A Brief History of Digital Nomads

Excerpt from the new book Global Natives

Hey, Every readers! We’re excited to share this exclusive excerpt from a new book on digital nomads, Global Natives: The New Frontiers of Work, Travel, and Innovation, by Lauren Razavi. Lauren has been nomadic since 2013 and currently works at the Y Combinator company SafetyWing, where she leads the Plumia mission to build an internet country for digital nomads. 

This excerpt is a fun dive into the technology and ideas that led to the rise of work from anywhere. For more on digital nomads, remote work, and borderless living, subscribe to Lauren’s newsletter, Counterflows, and follow her on Twitter @LaurenRazavi. And don’t forget to buy a copy of Global Natives—you can even read right away online.


Portable Technologies 

In March 1983, a recently-formed technology company called Compaq Computer Corporation shipped an exciting new product: the world’s first portable computer, the Compaq Portable

Despite a price tag of US$3,590 (equivalent to around US$9,500 today), the model sold upwards of 50,000 units in its first year. This beast of a machine weighed 28 lbs (13 kgs) and folded up into a luggable case the size of a portable sewing machine. Crucially, it was designed to be taken as carry-on luggage. The tech journalists loved it. 

In 1982, PC World Magazine ran a cover story titled “Traveling with the IBM PC’s First Portable Competitor.” It  might just be the first portrait of the work from anywhere movement we know today:

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When this image was shared on the r/digitalnomad subreddit in January 2021, it garnered 1.1K upvotes and a 98% rating, meaning that almost everyone who saw it gave a virtual thumbs up. In today’s context, the scene feels familiar. We’ve all seen Instagram posts from social media influencers sitting by the pool or the ocean, a tropical drink beside an open laptop, living the dream and ignoring the screen glare. Whether the images are honest or not, the concept of combining work and play in paradise has been an aspiration since before the Compaq hit the market.

While the definition of “portable” has changed a lot over the past 40 years, the recognition that technology would uncouple work and location—challenging the foundations and certainties of 20th-century society in the process—has been clear for decades. Every generation has thinkers and tinkerers who dream of connecting seamlessly across borders, locations, and time zones—and some go the extra mile to articulate what that world might look like. 

As far back as the 1960s, the science fiction writer Arthur C. Clarke predicted the emergence of global remote work, speaking specifically about nomads working from Bali in the 2010s. Fifty years before I arrived in Ubud, Clarke had anticipated the presence of people like me in that part of the world, using digital tools to do exactly what I was doing. 

 

The earliest digital nomad, though, wasn’t equipped with a smartphone or even a laptop. Between 1983 and 1991, Steven K. Roberts traveled 17,000 miles across America on a bicycle. He was working as a tech writer in Columbus, OH when one day it dawned on him that he didn’t much like his city or his expensive lifestyle. So, he sold his house and left.

Roberts wasn’t just a nomad—he was an inventor, too. When I spoke to him for this book, Roberts talked about hacking together his custom bike with a four-button keyboard and LCD screen on its handlebars. Solar panels, connected to batteries, powered everything but the wheels: "I carried a RadioShack model 100 laptop, 5 watt solar panel, and had an account on CompuServe that I used to communicate with my base office," he told me.

With this admittedly janky tech setup, Roberts could now work while he cycled. He spent eight years living as a nomadic freelance writer. His bicycle received various upgrades over the years, ultimately becoming an object worth $1.2 million by 1991. Today, it resides in the Computer History Museum in Mountain View, California. Roberts’ pioneering journey was an early experiment in a new way of living, made possible by portable technologies. 

Just a few years after Roberts completed his journey, “digital nomad” entered the lexicon. The term originated in a 1997 academic textbook of the same name, by Tsugio Makimoto, a celebrated Japanese technologist whose contributions to the field of computer science earned him the nickname “Mr. Semiconductor.” The author’s note in the front of the book summarizes its main argument:

“Times are changing. The driving force of change in the world is technological advance. It is pushing in two directions: towards smaller, cheaper, more portable personal tools, and towards the imminence of cheap, high capacity, global communications networks. 

Technology does not cause change but it amplifies change. Early in the next millennium it will deliver the capability to live and work on the move.

