I quit college to travel for 2 years and played online poker as a means of income. There are parts of it I regret, like being a bit callous with money and not really knowing what I would do afterwards, but I was young (20) and having disposable income (which I regret not saving) can affect you as a kid. It should be noted that dropping out of college is NOT something I regret. I think that may have been one of the best decisions I made when I was younger.

1. By leaving school, I ended up teaching myself by traveling and experiencing different cultures, living on my own outside of my comfort zone, and meeting smart, successful people around the world. It's hard to replicate that sort of education in an institutionalized environment (not to mention how expensive a degree is).

2. I sucked at budgeting. Nowadays there are a lot of good resources online for budgeting[1] and nomading[2] that I wish I had access to back then.

3. I didn't like thinking too far into the future at the time but I didn't really have any backup plans after poker. I just assumed I would make enough to eventually invest in some other venture. I did, but that venture didn't work out too well. I eventually taught myself how to code and I've been working as a dev in SF for the past few years.

4. I would follow the nomad lifestyle[2]. Knowing which areas maximized life happiness + low cost of living would have really helped. I think anyone who has a craft that can be monetized online and doesn't have significant responsibilities (family/kids) should try work-traveling for some time.

[1] http://www.mrmoneymustache.com/

[2] https://nomadlist.com/