Moonshots: I dropped out of school with only a year left to graduate because the Web development startup I launched with two of my friends was getting out of control. We were charging over $100/hr in the 90s and still having to turn down clients. We worked on amazing projects I can barely remember and made a pile of cash. But we were kids and couldn't get along so we split. I joined another startup that got bought out and put more cash in my pocket which led to me following leadership to yet another startup... that died pretty hard in the Fall of 2001.
Aftermath: Money, parties, travel, and then boom... it was over. Although I had been an irresponsible child with my earnings, I had the good fortune of having some saved some before I was laid off - and I could collect unemployment benefits.
Like everyone else, I couldn't find work anywhere. There was a flash cartoon back then called "Laid off: a day in the life". Good times, good times. I went back to school to finish earning my BS in CS. While in school I tried desperately to get a job in the service industry. I couldn't even land a job waiting tables. Managers told me that they had plenty of people that could work at any time and they didn't want to fuss with people who had school schedules. One manager told me he had over 1,500 applicants at his new restaurant. After having held a Director title in 2001, I ended up starting over again with a fresh degree and a job as a Jr Videogame Programmer in 2003. At least I was working on videogames instead of web! (spoiler, I'm back in web, but that's another story)
I still don't think I've fully come to terms with the unrealistic expectations I developed early in my career. I rose to success quickly because I had a head start in web tech just as the industry around it was taking off. After the crash I had to work hard for things like everyone else which means coming to terms with the realization that I am not as special as I thought I was.