As more workspaces migrate to the web, getting work done at work is becoming less essential and more optional. For Greg Caplan, the idea of a mobile workspace birthed the idea for a game-changing business concept. “I was living in Chicago and working 9-5 and just felt stuck,” he explains to HOLR after a live Q&A in collaboration with Simplii Financial last month. “One day, I decided I wanted to get out and see the world. First I lined up a consulting project that I could do from anywhere.  Ultimately, I wanted to go and travel the world, but I really wanted to do it with a group of people.”


Once Greg landed a job that could be done remotely, he wanted to harness the opportunity to travel but didn’t want to do it alone. “When I couldn’t convince my friends to come with me, I put up a simple website called that asked if visitors wanted to travel the world while working remotely,” Greg reflects. It was then that Remote Year was born.


“I sent the link to a few friends and apparently they sent it to other friends,” Greg writes. “By the end of the first day, 1,000 people had signed up.” Within a few months of launching the site, Greg says that over 50,000 people signed up to participate. “That’s when Remote Year became more than just a few friends traveling the world together and morphed into a company providing this service.”

Today, Remote Year has grown into a thriving global operation, redefining the out-of-office experience for young professionals around the world. And it’s growth is not by chance.

In a survey conducted by Simplii Financial, nearly two-thirds of Canadians want to take a life sabbatical; however, taking work out of the equation isn’t always feasible. “Remote Year designs programs that make it simple for people to travel the world without quitting their jobs by enabling them to work remotely – seamlessly,” Greg explains.

Remote Year founder Greg Caplan gives a talk in collaboration with Simplii Financial at Apres Wine Bar in Toronto on January 15, 2020.

Interested? Check out the rest of our Q&A with Greg below:


HOLR: What is the criteria for the ideal Remote Year participant?

Greg Caplan: We require that everybody in our community is actively pursuing something professional.  A little over half of them are full time employees and a little less than half are independent business owners or freelancers.


HOLR: How can companies maintain a tight-knit team while members are working abroad?

GC: It definitely takes work to build and maintain relationships and culture in any environment.  People who are working in the same office or a long distance away need to actively set aside time to build get to know their co-workers and put themselves in situations where they can build trust.

HOLR: How can small businesses and young entrepreneurs benefit from the Remote Year?

GC: Living abroad is one of the most transformative things a person can do to grow both personally and professionally. It builds global perspective, adaptability, communication skills and opens your eyes to creativity and innovation. These are all skills people need to succeed in the workplace of tomorrow.


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