What is the Worst Financial Decision/Mistake You Have Made?

Drinking. Between 19 and 28, I probably spent close to $50,000 on alcohol or alcohol influenced purchases. Luckily, I've always done fairly well financially, but I'd be way better off if I had never picked up the red solo cup to begin with. I'm fortunate to have quit and, after a couple of years, I'm loving all my budget surpluses.

When Elon Musk was looking like he was going off the deep end a couple of years ago I sold most of our Tesla stock. Cost me about $320K based upon what it is now worth. Fortunately, we did keep the 50 shares we bought at $19 (amount invested less than $1000) which are now worth $173K.

My problem usually, however, is that I tend to hold on to big name legacy corporation stocks which have gone out of favor; e.g., GE, Chevron and ExxonMobile. I need to pay more attention to what I am holding and be willing to cut my losses.

deja vu wrote:

Danny Bandana wrote:

I feel it helps being able to learn from others mistakes, plus misery loves company! :-)

What would you consider your worst financial mistake or choice that you have made in your life?

Hindsight is 20/20 but my late father invested his hard earned money in a farmer's Co-Op that went bankrupt and he lost close to $200,000.

I remember that one haunted him for many, many years.

I swear I just read this thread on bogleheads.

Ditto. I had to do a double take that I was not on bogleheads.

In 1994, I bought my first house for (what I thought was an astonishingly high) $72,400 with a small down payment. Did so on a 30 year mortgage. Paid a lot of interest and not a lot of principle. In 2008, sold the house and bought one for $232,800. I was able to get about $50K out of the first house and got a little smarter with a 15 year loan. Moved to a different state 9 years later. Was able to get a little more equity out of the second house. Bought my third house in 2018 for $454,000 financing close to $300K. Did that on a 10 year loan and paid it off in 21 months. I wish I was smarter with the first two houses and paid more towards the principle earlier instead of making the banks rich.

Invested $20k in a public drug company that was testing a new drug for a kind of cancer. I forget what type. It failed its trials. I lost $15k overnight

Thinking I know something about day trading...Whenever i trade frequently on emotion i lose money. I only make money when i buy it and forget about it for years.

And overpaying for a house during a bubble, lost 60k on first place. Will not buy now because of covid bubble...refuse to lose money on my house again

God. wrote:

I bet Donald Trump would grow into becoming presidential.

Lost a lot of money and lives there.

I bet I could cheat and steal millions of votes to get Joe Biden in as President.

Got caught but turned out okay as cheating is allowed.

Renovating our home tailored to what we wanted without regard to what a future buyer might want, and then having to sell it 2 years later when I got a job offer in another state. Gorgeous home with high end finishes but small square footage that didn’t justify the price. Lost about 150k on the house when you include realtor fees and everything.

Many people my age (40s) would say their biggest financial mistake was who they married. Divorce sinks you financially, period. I’m still married, but I have good friends who have absolutely been decimated by lawyers fees, alimony, and splitting of assets.

In 2015 I bought a nice house in a nice neighborhood. Previous owners had probably sunk 100K into the yard and pool. It was plenty big for my family and was in a great location.

The home value went up substantially, so I wanted to pull out the equity and get a bigger house. I made 80K off house, but made a really stupid mistake. I moved from a 500K home to a million+ new build with no yard.

I've spent over 200K on the yard and have a monthly payment twice as much as the last house.

The house is awesome, but I'd be far better off financially if I would have been happy with what I had.

Lost about 600,000 in the housing bubble. Made some bad decisions to sell rather than stick it out. It still stings to think about but we like where we landed.

I lost almost $3k on call options for AAPL and SLV while trading this summer. I only make ~$30000 a year right now so it was kind of a lot of money for me. At least I'm young and have learned my lesson about gambling with the markets.

Attending a liberal arts college for two degrees that I don’t practically apply to my career.

Lost $20 K on a grand stairway. Thought all that glitters is gold.

Whole Damned thing blew away in the whispering wind.

My running shoes have lost all their value after 2000 miles of running in them.

webby wrote:

I bought $250,000 worth of put options on Countrywide Financial that expired worthless about 3 months before the 2007 financial crisis.

Unless you had been doing similar trading for years, you actually got lucky. If you were an indice or mutual fund person and out of no where, you bought $250,000 worth of puts on Countrywide Financial. If your puts would have been in the money, you may have had to spend $250,000 in attorney fees to attempt to prove you were not trading on inside info.

Late 1990's, I had a 100% success shorting strategy trading dot.com stocks. I started going long dot.com stocks. I think S.E.C. no longer allowed dot.coms to trade on margin. I should have just been happy with my short winnings. I went long and couldn't get out quickly enough. I haven't been burnt since and I have not taken similar risk since.

going slower wrote:

My worst financial mistakes involved relationships, and my best financial decision was to not have children.

Oh come on, children are great. I’m being serious.

1. Getting married.

2. No prenup

home sweet home wrote:

Renovating our home tailored to what we wanted without regard to what a future buyer might want, and then having to sell it 2 years later when I got a job offer in another state. Gorgeous home with high end finishes but small square footage that didn’t justify the price. Lost about 150k on the house when you include realtor fees and everything.

Many people my age (40s) would say their biggest financial mistake was who they married. Divorce sinks you financially, period. I’m still married, but I have good friends who have absolutely been decimated by lawyers fees, alimony, and splitting of assets.

The lifelong negative impact on your kid’s lives is far worse than any financial impact. But the left have convinced people to only think about themselves, with bs psychobabble to ease their consciences.