I've known a few people in this situation. If you're feeling completely burned out, you might want to chill out and travel around for a few weeks (or whatever)

I've known a few people in this situation. If you're feeling completely burned out, you might want to chill out and travel around for a few weeks (or whatever) to clear your head. After that: - If you want, go back and get your degree (it only gets harder as you get older) - Do an entrepreneur-in-residence gig (instead of an associate.) From what I've seen, EIRs do anything from hanging out and shooting the shit all day (i.e. very little) to reviewing investments/networking/helping portfolio companies to actively incubating their next idea (or a bunch of ideas simultaneously) - Join a growing startup that is past the ramen-fueled-fight-for-survival frenzy, which might be a good balance of upside vs expected value. A lot of former YC founders do this if their companies don't work out. As a current venture-backed founder/CEO, I can say with certainty that your startup experience would be highly valued. - Join Google, Microsoft, or Facebook, check your dreams at the door, and ride out comfortably into a middle-aged sunset (I kid, I kid.) Feel free to email me at drew at dropbox[dot]com if you want stories or intros to people who have been through this.