Anonymous wrote:Divorce.

The divorce or the marriage?

Divorce.

In 1999, I had a chance to invest and debated if SUNW or AAPL was a better investment. No prizes for guessing which one I picked

Private elementary school for my kids. Realizing now that I could have taken that $500k, invest it, and then buy their way into a college.

In 1997, some friends and I had a stock "club" where we pretended to put money in stocks and watched what they did. I had $2000 in pretend money invested in Apple, which was deep in the depths of its John Scully days at the time.

Had I put $2000 of real money in AAPL, it would be worth about $3 million today.

Oops.

Bought a condo in south Florida in 2005.

Being financially illiterate in my 20s and early 30s and not taking compound interest seriously.

Fooling around with call options under the advice of an old-style stock broker decades ago. Lost about $10K. Never again.

Getting married to the wrong person and subsequently divorcing. It continues to cost a huge amount of money.

Anonymous wrote:Held on to my company stock way too long out of stupid loyalty.

Oh, DH did this as well for one of his former employers, and now still getting paid in sh#% stock for his current employer. ugh.

Anonymous wrote:Stop investing in the market after the 2008 crash.

Ouch.

Anonymous wrote:Going to law school at the best one that accepted me T-15, instead of taking a near total tuition free ride at a respectable T-25 school.

Fortunately, I did the opposite—took a full ride at a T3 and took night classes while working instead of going deep into debt. My law school doesn't impress anyone in DC, but it was enough for me to get a good government job.

My biggest financial mistake was getting a Ph.D. It was "free," but the opportunity cost was huge because I was making grad student money instead of what I'd have been making as a practicing lawyer.

Anonymous wrote:I bought an expensive piece of art while manic. Saw the work of the artist hanging in a window at a gallery and wandered in off the street and bought the damn thing. It cost so much I ended up unable to make my credit card payments and my very sweet boyfriend (now my DH) took pity on me and just paid it off. I absolutely hate the darn thing now and let's just say it didn't appreciate, lol. I've looked into selling it and couldn't; it's worth nothing. Ugh.

I did this too. My wife and I saw an expensive (for us) piece of art, liked it, and bought it. Later on I realized that we probably paid too much for a "limited print" of something that probably had not that much resale value. I was happy to let my (now ex) wife have it in the divorce.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Going to law school at the best one that accepted me T-15, instead of taking a near total tuition free ride at a respectable T-25 school.

I did the same thing. Well, similar. I ignored a scholarship from Notre Dame and went to a school that was ranked lower because I wanted to move to that city. It all worked out, I loved my law school years, but it wasn't the best financial decision to just ignore the full scholarship offer.

This is insane. I could see turning down Notre Dame for a higher ranked law school, but to go to a lower ranked school and pay more just because it’s in the city you want to practice in makes zero sense. The Notre Dame degree travel well.

My husband did the same with Law School in the 90s (Harvard) and he had free tuition at Georgetown (ended up in DC as a DOJ honors attorney) It was hard to pay off 85K in debt in decent paying jobs, I can't imagine taking on more student loan debt. Luckily, I did not have college debt and no graduate degree so we were able to pay it off. Also, we bought a Marriott Timeshare about 15 years ago and that was the worst waste of money ever.

This is not a humblebrag just a brag.

Held on to my company stock way too long out of stupid loyalty.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Going to law school at the best one that accepted me T-15, instead of taking a near total tuition free ride at a respectable T-25 school.

I did the same thing. Well, similar. I ignored a scholarship from Notre Dame and went to a school that was ranked lower because I wanted to move to that city. It all worked out, I loved my law school years, but it wasn't the best financial decision to just ignore the full scholarship offer.

This is insane. I could see turning down Notre Dame for a higher ranked law school, but to go to a lower ranked school and pay more just because it’s in the city you want to practice in makes zero sense. The Notre Dame degree travel well.

My husband did the same with Law School in the 90s (Harvard) and he had free tuition at Georgetown (ended up in DC as a DOJ honors attorney) It was hard to pay off 85K in debt in decent paying jobs, I can't imagine taking on more student loan debt. Luckily, I did not have college debt and no graduate degree so we were able to pay it off. Also, we bought a Marriott Timeshare about 15 years ago and that was the worst waste of money ever.