After years of 70-hour weeks and corporate stress, software analyst Brian Trautman bought a 53-foot sailboat, quit his Seattle consulting job, sold his house and car and most everything else, and set sail for a seven-month cruise to Australia, cutting his tether to office deadlines and work headaches. That was eight years ago, and he’s still on board.

Once a bit chubby, buttoned-up and clean-cut, Mr. Trautman now has long hair and a bushy beard. He is trim, toned and tan. But there is one thing he never imagined when he set...