The world’s major technology companies are targeting the lifestyle of the ‘mobile professional’ in developing the tools for leading a nomadic business life. In time these tools will become cheap enough for everyone, and the biggest lifestyle change for 10,000 years – since humans stopped being nomadic and settled down to farm – will be delivered to most people in the developed world. 

People will therefore be able to ask themselves, ‘Am I a nomad or a settler?’ For the first time in 10,000 years that choice will become a mainstream lifestyle option.”

When Makimoto wrote this in 1997, the technology environment was a little different than today. It was the year DVD players were sold commercially in the US for the first time, at a cost of $599 to $750 per unit. The first-ever Grand Theft Auto game had just shipped on Playstation 1, the MP3 file format was newly invented, and AOL was rolling out unlimited web access for $19.95 per month. 

If Makimoto was right on the trend—and he was—he was off on the timing. Technology did advance to make remote work and global communication possible in the early part of the 21st century, just as all the futurists and technologists had predicted, but real-world enthusiasm for this way of living developed at a slower pace. While the technologies for a nomadic life would emerge within a decade of Makimoto’s Digital Nomad, the wider cultural shift to embrace them was slower than predicted—the 2010s rather than the 2000s.

The lesson here is that tools often move faster than people. The ability to do something on a technical level doesn’t mean it’s destined to become a lifestyle movement. For that to happen, people first need a human character to represent whatever the new possibility might be; to make it feel more real. In 2007, a book provided exactly the right mix of ingredients. With its release, the face of modern nomadism would emerge—and usher in the beginning of location-independence as a 21st-century subculture.

From Vision to Subculture

If you were in Silicon Valley in the early 2000s, Tim Ferriss needs no introduction. He is, after all, the person who won, by a huge margin, Wired magazine’s “self-promoter of the year” by public vote back in 2008. You might have encountered him at somebody else’s party, distributing copies of his five bestselling books. Or maybe you’ve come across his blog, YouTube channel, or podcast, where he interviews the crème de la crème of entrepreneurship and entertainment: Marc Andreessen, Jimmy Wales, Margaret Atwood, Hugh Jackman, Malcom Gladwell, and Amanda Palmer.

Ferriss’s first and most popular book was The 4-Hour Workweek: Escape the 9-5, Live Anywhere, and Join the New Rich, published in 2007. Its core argument is that people should design the life they want and see the world now, not work in a soul-destroying job and wait for retirement to really live. In popularizing this idea, Ferriss piloted and promoted a new philosophy of life and work—one that has been simmering away in the background ever since. This notion of exploring the world and enjoying the good life became digital nomads’ guiding principle, and a global subculture of people began pursuing remote businesses, blending work and travel in new ways. 

The same year The 4-Hour Workweek was published, Steve Jobs unveiled the first iPhone. Facebook was three years old, and though it already had 14 million users, its addictive qualities were not yet so expertly tuned. (For context, 2.8 billion people now use Facebook at least once a month.) Twitter had been around for just a year, a niche microblogging site populated by the small, fascinating subset of early adopters who still wear the “joined in 2006” badge on the platform today. YouTube was in its terrible twos, blubbering and buffering its way toward relevancy. Instagram, and the shiny influencer culture it is known for, had yet to be invented.

The mainstream internet may have been in its infancy, but the tech builders of Silicon Valley could see what was coming just as well as their predecessors had: all the tools necessary for people to work from anywhere conveniently, affordably, and effectively. Ferriss was a prolific networker in the Bay Area, detecting those same signals as he wrote The 4-Hour Work Week. But would anybody choose to use their ever-thinner laptops and fancy new smartphones to actually do this? Or would “running away to Bali” just be something Californians excited themselves about at acid parties?

Enter Ferriss. In an environment not yet so saturated by the internet, he emerged as a self-help and “life hacking” guru, selling an alternative path to a familiar vision of success. He made a career out of teaching people how to think about money, harness their productivity, and be their “best self.” In the world according to Ferriss, these things are all simple to achieve—you just have to want them. 

Millions of people bought into Ferriss’s philosophy, though far fewer took action in their own lives. Ferriss offers himself up as the guinea pig for every action he tells others to take. In doing so, he becomes his audience’s yardstick to measure themselves against: If he can do it, what’s stopping me? Through his blog, Ferriss made people feel like he was sharing insider knowledge—your successful friend who spills their secrets over dinner and a few drinks. He took ownership of the “self-experimentation” genre, and achieved astonishing success. 

