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Kate Smith had been working nine-to-five at an advertising agency for three years when it dawned on her one day: “Is this the next 50 years of my life?”

While she enjoyed her work, the 28-year-old Canadian wanted to see the world. So, she set her sights on quitting her project manager job in the Toronto area to travel, while she planned her next steps. It was then that she came across Remote Year, which puts together groups of 75 professionals to hop across three continents for an entire year, one city at a time, all while working remotely as digital nomads.

The programme of long-term travel comes without the need to take time away from work or lose out on pay. For Smith, the idea of travelling with a group of likeminded professionals who were also keen to learn about new cultures and ideas was appealing—particularly since someone else would take care of the logistics.

It’s a hefty price to pay

Of course, having someone else handle the details of a nomadic work life comes at a pretty steep price. Smith was one of 25,000 people who applied to be a part of Remote Year’s inaugural in 2015. When she was accepted, she flew to Prague (the first of 12 pre-arranged destinations) and found a remote job as a digital marketing consultant. She says the pay was on par with her previous work, but Remote Year’s fee was a hefty $27,000.

Kate Smith spent 2015 travelling the world as part of a $27,000 digital nomad programme (Credit: Kate Smith)

“It’s a hefty price to pay,” she acknowledges. “But what made the programme worth it for me – and what I miss the most now that I’m on my own – was the community.”

A 2014 study from MBO Partners, a consultancy, found that 22% of all independent workers they surveyed reported less than 10% of their revenue came from their local area. And with a growing number of people who can work remotely — either for one employer or in a freelance role—this is expected to grow. And last year, Bridge Street, a research firm, found that while most workers were tied to a location, 75% would prefer to live as digital nomads.

But the idea of curated digital nomad experiences has proven popular and spawned a handful of similar programs such as Wifi Tribe, WeRoam and CoWorkTheWorld, all of which have stringent vetting processes (including lengthy applications and numerous interviews) to foster a sense of exclusivity and help would-be digital nomads break free from the traditional office space.

The $27,000 fee took a financial toll and limited her ability to see as much as she wanted in each location

The fee Smith paid included $5,000 upfront and $2,000 per month for the first 11 months to cover monthly professional development events, private accommodation, shared workspaces with Internet access and travel between all 12 destinations (participants move to a new city each month, largely due to 30-day restrictions on tourist visas). Smith says she earned enough to cover her costs, but the $27,000 fee took a financial toll and limited her ability to see as much as she wanted in each location.

Those on formal digital nomad programmes enjoy the camaraderie that comes with group travel (Credit: Remote Year)

A new breed

Dutchman Pieter Levels is the founder of Nomad List, a social network for digital nomads that connects travellers through chats, forums and meet-ups around the world. He says the various “tribes” that nomads can join are frequent topics of discussion on the forums.

“I think the people paying $2,000 a month for group travel are very different than the digital nomads we’ve seen up until now who enjoy the solitude, random adventure and serendipity of travel,” he explains. “Many of them are corporate workers who use it as somewhat of a sabbatical year.”

This isn’t what you traditionally think of as your digital nomad

Levels says organising travel, workspaces and accommodation yourself, all while being alone for long stretches of time, can be a daunting endeavour. These programmes remove traditional barriers, including the intricate travel planning and social isolation.

“This isn’t what you traditionally think of as your digital nomad with a freelance or flexible-by-design lifestyle,” explains explains Greg Caplan, founder of Remote Year. “These are people who have figured out a way to make it work within their current vocation.”

People on the Remote Year programme travel to 12 destinations around the world to work – for a fee (Credit: Remote Year)

Participants in Remote Year come from 40 different countries and most are in the 25 to 35 age group, though it ranges from 22 to 65 years old. And while the archetypal digital nomad may work in technology, Caplan says the majority of professionals on Remote Year have marketing jobs. There are also consultants, accountants, journalists, lawyers and salespeople.

Remote Year and WeRoam both have corporate partnership programmes aimed at HR departments who may be looking for non-monetary benefits to offer employees.

Study abroad for adults

Jennifer Deal, senior research scientist at the Center for Creative Leadership in San Diego and author of the book What Millennials Want from Work, likens programmes like Remote Year and WeRoam to a post-collegiate version of studying abroad.

You learn so much about yourself, but you’re not going to go back and do all over

“Years ago if you wanted to study overseas you had to arrange it all yourself, but now, most universities have built this option into the school,” she explains. These remote working programmes serve a similar purpose for professionals, and “are like taking a year abroad except you’ve finished school and are getting a paycheque.”

Deal also thinks it makes perfect sense that organised work-travel schemes would appeal to Millennials, particularly ones who don’t yet have a family and work in professions conducive to remote work. “It fits their desire to do the work they want to do where they want to do it,” she says.

For Smith, the biggest thing travelling with Remote Year did was expose her to a way of living she didn’t understand before. She says she’ll never work in an office again.

But that doesn’t mean Smith would sign up for a second time, likening it to going to university.  “It’s the best years of your life and you learn so much about yourself, but you’re not going to go back and do all over,” she says.

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