Dialing In From Paradise

Caroline McCarthy


“I’ve been campaigning for Iceland for years,” entrepreneur Amit Gupta tells me. But he’s not referring to politics; rather, he’s musing about the next destination where he’ll take the entire workforce of his company, Photojojo, a beloved retail site for digital photography enthusiasts.

Since 2010, one of Photojojo’s company policies has been that each year the entire workforce of the startup (which in 2014 was about 12 people) packs up and heads to an exotic location for several weeks of relaxation, exploration, and creative thought – yes, in the sense that’s relevant to work – on the company dime. The first time, they headed to the Indian resort city of Goa. Then it was Puerto Vallarta, Mexico; then Phuket, Thailand; and most recently, it was Guanacaste, Costa Rica. As for Gupta’s dreams of Iceland? They may never materialize, because he admits his employees seem to prefer beaches to high-latitude volcanic hot springs.

SCENE FROM ONE OF PHOTOJOJO’S RECENT WORKCATIONS. PHOTO CURTESY OF AMIT GUPTA.

Meet the “workcation.” It’s longer than a traditional offsite, more work-focused than a retreat, and often more balance- and wellness-focused than any corporate function would have been up until the past decade or so.

To the outsider, the idea of a cadre of tech startup employees peering at their MacBook Air screens from the comfort of hammocks string between palm trees, or discussing new user interfaces with mojitos in-hand under a canopy of tropical constellations, may seem like excess worthy of HBO’s satire “Silicon Valley.” Yet devotees of the “workcation” insist it’s not financially profligate, but rather a smart solution for the 21st-century startup climate, where increasingly companies have remote employees in far-flung locations who rarely are able to work face-to-face. “It’s valuable for the creative ideas that we always seem to come up with and can’t wait to implement when we get back,” Gupta says. “The day-to-day grind can make it hard to set time aside to explore new ideas, especially with everyone at once. Something about bringing everyone together to one house, making sure random and chance encounters and conversations happen continually, and removing the distraction of day-to-day life and obligations back home gets people thinking in ways they wouldn’t otherwise.”

Indeed, the number of remote workers in the U.S. has risen a whopping 79 percent since 2005 and continues to climb. Which is why founders like Courtney Boyd Myers, head of consultancy Audience.io, which helps U.S.-based companies internationalize to Europe and vice versa, have jumped on the “workcation” bandwagon She, too, runs a company whose employees (currently, 4 of them) are spread remotely across time zones and benefit from face time wherever it may be. “When we get to spend huge chunks of time together, we really get to bond as human beings, deepening and strengthening our team relationships,” Boyd Myers says. “We also schedule in a lot of ‘big vision’ and ‘state of the company’ discussions, which help us to all get on the same page and share our ideas for the future.”

What does a typical day look like? For Gupta’s team at Photojojo, it starts with a team breakfast, followed by structured brainstorming sessions, a team lunch, and then an afternoon that may be dedicated to more “collaborative ideation,” as he puts it, or perhaps time at the beach. Every few days there’s a “free day” for a field trip. “We’re spending a ton of time hanging out with each other, exploring, working, talking,” he says. “I definitely get to know some of the people I work with better in these two weeks than I do in a year of working with them.”

ANOTHER MOMENT FROM ONE OF PHOTOJOJO’S WORKCATIONS CAPTURED BY AMIT GUPTA.

It’s similar for the Audience.io team, Courtney Boyd Myers explains. In addition to group brainstorming and collaboration when they rent an Airbnb vacation house together and take a “workcation,” there’s plenty of time for yoga classes and visits to local tech startup hubs and workspaces.

The tricky question for any small company dedicated to team getaways is the question of growth. If “workcations” are so good for company productivity, presumably that’ll mean the company grows more successful and hires more, right? And then, the team might grow too large to pack everything up and fly to Nicaragua or Morocco for a few weeks?

Both Amit Gupta and Courtney Boyd Myers hold out hope. Gupta points out that in this year’s retreat to Guanacaste, several Photojojo employees who have families with small children were still able to make the “workcation” fit their schedules. “I do think it gets harder to find locations that can accommodate teams of double our size, but with planning it’s definitely doable,” he says.

“Maybe we won’t be able to cover 30 people’s airfares and dinners out every night,” Boyd Myers says. “But I hope we’ll always be able to at least cover the Airbnb!”


Currently the Vice President at Communications and Content at true[X] media, Caroline McCarthy has been a journalist since the age of 21, covering a smattering of digital media, social networking, marketing, entrepreneurship, and innovation.

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