In the years following its release, The 4-Hour Workweek slowly spawned a movement of location-independence. To fund their adventures, Ferriss recommends his followers design a “low-lift” business. In this kind of venture, the owner has simplified operations sufficiently that it’s possible to minimize the hands-on work while also maximizing profits. The business itself can be anything. The approach is what’s important. Ferriss suggests readers do as he did and start a dropshipping company, buying cheap goods from manufacturing hubs like China and India, and using the internet to sell them to wealthy consumers in the West. 

Ferriss’s own dropshipping business was that most noble of endeavors: a sports supplements brand. He founded BrainQUICKEN in 2001; by the time he sold the company to a private equity firm for an undisclosed sum in 2010, it was known as BodyQUICK. In The 4 Hour Workweek, Ferriss claims he was able to reduce his working hours at BodyQUICK from 80 per week to just four. (Notably, friends and colleagues say Ferriss works many more hours than that each week as an author, podcaster, YouTuber, speaker, entrepreneur and investor, and has done so every single year since The 4 Hour Workweek was published.)

Many people arrived on the ground in a faraway country, however, and decided to skip a step. Rather than following Ferriss’s entrepreneurial path, they used the internet to create online courses and digital learning materials to aid others in becoming digital nomads. Some developed educational products on how to build a dropshipping business, despite never having done it themselves. These people aspired not to the “low-lift business” part of Ferriss’s vision, but wanted to become self-help gurus instead—often without embarking on the “self-experimentation” path at all, unless buying a plane ticket counts.

In the late 2000s and early 2010s, a lively cottage industry of course creators, virtual teachers, coaches, bloggers, and event organizers sprung up. A 2014 study of nomads by Harvard Professor by Beth Altringer suggested that most of them didn’t earn enough to do well. This creates something akin to a multi-level marketing or “pyramid” scheme like Avon or Herbalife. These nomads’ finances rely almost entirely on converting others to the lifestyle. It’s a trend that persists to this day.

There has always been tension between the “social media nomads” and the rest. Aspirational content about nomadism is many people’s entry point to the movement, though it’s not representative of most nomads’ activities, intentions, or experiences. As a frustrated participant in the Harvard study put it: “They post pictures of themselves lying around on the beach, and then my clients start thinking I’m less reliable if I’m a digital nomad.”

The trend of nomad-influencers is a highly visible manifestation of Ferriss’s worldview, inviting would-be nomads to see the world as their playground and prioritize individual gain over everything else. Ferriss encourages his followers to leverage global currency and cost differences in what he calls “geo-arbitrage,” short for geographic arbitrage. The calculation is simple: If you’re earning a New York or London salary, your money lasts longer and buys you more away from those locations: tropical climates all year round, modern apartment buildings with gyms and pools, and varied, affordable dining options.  Of course, there’s nothing wrong with wanting to travel and improve your lifestyle, but the very concept of geo-arbitrage highlights the stark inequalities between people born in different countries. 

Ferriss also uses virtual assistants, usually located in much poorer countries, to stay on top of his admin work and anything else he doesn’t feel like doing. When asked about the ethics of outsourcing undesirable tasks to cheaper markets in a 2011 interview with The New Yorker, Ferriss said: “There are people I have outsourced to in India who now outsource portions of their work to the Philippines. It’s the efficient use of capital, and if you want the rewards of a free market, if you want to enjoy the rewards of the capitalist system, these are the rules by which you play.”

Ferriss’s perspective is perhaps easy to grasp if, like the majority of early nomads, you are male, white, wealthy and American. Of course, most of the world is not. But that point doesn’t get addressed in The 4 Hour Workweek. To look at all of this as a game is a pleasure enjoyed by folks with the right passport, born in the right place, at the right moment in history. Ferriss does not acknowledge the passport lottery he won, nor does he dwell on the matter of geo-arbitrage only being possible for some. 

 

Still, the book was the catalyst needed for the ideas of work from anywhere to move beyond being possible and become desirable. Without a character like Ferriss to slot the components of global remote work together, showing what our lives could look like, digital nomadism may have remained the quirky fascination of fringe futurists for another decade. Instead, there was now a guide and a guidebook—and it was a bestseller. 

