Feelings of regret over career path?
htsh: I think its natural for an intellectually curious person to feel doubts about whatever they choose.Personally -- I studied Econ as an undergrad, worked at 2 startups for 2 years, then nonprofits for the next 3, and then law school and a big firm job.  When I was sitting in that law firm office, I hated my life relative to both the non-profit world and the startup world.  Of the 3, the startup world allowed me to live as I most liked.The thing that I miss about the startup world is that its a meritocracy.  Your knowledge and your ability will determine where you stand, not your cultural status or car or whose parents you know.  If you know more and can do more than the next guy, you have a voice that people want to hear, regardless of your age, tattoos, vices, etc.