I have never been much of a risk-taker. But in December 2010, I committed the career equivalent of an extreme sport: I quit a job—one that I had held for a mere two months—without anything lined up. The experience taught me a great deal about owning up to my career mistakes. After some soul-searching, I had left journalism in the fall of 2010 to join the communications team of a nonprofit. At the time, it seemed like a smart move: The pay was better, the job offered me the chance to develop some multimedia skills, and I deeply admired the organization’s mission. Within a few days of my orientation, however, it was clear that I was a poor fit for the position: The establishment was deeply bureaucratic, the role poorly defined. I was bored, and I missed journalism. I also missed wearing jeans to work, petty as that may sound. Conventional wisdom said to stick it out for at least a year, then initiate a job hunt. Yet the thought of 10 more months was overwhelming; I knew it would be bad for me professionally and personally, and bad for the organization, which deserved a fully engaged employee. So I turned in my notice to my justifiably angry supervisor, and plunged into the terrible economy without a backup plan. (I did, it’s important to note, have enough money saved to keep me fed and housed for a year; I wasn’t entirely without a parachute.) I had to humble myself and admit to my other journalism contacts that my experiment had failed. Much to my relief, however, people seemed to respect my brash decision not to stick with an unfulfilling job. They forwarded job openings and helped me find freelance gigs to fill the voids in my day and my bank account. For six months, I made a surprisingly decent living by cobbling together a half-dozen freelance jobs. Then, in the spring of 2011, I again found myself in a full-time job in journalism, with benefits. There were days—oh, so many days—when I railed against myself for having had the audacity (that millennial sense of self-indulgence, some might say) to quit my nonprofit job, giving up stability and health insurance. But the experience was an important one because it reinforced the notion that it isn’t always foolish to listen to your passions and take a risk—a calculated risk.