Mac System 7, you could set up things to open automatically at start-up. When I worked the photo desk at the school newspaper, I decided one night to customize the look look and feel of the OS, and ended up installing a plugin and an extension that conflicted with each other. When I restarted to get them working, the conflict essentially killed the computer. The school had to hire some serious Mac technician to hack into it and bring it back to life. I have no idea how much it cost, but I'm sure it was enough that I probably should've been fired.

lady fingers / October 24, 2010 11:36 PM

Hands down- Harrington College of Design- at this point, $60,000+ for two semesters, non-transferable credit, and an 18.25% interest rate that cannot be touched. le sigh.

jjj / October 25, 2010 9:27 AM

Compared to Lady Fingers, this is nothing, but I few years ago I bought an embroidery machine in the $1,000 range that I never once used. After a year I decided that I needed the money more than a big piece of equipment that I never used. So I sold it -- but at a tiny fraction of what I paid for it.

Pam / October 25, 2010 10:24 AM

Invisalign. $3000 out of my own pocket and it made my teeth worse. That or grad school.

R / October 25, 2010 2:05 PM

I overstuffed (and broke) my mom's washing machine, which was ancient and resulted in a month of hauling laundry to the laundromat while we waited for a part to arrive. She was pissed!

oio / October 25, 2010 2:21 PM

While looking under a pile of paper at my desk at a job I held many years ago, I found a $4,000 order for a product line that was suffering from weak sales. The order was six months old; I nervously called the customer to assure them that they'd get their product soon (after I planned to rush it through our supply channels), but was told that too much time had passed and they weren't interested anymore.

I walked the paperwork over to the shredder and quietly put the matter behind me.

radioactive_piano / October 25, 2010 2:40 PM

Dating my college boyfriend. Not only did he live two states away (a six hour drive), he didn't have a car, so I was the one to always go to him. He also didn't have a job, so I was the one who usually paid for things.

And he didn't have any business driving my car the night I wasn't feeling so well -- he totaled it by driving it right into the guardrail.

Meems / October 25, 2010 2:46 PM

I paid for my boss's cell phone payment with my credit card in which he paid me back right away. Months later I realized the company was still using my card and it was up to about $1200. I got some back, but the dude ignored me. Lessons - check your statement and don't help out acquaintences monetarily.

charlie / October 25, 2010 3:04 PM

Not staying on top of my tax situation when I first became an independent contractor. To anyone reading this who is new to that way of employment...PAY YOUR ESTIMATED TAXES. I thought I would just, ya know, take care of it when the money started rolling in!

Bad move.

JP / October 25, 2010 3:38 PM

I lost 400 Euros, which was about $800 in USD, when I was pickpocketed in the RER station at Charles de Gualle airport. I hadn't even officially reached Paris yet, and had literally just gotten off the plane about twenty minutes earlier. My wallet was stuffed into the outside zip pocket of my backback, I didn't even know it was missing until I sat down on the train and put my bag in my lap - and noticed that ht had been unzipped. The worst part was that half of that money belonged to my travel companion. Boy did I feel stupid. Now I wear those secret stash wallets whenever I travel, and haven't been pickpocketed since.

AndyM / October 25, 2010 3:42 PM

Applying for and receiving multiple credit cards when I was an undergrad. I will never know how much this cost me financially, but I'm sure the interest was extensive-- much of that debt stayed with me through my 20s. I'm now 100% debt free and take great pleasure in paying off my credit card each and every month.

dragonslayer / October 25, 2010 7:32 PM

This condo. Paper losses are $120K so far. Will probably take 10 years to recover unless I mail the keys back to the bank and destroy my credit.

paul / October 26, 2010 11:29 AM

While I've made a few business decisions that caused me to not make money, the only bad one that cost me money had to do with taxes - not paying for a year is like going to a loan shark - you'll wind up paying more than twice what you owe.

That and not paying off that pizza I put on Visa way back in college. I'm still paying for that.

Cinnamon / October 26, 2010 5:57 PM

Moving to New Mexico to be with a boy I no longer really liked but was too chicken to break up with. Hugely stupid, set me back quite a bit of money, but the hit to my self-esteem carries through to today.

Kelly / October 26, 2010 9:17 PM

I was on a business trip and went to get a rental car at the airport......only to discover my license was expired. I flew back home on my own dime, went to the DMV, then flew back to Nebraska (which somehow made it worse), rented a car, and finished out the trip. I'm not smart.

Conor and Viola / October 26, 2010 10:44 PM

Using a home depot credit card to upgrade the kitchen then being too scared to ask relatives to help pay off the $11,000 balance. Interest was approaching 21%. Chase paid the balance, now we owe them $470 per month for the next 25 years.

mom / October 27, 2010 10:38 AM

my first marriage.