“Listen, Robert, going to another country doesn’t make any difference. I’ve tried all that. You can’t get away from yourself by moving from one place to another. There’s nothing to that.” — Ernest Hemingway

Nearly a century ago, mid-twenties Midwestern freelance journalist and Great War veteran Ernest Hemingway binge-wrote in six weeks the first draft of The Sun Also Rises, a roman à clef about his peripatetic journeys through Spain.

He and his expatriate frenemies were nomadic knowledge workers before “digital nomad” was a phrase applied to today’s itinerant English teachers, startup founders, and yes, freelance journalists.

Source: Wikimedia Commons Originally archived from the JFK library

“The Lost Generation,” as Gertrude Stein dubbed his cohort, lived through technological changes as dizzying and immediately influential as our own. In 1899, the year Hemingway was born, the first long-distance transmission of power flowed from Willamette Falls to a string of lights in Portland, Oregon, fourteen miles away. By the 1920s, telegrams were commonplace, transatlantic travel was cheaper and faster, and the majority of Americans lived in cities for the first time ever.

Source: History Comes to Life, YouTube‌‌

Just as the Lost Generation lived through the psychic disruption of the so-called Spanish Influenza—which killed far more globally than World War I—today’s professionals are still living through today’s novel pandemic. According to Pew, one in five workers worked from home before the pandemic—up to 71% said the same at the peak of COVID-19.

What drives the shift toward a new mode of work in our own era? Will this be a lifestyle that Millennials age out of, or does it represent a more permanent shift in the meaning and location of work? And does moving—to another country, to another role, or to a home office—not make any difference in the end?

The answers to those questions vary according to the nature of the work you’re doing outside a traditional office in 2021. There are three types of contemporary remote workers, all with different temperaments, needs, and future likelihood of success. Let's explore the future of work through the future of the dematerialized workforce.

Take Your Cubicle and Shove It: the Home Office Jockey

The first type of worker untethered from the office is arguably the type with the longest and deepest history. In 1800, at least three-quarters of Americans worked in an agricultural setting. Because work and home were inextricably bound together,“work/life balance” would have been a construct that didn’t resonate. Labor was highly seasonal, and a big draw of emigrating from Europe to the United States was the opportunity for some to acquire their own land.

Over the next hundred years, the typical American acquired more formal education, moved to a city, and was more likely to work for someone else. For the majority, conditions in factories were grim, but for a small population of knowledge workers, cities offered unparalleled opportunities for new forms of socialization.

Source: Our World In Data

For the Man in the Grey Flannel Suit, this shift seems to have disrupted many truths he held to be self-evident. However, even in decades past there were workers in roles where you were less tied to any one employer. Think of the hippie-ish freelance photographers and illustrators in Mad Men: highly educated, urbane young people in touch with what’s going on in the Swinging Sixties in a way that the ad execs were both skeptical of, yet badly needed in their marketing campaigns.


Even Mad Men’s resident psychologist Dr. Faye Miller does not have a traditional office or career—and while undoubtedly a highly paid one, she’s still a consultant.

Speaking of psychology, people drawn to these kinds of roles seem to share a set of traits: highly autonomous and self-driven, less likely to defer to authority and need rigid routines, and a higher tolerance for uncertainty. There’s a reason that so many software engineers have threatened to jump ship if forced back into an office—their work is already highly symbolic and abstract.

Gen Z and Millennials actually want to work in the office more than Gen X, which goes against the stereotype of the young techie unable to navigate office culture. A late-twenties Google software engineer told me that all of the aspects of working at an office I was indifferent towards, he actually very much enjoyed. He was thrilled to be able to go into his Boulder office.

Middle-aged knowledge workers are likely to have the leverage to continue working from their home offices at least part of the time coming out of COVID. After all, Gertrude Stein was essentially a self-employed writer, editor, and tastemaker—and she was fifty when Hemingway brought her his script.

Source: Sony Pictures Classics

#livingthedream: Living by the Fruits of the ‘gram

“It's a funny thing about comin' home. Looks the same, smells the same, feels the same. You'll realize what's changed is you.” ― F. Scott Fitzgerald

The second category is smaller, yet more highly visible, than the first.

Call to mind a “digital nomad.” You might imagine a young woman with a curated Pinterest-type aesthetic, whose YouTube channel evokes an everywoman conversationality paired with a soupçon of wish-you-were-here lifestyle envy. Maybe it’s a guy with a GoPro, selling merch and digital presets, preaching about the liberation of retiring early. Maybe this describes your cousin, or someone you follow on Instagram, and you don’t really know what the hell they do.

When I was an intern at Bucks4Books, a textbook buyback company, my boss Heath told me about a colleague of his who had sold all his worldly goods and moved to Argentina. The story stuck with me, but I didn’t think much about it for years, figuring it was perhaps a phase.

Turns out, it was very much not a phase. Gareth Leonard, the founder of the lifestyle blog Travel Deeper, made the leap after the Great Recession. Gareth makes his living through a combination of selling courses for expatriates, branded merchandise, and corporate sponsorships related to a lifestyle on the road. He has 108,000+ followers on Instagram, who log in for his Travel Trivia Tuesday challenges.

