Thanks all. This is comforting! In good news, I may be able to fix this current situation, and even if I can’t it will be a decade before it even matters.
I bought a brand new car. Spilled milk to seats, made a huge ugly scratch to the paintwork and all the way to metal surface. I am too careless to take care of a valuable car. I sold it with painful losses and learned my lesson.
About a decade ago, my husband and I were both working and earning good money. Our boys were just out of college and starting out on their own. We decided it would be a good idea to each make one of our boys the beneficiary of our life insurance policy.
Two years later, my husband was deceased after two years of grindingly expensive medical treatments and a year of my not being able to work at all. I was left with no income, a stack of bills, no job, and no life insurance to help. I had asked my husband to change his policy several times during his illness, but he repeatedly told me I wouldn’t need it.
I survived, but only after downsizing the house, signing away my future earnings to pay for the medical bills, and no longer having any savings. I got another job, but have never made as much as I did prior to taking time off to care for my husband. I do own my little house outright now, but I still have payments on those medical debts. And no, in my family you don’t do bankruptcy, although that is probably exactly what I SHOULD have done.
Long story short? Keep your spouse as your life insurance beneficiary.
Wow. That’s terrible.
Hmmm…
When I changed health insurance carriers two years ago, the old one continued charging me. I didn’t notice because my wife’s supplemental insurance comes from that carrier, so I expected to see charges from them. I would have seen two charges, but it turned out that her supplemental was being paid through social security withholding when we’d specifically asked for it to not be paid that way.
The old carrier was willing to refund 12 months of premiums, but I’m still out the other 10 months.
After reading that, spilled milk in that little Toyota I bought and sold doesn’t feel so Earth shattering anymore.
Buying a house in 2007. Cost me $60,000 to sell.
Thanks for the kind thoughts, everyone.
In all honesty, I’m going to be ok, although it was pretty grim there for a while. I’ve had to scale down what my retirement is going to look like, but I’ve still got 10 more working years to save for it and I own my house free and clear.
I only shared my story because what we did looked like such a good idea to us when we did it. And we were so very very wrong about that. I’d hate to see someone else make that same decision and suffer similar consequences.
I didn’t start saving in earnest for retirement until I hit 45. I didn’t learn about index funds for another 15 years.
Did you buy a house?
My biggest mistake was not applying for a grant program in time, and I lost out on 10k.
What did you do?
I’d rather not go in to it, at least not until I get enough distance that the stupidity doesn’t hurt quite so bad.
I took my Star Wars action figures out of their original packaging and played with them when I was a kid.
In all seriousness, I got married to someone I never should have married.
It’s a grim story, but I have to ask – if your son got the life insurance, was he not able to help you?
In 1997, I was visiting the computer science dept at Stanford and a young graduate student gave a seminar talk on his idea for a new browser. I though at the time that I should have gone up to him and said something like, “Sergey, if you ever start a company based on this browser let me invest in it.” I thought to say it, but I didn’t. His advisor–a good friend of mine–did invest. I can only assume he made hundreds of millions on it. What would a $10K investment be worth. i can only speculate.
Marrying and divorcing Mrs. Plant (v.2.0).
I think that takes the cake. 
I quit a government job with automated pay raises and generous retirement pension because I was bored with it. I could probably own a home and retire about now if I’d stuck with it.
I let my business partner talk me in to investing some of the company money in to an investment that did not pay off. I swear on a stack of Bibles that he says the deal was we would get our money back for sure, we’d just have to wait 5 years. And if there was a profit for our share we’d get that too.
We got nothing back, not even the original investment. And he swore he would never have told me that is how the investment worked. Soon after we made the “investment” business soured and we were broke as hell. So we just borrowed and borrowed money and maxed out my credit and went un-paid while these jerkoffs just got to keep our “investment” scot-free.
Fuck.
I bought a collection of Magic: The gathering cards around 2001 for around $2000, all the cash I had in my savings, because I knew I could sell it piecemeal for at least that much, most likely more. I indeed sold the highlights to make my money back, and then kept the rest for my own collection.
In 2003, I did some speculating on other cards with the savings I had, feeling that there were some cards whose values were significantly depressed at the time and I could make a could profit holding on them for a year. I did, and sold everything I speculated on for at least 50% profit, which was good.
All those cards that I sold are worth ten to twenty (maybe more, I haven’t looked recently) as much now. Deciding to cash out of both of them instead of further speculating on their rise in price is the worst investment decision I ever made. And it was an investment decision: all the proceeds went to paying off student loan debt faster while maintaining emergency cash reserves. The interest I saved on those loans is paltry compared to what might have been.