“Many clients don’t know how big to dream,” Wealthfront’s Carroll said.

When the Parrishes were envisioning their trip, the Wealthfront tool didn’t exist yet, but they spent three years planning and saving. It helped that they already had a good start on retirement saving. In his early 20s, Kyle began putting as much as possible in his 401(k) plan, accumulating more than $150,000 by the time they left. While they traveled, they carefully tracked every expense in a spreadsheet so they didn’t overspend.

And After?

There’s one risk that Wealthfront can’t help clients with: the possibility that a yearslong break could derail their careers.

As stay-at-home parents know well, a key worry for anyone leaving the job market is how to get back in. The U.S. unemployment rate is at near-record lows, but there’s no guarantee that will last. You could leave a well-paying gig in a hot field and return to find the economy in recession and jobs scarce.

It helps to work in an industry where employers aren’t turned off by gaps in your résumé.

In advertising, “it’s to my benefit to be an interesting person,” said Andrew Wind, 38. He started planning a trip around the world almost five years ago, before he took a job as a creative director at a salary that allowed him to save the $40,000 he figures he’ll need.

Three months into his trip with a year to go, his plans are ambitious: visit about 30 countries and 45 cities, finish writing a book, some screenplays and TV pilots, while also learning to be conversational in French and Spanish. “I’m actually more productive when I travel than when I’m home,” he joked, on the phone from Munich, Germany.

He also expects to be a better employee after the trip—assuming he ends up deciding to go back to advertising, or the U.S., at all. By then, he said, “I’m really going to want to buckle down and start the next chapter of my career.” 

Similarly, when the Parrishes returned to San Francisco, their trip was less an obstacle to their job hunt than an asset, a way to break the ice while networking. Within six weeks, both found new jobs that paid more than their previous ones.