Early in my software dev career I had a contract job at a young company called Microsoft. Without going into boring details, what I saw in terms of miscommunication, wasteful practices, and odd behaviors by overstressed managers led me to see it as a typical startup that was outgrowing its ability to run itself. At that time they were handing out full-time employment like candy - most of the programmers in my hallway got converted - but I left, because I didn’t think the company would go anywhere. This was two or three years before the stock went nuts and programmers there became millionaires in their twenties.

Not applying for scholarships. I didn’t have my mental health under control in high school and just didn’t apply for any. Not even the one I was guaranteed…

Worst would’ve been having a kid at 21, second worse was. It grasping how predatory credit cards can be. Survived the first but the 2nd one hurt the longest, now I treat credit cards like poison, I try to avoid carrying a balance at all costs and expend any extra funds to eliminate any balances before I look at other possible uses of that cash.

Rolling over a payday loan. You write them a check for $300 post dated for payday, they hand you $255. On payday, I would go back with a fresh $300 check to replace the one they just cashed so they could hand me another $255. This would be after exhausting overdraft from my checking that cost something like $35 to overdraw by $200. I wasn’t even on hard drugs or drinking, just weed and nicotine. By the time I was 30 I had $15k in financial judgements against me, it took another 4 years to pay everything off. It almost cost me a promotion during the credit check. Apparently you shouldn’t be a financial advisor if you’re terrible with your own finances but I talked my way out of it (and then failed as a financial advisor).

Not the worst, but the weirdest:

When I got my first credit card they told me that the very first transaction would be divided into 12 monthly payments, with no interest. So my first purchase was a new cellphone that I needed.

Later the same day I bought something for like a dollar, and just to be funny I paid it with the credit card.

Well, that $1 dollar purchase was also divided into 12 payments. Nothing bad happened because of that, but it just felt stupid.

Faceplanted off a Lime scooter. $6700 to remove and replace a tooth.

When I was 25 I was making a lot of money. So I bought my childhood dream car, you know the one you have on your wall with the chick in a bikini on the hood. So I bought a '98 Diablo VT with I believe around 3k miles (this was in 2001). It was the absolute piece of shit. Don’t get me wrong, it was gorgeous and sounded twice as sexy. But I shit you not, every other time it left the garage the most random shit would break, crap that shouldn’t break on a car with 3k miles and 3 years old. Spark plugs were fowled, radiator hose blew, wires would be frayed and cause electrical issues. It was like non-stop. I soldnit for a 20k loss.

Mind you I’m 43 now and own 9 cars, 4 motorcycles, and grew up building engines with my dad. So I have no issues working on cars or doing whatever. I can tell tell you outside of Jeep, that Lamborghini was the biggest piece of mentally handicapped engineered vehicle I’ve ever seen.

Quit my job start of this year. Thought I could start a self employed thing with a secure client but they bailed (turns out they just went with my previous employer for lower prices).

My first wife.

so I bought a cheap old Porsche…I realize now there is no such thing.

I bought a fully restored Jeep Grand Cherokee with steel bumpers. It gets 9 mpg. It’s pretty bad ass. Now it costs me $100 to go to Sequoia NP from Fresno. So now it’s just sitting. I got a super good deal on it. Dude I bought it from spent 40k to restore it. I got it for $10k. Gas bill is killing me so it’s just sitting.

Dyson vacuum robot.

not stop my mom from doing the worst finnacial decisions possible

Should have bought Gazillion sticks of ram

Waiting for the bubble to burst before buying a house.

Anytime now…