I dropped out of grad school (MIT EECS) when I got up one day and realized I was only in it because it had seemed like a good career path, not something I was fired up about. I was doing reasonably well but not killing it by any stretch, but definitely could have wrapped it up and put that on my resume. Instead I just... didn't. I did f--- all for a few weeks (aside from a copious amount of bar hopping). Had a really awkward call with my parents. Then I pounded the pavement for work and used it as my calling card.

Company (all fairly small / start up level): Tell us about yourself.

Me: Got into MIT for grad school. Decided I wanted to get going doing things, not learning theory. Took a chance on myself and walked out the door with more debt than I'd like to think about but excited to see where my talent and ambition would take me.

Had three offers in the first ~10 days, took one, loved it for about six months, moved on. Almost three years later I've landed in a great spot, make a nice living, don't regret it for an instant.