While discussing his business last year during the worst of the pandemic from his (temporary) San Diego home, he told me about some of the challenges of being a road warrior entrepreneur: primarily, the need to feed the maw of the content beast meant he had to pivot to other sources of recurring revenue. He had traded the relative stability of a middle manager position at the textbook buyback store for living in a new locale every year for over a decade. He is, unsurprisingly, unmarried and childless.

However, his passion for his chosen career was obvious. Many are called to life on the road, but few make it their lifestyle. Psychologically, this type of remote worker seems incredibly unlikely to work for anyone else in a traditional 9 to 5. Like all entrepreneurs, they have an extremely high tolerance for risk and an intrinsic motivation to live off the beaten path. As octogenarian feminist pioneer and prolific magazine journalist Gloria Steinem put it in her memoir, My Life on the Road:

“When people ask me why I still have hope and energy after all these years, I always say: Because I travel. Taking to the road—by which I mean letting the road take you—changed who I thought I was. The road is messy in the way that real life is messy.”

The Dematerialized Workforce: New Opportunities, New Threats

Speaking of real life being messy, I am a worker who is part of a third category of remote-first worker, slightly different from either discussed before. Less outwardly glamorous than the globetrotting influencer, but also less financially stable than the engineers and VPs who log in from their suburban home offices.

This New Yorker cover from the Before Times perfectly captures this kind of work-from-nowhere creative class member.


Screenwriters, test prep tutors, yoga teachers, fashion designers, and ESL instructors occupy something of a class and employment no-man’s-land, but they, too, share some psychological and demographic traits.

The terms of their employment are highly contingent: most are contract workers rather than benefited employees and survive gig to gig. Most went to college, but often in the humanities or social science fields, and they are less likely to directly manage others. They are adopters of productivity tools—Slack, Asana, smartwatches—and by necessity often own fewer material things. Some decide to reskill to join or rejoin the more traditional workforce—you see yoga teachers become corporate meditation/mindfulness consultants, screenwriters knock on the doors of Big Tech instead of Hollywood, and pop culture journalists going to Patreon.

Compared to the other groups, this member of the precariat may be more prone to the downsides of an untethered life. Mark Manson, who got his start in the seamy underbelly of pick-up artistry but has since graduated into no-bullshit self-help respectability, self-diagnosed the need to be constantly on the move as an “addiction.”

David Maillet, a self-employed designer living in Mexico City, spoke to me by phone about the pitfalls of this life. Raised in France, he worked in an haute couture fashion house with a view of the Eiffel Tower. However, he felt unfulfilled and eventually landed in East Asia working directly with suppliers. In early 2020, he had a contract with Kmart that was canceled due to COVID shutdowns.

He stresses the need to sock aside a year’s worth of savings if you decide to leave a comfortable job. He believes that it takes an unusual outlook on life—a comfort with not getting validation from friends and family, adaptability to ambiguous situations, and knowing stuff inevitably goes wrong. He believes there is a secular shift in the economy and that many of the “old jobs” simply won't be here in ten years. He used the continental-sounding term “the dematerialized workforce” to highlight the difference between someone like him—in fashion, you are working with bolts of material in one place—and someone like me, whose stock in trade is in ideas.

From Tethered to Grounded: Leaving the Work-From-Nowhere Lifestyle Behind

"When a person spends all his time in foreign travel, he ends by having many acquaintances, but no friends." — Seneca

Partly on a whim, partly out of economic necessity, I gave up my lease in ultra-suburban Draper, Utah, in late April. Pre-pandemic, I had traveled and taken my work with me, but this time I was primarily working (as an SAT/ACT tutor over Zoom).

What others read as adventure, I often experienced as a lack of real stability. COVID was at a low point in the early summer, and I was vaccinated, but I experienced a sense of alienation while living abroad that wouldn’t have been out of place in a Hemingway novel. A lot of the expatriates I met seemed to chiefly spend their evenings at various bars, and the summer months were endlessly rainy. Due to social media, I never truly cut ties from my “old” life and embraced the new one.

I threw my name in the hat for “normal” jobs in EdTech back in the States, and after weeks of interviews, I’m in the final round for the next phase of a more settled, perhaps grown-up existence. I have found my anxiety seems lower, and I am able to more realistically go on dates, with the hopes it will turn into a long-term relationship.

I don’t know for sure where I will end up—maybe Colorado, maybe Hollywood, maybe back East—but I definitely want to work somewhere besides a Starbucks. After hauling a set of too-heavy flannel sheets on a bus back to the spare room I’m renting out for the next 20 days, I miss the illusion of stability my relatively boring life in Draper afforded me. Writing is a craft that requires long stretches of concentration—and a community of people.

Papa Hemingway, through the voice of Jake Barnes, was right about one thing: no style or location of work ultimately lets you escape yourself.

Edited by Rachel Swan