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The Digital Nomad Life

  • Brenda Bouw
  • |
  • Mar 23, 2020

Alumni are earning a living while travelling the world – all on their own terms.

The Digital Nomad Life

It was while working for McKinsey & Company that Jared Schachter, HBA ’13, got a taste for what it’s like to work in far-flung destinations like Australia and Mexico.

“I’ve always loved travelling,” says Schachter, who also went on exchange to Milan during his time at Ivey and has travelled to 20 European countries.

In 2015, Schachter joined Uber Technologies Inc. in Toronto and then moved to the company’s San Francisco office before going out on his own as a freelance management consultant with a goal of being able to live in different locations throughout the year.

“I love being able to do everything on my own terms... and I don’t crave vacations like I used to,” says Schachter, who was pushed to go independent by his girlfriend, Sam, who is also a freelance consultant.

The couple not only wanted to be their own bosses, but have the option to mix work with travel whenever they choose. Today, they split their time between San Francisco, Schachter’s hometown of Vancouver, Sam’s place in Toronto, and other parts of the world. They spent the first four months of 2019 in South America and, this year, their plans include stints in places such as Costa Rica, Europe, and Colombia.

Schachter is among a growing number of digital nomads — workers who earn a living while travelling the world. Unlike telecommuters, or employees who are assigned to work in foreign countries, digital nomads work from anywhere in the world they choose, and they often switch it up after a few months.

“A digital nomad is the extreme extension of telecommuting,” says Rahaf Harfoush, HBA ’06, a digital anthropologist and author. “They build their work/life routines around wanting to move and live in different places to experience different cultures.”

Harfoush says the trend is powered by technology, and that the Internet enables people to work from anywhere. It’s also driven by millennials and Generation Z who are seeking a different working lifestyle than generations before them.

“They’re pursuing a type of work/life balance that’s quite new,” and goes beyond just having a two-week vacation, says Harfoush. “It’s this idea of building a life that’s anchored in experiences and discovering the world, immersing yourself in culture, and going after the type of knowledge that you would only really get after being in a place for a couple of months.”

The high cost of living in major cities such as New York, San Francisco, Toronto, and Vancouver is also inspiring young people to move around instead of settling down, she says.

“It’s like a life hack where they realize that through these technological platforms they can access first-class labour markets in cities with a much lower cost of living,” Harfoush says. “It’s evolved partly out of necessity, with people frustrated by the lack of options.”

Illustration of a man walking and carrying a laptop

The digital nomad lifestyle isn’t for everyone, Harfoush says. And it’s not a lifestyle most people pursue long term. “At some point, there comes a time when you want roots and more long-term stability.”

“The good news is there’s never been a better opportunity to create a nomadic lifestyle that works for you,” she says. “There are an infinite number of ways to tackle it.”

Digital nomads are mostly freelance workers and bosses, but there are more companies also offering the alternative working arrangement for employees.

Last year, Schachter started working as Head of Product at, a company with a remote team that’s creating products for digital nomads like him, starting with travel medical insurance.

Schachter says his geographic location remains his choice, but he anticipates a time will come when he settles down in one city. He recommends people interested in the digital nomad lifestyle do it earlier in life, when they tend to have fewer commitments.

“It’s a very cool life experience if you enjoy travelling and doing new things… while you are able and have the energy to do it,” says Schachter. “I know I won’t be able to do it later in life.”

The downside of the nomad life is the lack of routine and regular access to your friends and community, says Schachter. For instance, it’s often up to him to connect with friends when he’s back in Vancouver. “Nobody knows when you’re around so you have to put more effort into maintaining relationships.”

Andrew Parkes, HBA ’03, is also pursuing the digital nomad lifestyle through Leverage, a company that helps small business owners and entrepreneurs to outsource and scale their companies. All of its 50 employees, including Parkes, Director of Growth, are remote workers.

Parkes started working at Leverage as a side gig, while commuting an hour each way from his home in Burlington, Ont. to an account executive job in Mississauga, Ont. He took the leap to work full time for Leverage in August 2018 and moved to the small town of Stratford, Ont.

“Working for Leverage in a fully remote capacity has allowed my family to move away from the Greater Toronto Area to Stratford where real estate is cheaper and issues like traffic and congestion are non-existent,” says Parkes, whose wife now also works remotely doing online training for dental hygienists.

The couple, who has two kids, spent the month of February in Mexico, and plans to increase that to three months in 2021. They’re looking into ways to continue their children’s schooling while away.

“The biggest benefit is the freedom and flexibility,” Parkes says. “As long as I have an Internet connection, I can work.”

While there’s no official closing time, he says the lifestyle forces him to be self-disciplined when it comes to both opening and closing his computer to maintain work-life balance.

Parkes also brushes off any suggestion that people don’t work as hard when they’re doing it from an exotic locale. “You can still be very effective,” he says. “It’s not about how much time you’re logging. It’s about how efficient you’re working.”

“I am a huge proponent of digital nomadism as it provides the freedom to live and work from wherever. I am free from a physical office and I plan to never go back!”

Illustrations: Wenting Li
Art Direction: Greg Salmela, Aegis