Alex Rust is 25 and working at the Chicago Board of Trade when he decides the job isn't worth the misery it's buying him. He quits, drives to Florida, and trades his minivan on Craigslist for a battered 39-foot sailboat he names Bubbles, then teaches himself to sail from a copy of "Sailing for Dummies." On New Year's Eve 2008 he leaves the dock with two friends aboard and no real plan beyond the Bahamas, and the trip stretches into a four-year circumnavigation. Director Topher Cochrane follows Rust and his rotating crew of bearded companions through storms, breakdowns, and the kind of reckless decisions that get sailors called, as one magazine put it, the worst to ever sail around the world. The film treats Rust's appetite for risk without much editorializing, letting the footage of near-misses and open ocean make the case for itself. It ends up less a sailing adventure than a study of what a person will risk to feel like his life means something.