It's not as if Jared Heyman had never before thought of escaping his life. Ever since a summer romance in Costa Rica on a trip after high school, Heyman had fantasized about life on the road, spinning dreams of his own Che Guevara-like Motorcycle Diaries. The problem was that in the real world, Heyman had more than succeeded as a driven businessman—an entrepreneur with a myriad of fires to put out and responsibilities to live up to at Infosurv, the Atlanta-based market research company he had founded in 1998. It was exciting in its way, but Heyman was aching for a change. In 2010, at 32, Jared finally decided he wanted a break—a really big break.

After months of planning his escape and prepping his staff, Heyman left his entire world behind in July. The plan: travel for a year, spend a lot of time on a lot of beaches, pick up a language or two, and learn to kite surf. The only vestige of his former life he brought along when he boarded a plane bound for the West Coast and beyond was his girlfriend of two and a half years, Lauren Goldstein. But she would fade out of the picture in a matter of months. "Being free and unencumbered is probably the biggest thing that motivates me," Heyman would later tell me.

Rather than push ahead with Infosurv, which he launched at the tender age of 20 and had built into a $2.1 million company, he was leaving it behind in the hands of a few trusted employees. So what if he had just developed a product he hoped would propel his company to the next level? Heyman decided there would never be a better time—there would always be a reason not to go—and that his staff could manage the business without him. In fact, he promised to bow out of running Infosurv completely during his sabbatical, with the exception of reading a weekly e-mail update and checking in with a phone call every now and then.

When I caught up with Heyman and Goldstein on the beach in Santa Monica, California, they had been traveling for a couple of weeks a...