When I quit my first real job, I didn’t have a plan. I just walked out with the recklessness of a Harvard graduate who had come of age during the Clinton era Internet bubble. I was barely out the door when reality set in, and elation gave way to doubts about the wobbling post-Y2K economy. What if I had doomed myself to poverty? I wanted catharsis. That’s when I got the idea to jump out of an airplane.

Soon after, …