Your Costliest Mistake?

What’s your costliest mistake, in terms of financial setback?

We signed up with an investment fund, primarily because my brother-in-law was selling it. It was a mistake and tanked. We didn’t lose all our money, but got back a lot less than we paid in. The only bright spot was that we took a capital loss on our taxes that year.

thinking that because I loved him, money didn’t matter. If he needed it to friggin pick his nose, i’d give it to him…boy is my credit fukked up and I have not seen my pc and a couple of thousand dollars since

Got a job at a company, and the hiring manager asked me in to his office to discuss the terms of employment. I looked at what I thought was a big salary and said “I don’t think there’s anything left to negotiate.”
If I’d just asked for a stock option, given that the stock went up 480% by the time my shares would have been vested, I could have excercised it and made somewhere between $50,000 to $150,000.

If we’re talking errors where I actually had to pay out money, rather than just not receive it, it’d be lending my credit card to my girlfriend “for emergencies.” That cost me $5,000.

Oh, and my wife and I made some really terrible tax decisions this year which will probably end up costing us at least $10,000, plus penalties…which is not so good, considering I’m unemployed.

Ugh, I’m going to have to stop thinking about these things, they’re too unpleasant.

Grad school in Creative Writing at Columbia. That got me buried under about 45 boxes of ziti. Not to mention credit card debt I accreted while I had only a work study job, had to pay rent, and was dealing with a vampire of a live-in girlfriend.

Wouldn’t have such a good job now, though, if I hadn’t done Columbia… even though I never did get the degree (the job came while I was All-But-Thesis, the degree wouldn’t have helped me, and the job was challenging and rewarding).

But still not something I like to think about. Hell, since I’m still paying for it, who needs guilt?

Getting married (in a beautiful but not cheap wedding) to a guy who would not get a job and then trying to divorce him. He fought the divorce (just to be a prick), filing the most ridiculous motions and so forth making the divorce cost almost twice what the wedding did and I’m still on the hook for both.

I hired a “friend” to build my deck. Only cost 2x the estimate and its not even close to what I wanted.

I hate my deck.

“Lending” two large to an ex-girlfriend to buy a car.

Same ex also ran up about $600 on a store credit card. Worst part about it was that she had called customer service and changed the mailing address from my apartment to hers. I didn’t find out until almost a year after when Mrs. Gaffer and I went to that particular department store and were attempting to buy something with my store credit card which I had proudly produced with the claim “You know, I’ve never even used this card!” One phone call to customer service later, I learned that not only was the card over the limit, but I hadn’t made a payment in 8 months!

Yep, she was one good-looking but expensive bitch.

Taking a friend’s hot tip on a stock and watching it promptly go from $14 to 5. Cost me about 30K. Keeerap.

I lost about $3000 on a “get-rich-quick” scheme I went in on with a friend. The plan was to go to government auctions and buy stuff for dirt cheap and then sell it again for a profit. Start small, take the profits from these items and parlay them into bigger purchases, which in turn could be sold for a big profit. Eventually we’d be able to buy foreclosed properties and be selling them. My friend had me go to the seminar with him, where people gave their glowing testomials about how easy the program was and how quickly they became rich. I was skeptical, but was foolishly convinced that we could do it, too. In the end all we wound up with was a bunch of old crap that we could hardly sell for what we paid for it, if that.

using credit cards for credit.

Not buying a temporary major medical policy to cover the 30-day transition between the insurance at the old job and the insurance kicking in on the new job, and then breaking my leg in a zillion places on Day 28. That one cost me several grand.

Never, ever, ever be without medical insurance, at least not if you are ethical enough to pay bills you incur while uninsured.

I cost a developer slightly more than $750,000, but I swear it wasn’t my fault. It was a honest mistake.

Dude…aren’t you gonna elaborate? $750 Large is quite a few Mistake Bucks.

Getting married.

Net result: me, one car worth approx $10,000
her, house, car, worldy goods worth approx $200,000

After I worked to support her through university

:frowning:

Never again, no way, no how

Engaging in an extramarital affair: Cost me everything and then the other woman dumped me.

Promise?

Letting the bank provide insurance coverage on my truck when we were plugging along one one income and decided that the money situation was “too tight” to pay regular premiums. :smack: :smack: :smack:

Going to an expensive private college for four years, when, unbeknownst to me, I qualified for FREE TUITION at any public university in Ohio. (It was through a relatively obscure scholarship program for the orphaned children of veterans.) By the time I figured this out and transferred, I was $27,000 in the hole.

The price of ignorance. :frowning:

I did two weeks of casual legal work around the end of last financial year, when I was still a student. I chose to do the work in early July 2002 instead of late June 2002.

If I did the work in June, the money I earned – some $1200 – would have been tax free, since my total assessable income for the year would have fallen below the taxable. Instead I did the work in July, which is part of the current financial year. I graduated and started full time work in January 2003, so now I’m well over the tax-free threshold.

It isn’t a big amount now, but when I was a dirt poor student, it sure would have been nice to get that juicy tax refund.