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Small business and career coach Lydia Lee has lived and worked in Mexico and Portugal, but uses Bali as her home baseHandout

The nature of work and what it means to achieve your dream job is changing. In this series, we dive into some of the most aspirational jobs coveted by a new generation.

In the early 2010s, Lydia Lee was feeling burnt out. Based in Vancouver at the time, Lee was working a full-time job as a business development director for an international education company, working long hours with no time to enjoy life or go on vacation. So, in 2012, she quit her job and started consulting, with the eventual goal of moving abroad.

Two years later, she relocated to Bali.

“I gave myself a six-month experiment of leaving Vancouver to see what it would be like to work in another time zone,” Lee says. “Could I still keep my clients? The six months turned into eight years.”

Lee is one of many digital nomads that have been growing in number since the internet made location-independent work possible in the early 2000s. Now a small-business and career coach working under the company name Screw the Cubicle, Lee has also lived and worked in Portugal and Mexico. But she keeps Bali as her new home base.

“I call myself a slow nomad because I prefer living in one place for an extended amount of time,” she says.

Seeking a better work/life balance

As the needs of workers change, most prominently with Millennials and Gen Z, the aspirational jobs of these generations are also changing. It’s not just doctors and lawyers, but a new crop of professions and work situations that are changing the definition of a “dream job.”

After quitting her Vancouver office job, Lee started her own consultancy and moved to Bali.Handout

According to a Statistics Canada study, as of February 2021, 3.1 million Canadians were working from home, with 90 per cent saying they were at least as productive as before.

And it’s not just about the lockdowns – in a global 2020 Deloitte survey of Millennial and Generation Z workers, over 60 per cent of respondents said that when the pandemic crisis is over, they would like the option to work remotely more frequently. Two-thirds of Millennials said that working remotely enables a better work/life balance. And more than half of all respondents – 56 per cent – said that if given the opportunity to work from home, they would choose to live outside of major cities where the cost of living is less.

There are a few different paths that can be taken in order to transition to life as a modern-day digital nomad. Some people, like Lee, are able to freelance or consult with a roster of clients that can be serviced from any location with a reliable internet connection.

For others, social media provides a way to work from anywhere, says Fuyuki Kurasawa, associate professor of sociology at York University in Toronto and an expert in global digital citizenship.

“Influencers gain a following by commercializing and popularizing the digital nomad lifestyle,” Kurasawa says. “One of the ways they’re making their money is through hidden or explicit sponsorships. Their travel or accommodation is paid for by a particular company for them to stay at a particular resort or place. Or there are product placements visible within a video or photo they’re shooting and posting.”

People with rare and in-demand skill sets, such as advanced computer programming, can also transition to location-independent work, Kurasawa says.

“You have some leverage as a person with a skill set that is in greater demand,” he says. “Employers know that you can find employment easily almost anywhere. So they will be more willing to bend the rules.”

Self-discipline and problem-solving skills

Given the flexibility of digital nomad careers, remote work specialist Andrea Valeria says certain soft skills are needed to succeed.

Like many digital nomads, Lee is able to consult with clients anywhere that has a reliable internet connection.Handout

“Self-discipline is important because when you get all the freedom, you get excited, and then you don’t work,” says Valeria, who is “location independent” herself and currently based in Mexico City. “You have to be resourceful and willing to solve problems that may arise because you’re not going to call your boss every two seconds.”

But when it comes to specific career paths or hard skills, Valeria says that the options are open. “Almost any job can be done remotely,” she explains. “It’s just a matter of learning the tools in order to do it remotely.”

For those eager to become digital nomads, Valeria suggests approaching your current employer. Since remote work arrangements have been in place for the past year due to the pandemic, more companies may be open to the idea since it’s been tested. Valeria recommends framing the request by explaining the impacts and benefits to your employer.

“Say things like, ‘I will be in the same time zone. I will communicate with you via X and X program,’” she says. Other examples to highlight include proficiency with digital collaboration tools and savings on office space usage.

If your employer is unwilling to allow permanent remote work, the next step may be to find a new job that is fully remote. Valeria, who runs a remote job directory, has seen an expansion in the types of positions submitted to her directory since early 2020.

“There are a lot of companies out there hiring in all different kinds of industries, from HR to accounting and legal,” she says.

To roam or not to roam?

Despite the growth in these kinds of opportunities, it is important to note that a digital nomad career isn’t an accessible lifestyle for many people, says Kurasawa.

“It requires that you are able to take risks socio-economically,” he says. “[Digital nomads] often have a cushion from family wealth, inheritance or savings that they’ve acquired.”

Your nationality and racial background can also influence whether being a digital nomad is feasible, Kurasawa adds. “You need to come from a country which has easy access to other parts of the world,” he says. “It’s also much riskier if you’re racialized because you could face forms of discrimination or even outright hostility in certain parts of the world if you’re not white.”

Kurasawa says digital nomads tend to skew younger – people in their 20s or early 30s. And we have yet to see how the first wave of digital nomads adapt as they get older, he adds.

“Once they want to have kids or a stable home, or they have health care concerns for themselves or their parents or family members, that may entice them to stay in their home base,” he says.

But the interest in digital nomad lifestyles isn’t going away for those wanting to try it for the first time.

“I think it’s going to continue amongst people in their 20s and 30s for several decades,” Kurasawa says. “The question is whether it will continue for those who hit a certain age.”

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