LIFE WAS GOOD for Krista Jancik. At 35, she was working as an art director at an advertising agency and living in the trendy West Loop neighborhood of Chicago. Still, she said, “Everything was feeling a little too routine.” Initially, Ms. Jancik considered planning a big vacation—China, maybe, or Australia—but then she came across an ad for Remote Year: a fledgling travel company that spirits groups of remote workers away on a year-long journey around the world. Though Ms. Jancik’s job was not conceived as a remote position, within weeks, she’d sold her company on the benefits of such an experience, broken her lease...