re: What's the worst financial mistake you've ever made?

Too much spending on shite I didn't need right out of college. TVs. Stereos. Clothes. Etc. they say hind sight is 20/20 but instead of taking 7 years to buy a house out of college I should have could have done it in 1-2.

i can say bitcoin or a number of other lack of investing, but this is one i'm directly haunted by today.

after marriage and graduating college my wife and i bought a modest home in San Angelo for $75k in 2006. Had our first kid there. I really hated my job and started applying anywhere in Texas. Finally got a job in the fall of 08 in Belton.

The week after i got the job and gave my 2 weeks the housing market collapsed. We listed it at the same we bought it at and had 0 offers for months. then we got offers of $45k, $50k, etc. ate the cost of double mortgage (about $600) for about 6 months till we decided to rent to a family from our previous church that was having a hard time for $400 a month. it stopped the hemorrhaging for a bit.

they eventually got themselves a better situation and moved out. so we put the house back on the market, but had the same outcome of lowball offers. then our realtor asks us if we would rent and said yes. he said his MIL was moving to town and it was the perfect size for her. and he'd pay the mortgage cost exactly so we were finally net neutral on the deal. handled everything for us so we just forgot about it except for paying our mortgage every month.

then after a year, he asks if we would sell it to her and we said sure. sold it at $75k since they had done all the upkeep and made it low stress for us. made a few thousand off of it for just signing the paperwork.

then a friend from San Angelo asks if we still had the house and we said no we had just sold it. turns out that the oilfield boom of west Texas just hit and most homes had doubled or more in value in less than a month. We went and looked in our neighborhood and houses comparable to ours were selling for $150-200k and flying off the market.

if i had just been a hardass, we could have netted probably $50k.

i take a little solace in that the guy didn't screw me, and turn around and make a huge profit and his MIL still lives in the house.



TL;DR put my house on the market weeks before the housing crash in 2008. couldn't sell it and hemorrhaged money for 6 years. then sold it at my buying cost a month before our market had a rush and could have sold it for double the price i sold at if i had waited or had an ounce of self control.

Hit a trifecta at the horse track for $5100.00 my second trip to the track.

Chased that win for the next 5 years until I finally realized I'm not a good or responsible gambler.

Still remember the names of the horses:

1. Prince Lin
2. Johnny Rotten
3. Southern Sur

Giving my first wife Power of Attorney while I was deployed.

Lived in LA too long. I moved and more than doubled my income.

lost like $600 betting on the Oscars this year thanks to black panther

Career choice.

I picked something that I enjoyed rather than a well paying one. It was an absolutely horrible decision.

Got married

My wife did the same, turned out to be better for her though. Still ready to get out though since both kids are out.

Not buying more Shaw stock at $2

Not selling Calpine stock at $65