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.

About 80% of my Steam library.

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.

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.

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).

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.

Waiting for the bubble to burst before buying a house.

Anytime now…

When I was young I bought a brand new motor cycle from a dealership. Did I mention that I didn’t know how to ride a motorcycle when I bought it?

Changed over the ownership of the house I bought with my own money to my now ex because he was the one with the job. Am now house-less and renting an apartment at triple the mortgage payments.

University

I spent 50 grand and 4 years of my life to be told by prospective employers that I either lacked real world experience, or that I was overqualified. It took me another 3 years to find a job after university - one that doesn’t require training and is barely relevant to my field.

I get to hang a pretty piece of paper up on my wall, I guess.

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…

Not a big one, but surely the worst one. There was a “make your own perfume” stall in our college fest. I didn’t like the fragrance of most of what they had to offer. It took me time to pick one, but I picked one that I thought was the most unique one.

Then when I came home, I realised it smelt exactly like my dad’s car freshner.

My first wife.

I was conned into going into ITT Tech out of high school. I learned a lot but didn’t find out until later it was unaccredited so nothing would transfer to colleges and that they had lied heavily about their placement numbers. There were a few issues keeping from going after them: it was my parent’s money, the point in time I went wasn’t part of the lawsuit, and my parents were dead when the lawsuit came about. I cannot put ITT Tech on my resume because of everything related to it, it’s a literal black mark. So I have to stretch the truth of those two years because of it.

I used to sell plasma, and I used the funds on Robinhood to try investing without affecting my regular cash flow. Through sheer luck, in one day, my account went from around $200 to over $2500. I was overjoyed. I’d clearly made a genius-level decision that would only continue to pay out.

Anyway, I woke up the next day with less than I’d had to start. Should’ve taken the money and run. Or not tried to time the market. Either way, it felt like I’d lost $2300 instead of $50.