This summer, my friend Rachel Bailey was working as a waitress in Athens, Ga., doing social media for some restaurants, writing when she could, but not as much as she wanted—just scraping by in a town where it’s easy, sometimes even fun, to just scrape by. But she wasn’t having fun. She’d been out of college a few years and had imagined something more for her 20s. She was feeling anxious, stagnant and just generally crappy about life. And then she hit her head in a piggybacking accident and almost died. And then things got better.
Risk scares me because I view the squirmy unknown as a thing to be tamed, to be tamped down and placed neatly in a box. If I do the same things every single day, in the same way, the outcome is most likely something that I can predict.
The summer of 2005 was a fine time to be 26 and an even finer time to have a dream. All around me, people were going big by purchasing homes or committing as heavily as they could to can’t-miss ventures or, in a lot of cases, reinventing themselves entirely: friends and colleagues were moving into two-, three- and four-bedroom "smart investments" all across Chicagoland while locked in an arms race with people "chasing the dream" in oddball lines of work to see who could "live more fully." I, wise young man that I was, set my heart on joining the ranks of the latter.