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Good question.. I like to say I have no regrets, because choice I've made, I wanted to do it at that moment.. and if things went bad, hopefully I at least learned a lesson. But if I had to pick...

I became a waiter after dropping out of college at 18. I seemed to have a knack for it, and I worked tons of doubles and saved lots of money until the restaurant I was at sadly closed abruptly. I had a decent sum in the bank because I had few expenses and all I did was work, so I proceeded to live off that and take the next 10 months or so off from life. In retrospect, it was a of fun and it was a great age to do it (21-22), but if I were to do it again I'd even get a part time job just to have minimal income, and work a couple days a week and siphon off my bank account more slowly. It was the most financially irresponsible decision I've made in my life.

(depending on whether or not bitcoin goes to zero =)