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An Inside Look at Digital Nomadism: From Worker to Employer

Can you work remotely while traveling the world?

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Table of Contents

  1. 1. What is a Digital Nomad?
  2. 2. The Social Challenges of Digital Nomadism
  3. 3. Sharing the Journey
  4. 4. The Rise in Flexible Workplace Cultures
I have the freedom to be where I want – for as long as I want – without having to ask anyone for permission.
- Rachel Story, digital nomad, online English teacher,
and co-owner of

The main benefit of working remotely is undoubtedly the freedom associated with not being tied to the traditional 9 to 5 office job. However, remote employment offers opportunities beyond working from the comfort of home (in your pajamas), or while sipping artisan drip coffee from a makeshift work station in the corner of your neighborhood coffee haunt.

According to a report published in 2019 by The Guardian, a recent study conducted by the research firm MBO Partners revealed that 4.8 million US citizens identify as digital nomads. Additionally, an earlier Gallup poll revealed that 43% of employed Americans execute at least partial work from outside the office. And, with more and more remote working opportunities available due to the pandemic, once it is safe to travel again, the concept of digital nomadism may gain even more traction within the American remote working culture.

What is a Digital Nomad?

A digital nomad is a person who is employed through the use of telecommunication technologies, which allows the worker to live a nomadic way of life. Furthermore, digital nomads may work full-time hours from outside the office, or as independent contractors, allowing the freedom to work with as many clients as desired. Digital nomads travel from place to place and work remotely from coworking spaces, coffee shops, libraries, or anywhere they can access power sources and WiFi to get their work done.

According to digital nomad Rachel Story, it’s the freedom her lifestyle awards her and her husband Sasha, who have been at it for 4 years now, that is valued most. “I have the freedom to be where I want – for as long as I want – without having to ask anyone for permission," says the online English teacher and co-owner of the blog Grateful Gypsies. “The lack of a home, a car, and other material possessions give me the independence to travel indefinitely if I so choose.”

Story and her husband, who are originally from Tennessee and Michigan, respectively, have traveled from China to Bali in Asia, to Brazil and Peru in South America in recent years, along with stints from Mexico to Guatemala. For work, the duo splits time between teaching English online for three different companies, along with spearheading content for Grateful Gypsies and other travel blogs. “For me, personally, finding a work/travel balance has been a little tricky,” explains Story. “One of the biggest changes we’ve had to make is our travel speed.”

As a digital nomad, Story shares, your time can be divided into three categories: work time, sightseeing time, and time spent socializing. She adds, “The latter is whatever you enjoy doing for entertainment. For us, it’s seeing live music and checking out the nightlife.” 

However, Story says it’s nearly impossible to fit all three aspects into one day. Sometimes, achieving even 2 of these categories can be tough, so the couple tries to spend more time in fewer places in an attempt to “do it all.”

The Social Challenges of Digital Nomadism

This lifestyle, on the other hand, does have its drawbacks. “Traveling as a digital nomad can get pretty lonely,” says Story, who once spent a gap year backpacking with her husband staying in hostels, which offered social atmospheres and easy ways to meet people. “But, our work as online English teachers won’t help us make friends in hostels,” she continues. 

As a result, Story now opts for lodging through Airbnb and rental homes. “We’ve had to become very intentional about meeting people in the places we’re visiting. There are usually lots of ways to do this – going to events at hostels, joining local Facebook communities, and co-working spaces have been our favorites.”

Sharing the Journey

More recently, Story has shifted gears toward developing more digital nomad content for Grateful Gypsies, which offers a resource to both aspiring and established digital nomads. “We have tons of helpful content about how to become a digital nomad, and then help you plan your travels once you’ve made the transition,” she says. “I truly believe the fastest way to achieve this lifestyle is to start teaching English online, and I even wrote a free e-book about it.”

In addition, for those on the fence about trying out the digital nomad lifestyle, Story offers some words of wisdom. “You should definitely do some preparation and planning, but you can’t plan for everything, so, the easiest way to learn is to go do it!”

The Rise in Flexible Workplace Cultures

Publisher of East End Taste Magazine based in the Hamptons, Vanessa Gordon is at the helm of this niche food, drink, and travel outlet, with both digital and social media platforms. And, of her 11-person team of developers, editors, writers, and virtual assistants, all but one worker are based remotely, with 2 being digital nomads. 

“I actually was very drawn to their working lifestyle and way of life,” says Gordon. “It meshes so well with the East End Taste brand. They are always meeting new individuals and are gaining so many vast, new experiences. It really is who they meet and connect with that has been the most helpful.” 

Through her pair of nomads, Gordon says she has created relationships with photographers, writers, and even manufacturers for e-commerce around the world. For example, because of one particular connection, she is now in the process of creating an e-commerce business for East End Taste for the first time.

According to Gordon, her flexible workplace ethics developed on their own. She knew that running an indie publication could not afford her the staffing luxuries of mainstream media outlets, but the remote work relationship seems to be favorable for her brand. “I encourage flexibility in the workplace. I want those who work for me to feel at peace and happy with their surroundings,” she says.

Moreover, Gordon says that her digital nomads are anything but disruptive to her business. “I believe it is a very positive aspect,” she admits. “I honestly wish everyone who worked for me was able to travel more often and create new experiences from their different and unique work environments. It changes you for the better – and molds you into an even greater, better-rounded individual.”

As for the impact of the pandemic on the remote working community, Gordon is an advocate for the rise of the digital nomad to even greater heights, once travel becomes safe again. “The more places we go and the more people we meet along the way, the more we learn,” she offers. “I believe there will be a huge boom in travel. Some may be hesitant, but there is truly nothing like traveling.”

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An Inside Look at Digital Nomadism: From Worker to Employer



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