Taking a Remote Year is Now a Fast-Growing Trend

It all started with an online request for travel buddies.

At 26-years-old, the daily grind was already taking its toll on Greg Caplan in 2014. “I was living in Chicago, working a 9-to-5, commuting every day in a sea of people, and feeling a complete lack of inspiration. I felt stuck. I wanted to get out of Chicago — I grew up there — and I wanted to travel,” said Caplan at a Toronto event hosted by Simplii Financial. “The first thing I did was line up some remote work with a consulting contract that I could do from anywhere. The next step was to go travelling, but I wanted other people; I didn’t want to go alone.” 

Caplan’s friends — all of whom enjoyed traditional corporate careers — didn’t exactly share his enthusiasm for getting remote jobs and travelling when he pitched the idea at dinner one night. “So, the next day, I put up a website and it said, ‘Who wants to travel for a year while working remotely?’ I sent the link to friends; they sent it to friends, and it kept getting shared. The first day, over 1000 people signed up and journalists across North America and overseas began picking up the story,” said Caplan. “In a few months, over 50,000 people signed up. That’s when this went from my desperate plea for people to travel with to a business idea, and soon after, Remote Year was launched.”

Remote Year supports the digital nomad cause by helping you live your best life personally and professionally in some of the most vibrant, culture-rich, and scenic places in the world — from across Europe, to Southeast Asia and South Africa, and more. The programs range from one month to one year, with the yearlong program placing you in a different (Wi-Fi-abundant) spot each month. At the core of the Remote Year community is a 24/7 co-working space, where a community of professionals can clock in hours before embarking on things like African safaris, hot air balloon rides over Mexico’s pyramids, or wine tasting excursions at some of the world’s best vineyards. Each fully equipped apartment is within a 10 to 15 minute walk from the co-working space.

It’s safe to say there’s definitely a market for the cause. There’s no denying that being a digital nomad has its appeal, as a growing number of people seem to share the sentiment. Most of today’s professionals simply won’t accept the monotony of the 9-to-5 grind for a prolonged period of time — and they don’t have to. It seems today’s urban professionals increasingly crave experiences over things (something that’s inevitably fuelled by social media for the younger generation), possess a thirst for new cultures, and seek mobility on the career front; a desire to take their jobs outside of the often uninspiring office.

Remote Year promises to facilitate the transition into the remote workplace by working with existing employers (i.e. convincing them that remote work makes sense). Upon arrival, applicants — who have ranged in age from 22 to 78, with a sweet spot of early 30-somethings — typically have a job that allows them to work remotely or have freelance work lined up. 

But, what’s the cost?

For a price tag of about $2000 to $2300 per month, Remote Year takes care of booking your workspace, accommodations, local experiences, events, and more. “It compares very nicely to rent in many Canadian cities,” says Caplan. “If you’re paying for rent and a co-working space in Toronto or Vancouver, it’s a pretty similar figure. But you get everything else included; all the travel between destinations, private apartment-style accommodation, a private co-working space, and events and activities.” 

While this cost is indeed comparable, you can obviously expect Remote Year to dent the wallet if you’re still paying for your pad back home. In cities like Vancouver and Toronto, giving up a decent rental unit in this market – especially if you’ve lived there for years and subsequently experienced minimal increases in rent – is a complicated idea to grapple with. Most downtown condo buildings don’t allow short-term rentals, especially if you’re a renter yourself,  so you should expect to pay rent on your place, or give it up. Furthermore, the monthly cost doesn’t include a deposit, or your initial departure flight and flight home. 

To many, the whole rental decision and cost, however, is a worthwhile sacrifice for what Caplan describes as “life-changing” experiences. “I personally spent most of my time in Mexico City. It’s a great place and 23 degrees year-round. It has great food, unbelievable urban architecture, and the best part is that it’s covered in green space. So it’s warm, vast, and beautiful and it’s a place I’d recommend to anyone,” said Caplan when asked about his top spots. “Here, we’ll do everything from street taco excursions, to lucha libre matches.”

Caplan also spent a month in Cape Town, South Africa last year,  another popular Remote Year destination. “I love it there; you have to check out wine country. I love to head down the Cape, where you’re literally covered in nature, surrounded by ocean,” said Caplan. “Another incredible experience involves swimming in the water next to penguins at Boulders Beach. And, of course, a safari is a must.  Seeing the ‘big five’ in their natural habitat is one of the most life-changing things you can do. It’s an unbelievable and inspiring place to be.” 

Of course, you can also do all of this independently and – as a search of online reviews reveals – the Remote Year experience is not for everyone, even if your wallet is thick enough. But, in the dark depths of a Canadian winter — an especially isolating time for the work-from-home set — the prospect can’t help but sound
quite appealing.