But it wouldn’t be long before Ferriss’s ideas were remixed with new values.

The Birth of Nomad List

In April 2013, an MBA grad named Pieter Levels, then 27, sold all his stuff and set off from the Netherlands to travel the world. 

A few years earlier, when Levels was studying at Rotterdam School of Management, he accidentally launched his first online business. He uploaded electronic music mixes to YouTube and his channel, Panda Mix Show, quickly took off. By the time Levels graduated in 2012, he was making $2,000 per month. A friend commented that this income meant he could live “pretty much anywhere.” He’d already spent six months studying abroad on an exchange program as a teenager, so the idea of going overseas didn’t faze him much. Plus, he was curious to see if he could maintain an income on the road. 

Over the next few months, Levels got rid of everything that didn’t fit in his backpack, then boarded a one-way flight to Thailand. He kept hearing about The 4-Hour Workweek, but assessed that the business of dropshipping was “bullshit” and definitely not his scene. 

Yet being a YouTube music star wasn’t quite right either. For Levels, modest success on a third-party web platform, especially one owned by a global tech giant like Google, didn’t spark joy. He wanted to build something of his own—a different, more independent kind of online business. A self-taught coder, he decided he would launch 12 startups in 12 months while he traveled from place to place. These “startups” would be bootstrapped, built entirely by Levels, and have no outside investors. By the end of the experiment, he figured he would probably have come up with a longer-term plan.

Like many nomads at the time, Levels soon ended up working out of Hubud in Bali. There, he wrote the first lines of code for his seventh startup, Nomad List, a website that ranks cities according to their suitability for remote workers. The site uses APIs to curate data sets and convert them into an attractive user interface that updates in real-time. Its gimmick is perfect for the FOMO generation: the home page reveals the best place in the world for nomads to be at any given moment. Between 2014 and 2017, as the site and interest in what it offers grew, Levels became the poster child for digital nomads as we now know them. Media brands from Wired to the BBC to CNN ran stories on nomads, and Nomad List became both a resource for and a symbol of a new global subculture.

Levels took Ferriss’s lens on the world and remixed it with maker values. Yes, nomads wanted to leverage their location and mobility, but there was a bigger picture too. They want to make an honest living, learn by doing, solve real problems, and create things of value. Levels’s interest was in bootstrapping, not dropshipping, and as he put it in his book, MAKE (2018), “Having some positive influence on people's lives is a lot more interesting to me than more revenue.” The rising nomad movement wasn’t just about profit and pleasure as Ferriss’s marketing suggested—it symbolized a new understanding of what was possible in a globalized world. Rather than waiting for the fruits of globalization to trickle down to individuals, nomads went ahead and globalized themselves, embracing the popular mantra: “Ask forgiveness, not permission.” 

Depending on who you ask, nomads represent everything that's right about globalization or everything that's wrong with it. For generations, people have traveled to exotic and lower-cost destinations, tempted by the weather, low living costs, and opportunity to experience new cultures. At its most optimistic, the nomad movement could be viewed as a chance to build bridges between emerging and established economies. But since nomads mostly hold the powerful passports of former empires, some say they are following in the footsteps of their predecessors to travel, adventure, exploit, and even colonize, with little concern about their impact on host communities. 

Digital nomadism works best for those in a position of privilege who can already afford to buffer its risks. So, what does it mean if knowledge workers from wealthy countries work remotely in poorer countries, and climb a few rungs up the class ladder compared with the local population? Enjoying the fruits of an “exotic” setting while taking advantage of global inequalities like cheap labor, currency discrepancies, and low property prices raises questions about the structures the nomad lifestyle is built on and supporting. 

Trade, capital, knowledge, and communication all flow freely across borders, yet humans themselves still face restrictions. While a person’s rights are still determined by their passport, the old systems of wealth, power, and status will persist in the world. The legacy infrastructure governing mobility, residency, and taxes has not caught up with the way people are living. Instead, we’re stuck with a global system optimized for inequality, and which privileges and restricts people based on their birthplace, heritage, physical location, skin color, and native language. As work from anywhere goes mainstream in the 2020s, can we really rely on trickle-down equality to achieve more equitable outcomes? 

Keep reading Global Natives at Holloway.

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