The World’s First Digital Nomad: Steven K Roberts – A Pioneer

Long before remote work went mainstream, one digital nomad pioneer blazed a trail across the US on a custom-built bike, with a computer bolted to the frame. In this exclusive interview, One Planet Journey founder Richard Lindberg has a deep conversation with Steven K Roberts, the world’s first digital nomad. Steven shares how his journey in the 1980s foretold today’s work-from-anywhere revolution. Discover the roots of digital nomadism, its evolution, and why his story still matters today. If you’ve ever dreamed of combining work, freedom and deep travel, this is where it all began.

The Growth of Digital Nomadism 

The digital nomad movement has shifted from fringe to mainstream. What began as a subculture of backpacker-bloggers and remote tech workers has grown into a global lifestyle embraced by millions. As of 2024, over 35 million people worldwide now identify as digital nomads, contributing approximately $787 billion annually to the global economy. The United States alone accounts for over 16.9 million of these individuals (twoticketsanywhere.com). Enabled by technology, remote work, borderless banking, and flexible visas, this new wave of professionals want more than travel. They redesign their lives around freedom, curiosity, and purpose.

This lifestyle aligns closely with the concept of deep travel, where people seek meaningful, immersive experiences that foster genuine connections with destinations and locals. Digital nomads often spend extended periods in one location, allowing them to delve deeper into local customs, traditions, and daily life, enriching both their personal and professional journeys.

Yet the nomadic path isn’t all turquoise waters and Instagram reels. Staying productive while changing locations, maintaining deep relationships without fixed roots, and navigating visa restrictions or burnout are some of the real-world challenges that come with the territory. At the same time, a growing ecosystem supports the lifestyle: co-living hubs, slow travel communities, and government schemes from Portugal to Indonesia that welcome long-stay, high-skill travellers.

A Digital Nomad Pioneer 

Tsugio Makimoto and David Manners popularised the term “digital nomad” in their 1997 book, Digital Nomad, where they envisioned technology enabling a return to nomadic lifestyles. To understand where this movement began, and how far it has come, we need to go back over forty years. Long before Wi-Fi, coworking spaces or digital nomad visas, Steven K. Roberts set off on a 10 000 mile journey across America on a recumbent bicycle packed with solar panels, radio gear, and a primitive computer.

In the early 1980s, he left behind a conventional life to live and work on the road, writing articles and books from roadside diners and strangers’ porches. Many now see him as the world’s first digital nomad, pioneering the lifestyle long before the term existed. We caught up with Steven to hear his remarkable story, equal parts adventure and foresight, and reflect on what it means in today’s hyper-connected world.

What sparked your idea to combine tech with travel in such a pioneering way? 

I lived in Columbus and sometimes joked that the city inspired long distance travel. In truth, I had always had fantasies of going off on grand adventures, but reality got in the way. When I turned 30, I worked on things I didn’t much enjoy, to pay for stuff I didn’t really want. Like a house in suburbia with a mortgage. I wanted to combine all my passions into a lifestyle, and during my travels to trade shows and conferences, I often met amazing people who inspired me. Academia, cool companies, famous writers, or happy folks living good lives in different forms. It made me desire to be free to explore alternatives and not turn cranks to keep the overhead paid.

The Birth of a Digital Nomad Pioneer 

With this noodling around in my head, trying to find a realistic solution that involved travel, one day I went on a local bike ride with a friend. We met an old man on a recumbent bicycle and while I had certainly heard of these bikes, I had never actually seen one. Kindly, he let me try it, and an image formed in my head.

If I could combine a comfortable high-tech bicycle with one of those newfangled portable computers that had just come out. Then add some kind of net connection, another brand new technology (CompuServe sat right there in Columbus), a solar panel to power the equipment, and a base office manager to tie it all together. All in all, I should be able to take my freelance writing and consulting business on the road. Physical location would be irrelevant. 

The idea gripped me and absolutely would not let go, for this suddenly seemed like the way to unlock all my unfulfilled fantasies. That night, I stuck a for sale sign in front of my house and spent the next 6 months in obsessive preparation.

What challenges and surprises did you encounter? 

It’s fun thinking back to those times. Unfortunately, the trip didn’t magically cure bad work habits. Days and weeks would pass with deadlines looming, me too busy with the adventure itself, meeting people, and logistics. Of course, it didn’t translate into independent wealth, but no surprises there. It stressed me for the first few months. 

Personal challenges, something I called “the chronic loneliness of passing through,” manifested. When all interactions have beginnings and endings, life becomes a succession of show and tells, new connections, and goodbyes. I don’t know what I would have done without CompuServe, which gave me a sort of enclave of stability. It became a strong sense of continuity even as my reality completely changed day to day. I learned to have fun with this, and it formed a huge part of the adventure.

For sure, I had endless technical challenges and learning curves, but I never really thought of it as a problem.

How did you balance connection with the freedom of being on your own? 

The need for connection and freedom turned out to be an absolutely magical moment of transition in society and technology. In 1983, CompuServe had just happened, and it quickly became my hometown. A place for chats with groups of friends or more formal conversation focused on subjects. My readers replied to my stories, and I kept up email correspondence, etc. 

I loved the strong continuity it provided while wandering freely in physical space. It even extended into romance and the development of close friendships with people I had never met. It’s fun to look back now 40 years later and remember how utterly special it was. 

What is freedom to you? 

A recurring theme in the adventure took the form of freedom versus security. Initially, I expressed that in terms of relationships, but it quickly became clear that most aspects of life fit on that spectrum. I built myself the tools to stay free while still ensuring that I had business, connection to home base, cultural stability, and so on.

All this became a defining part of the pioneering digital nomad lifestyle, and something that I would often mention in interviews. It enabled me to take risky choices that I never would have imagined otherwise and somewhere along the way I noted that the greatest risk is taking no risk. Without that mix of freedom and security, I’m not sure I would have had the audacity to do such things. 

Of course, one person’s freedom is another person’s absolute instability and high-risk endeavour! But for that epoch in my life, I relished a good combination. 

What gave you the deepest insights into yourself or the world around you?

Getting rid of a lot of my cultural stereotypes and fears, and that if you think too much about where you’re going, you lose respect for where you are.  

At the beginning, I got excited about state lines and thousand mile marks, fascinated by meeting people, and fine tuning technology. Sometimes I think I flew through places without really seeing them clearly, my focus still quite local.

Over time, that changed, partly because the novelty of being on the bike wore off and it moved from foreground to background. But also remember writing about it, not only retrospectively as a book but ongoing as what we now call a travel blog (but didn’t exist then). It felt like a distillation of life, presenting lots of evolution and growth in a shorter amount of time.

How has your vision of travel, technology, and humanity changed over time?

We’ve had quite an evolution of all of those things, with technological factors amplifying everything. Back then, part of the adventure was the pure geek novelty. This whole thing about hooking up an acoustic coupler to a payphone and connecting with somebody far away. How crazy is that? And while doing it, some local would come over and peer over my shoulder, ask questions, and invite me home for dinner.

Now they’re part of the environment, and the less we are aware of them, the better. We have unfettered connectivity, including video, live tracking, and insanely huge storage spaces that weigh essentially nothing. And wherever that’s applied, especially in an intrinsically mobile life, it is a complete inversion from what I lived during those years on the road. The cultural component of that is not insignificant, since using these tools to be a tech nomad is not in itself at all unusual. 

I used to joke that someday I would get lots of media coverage by doing a cross-country bicycle trip without a computer. The reporters would call it amazing. How do you get your email? What about blog posts and weather predictions and keeping a sense of community? That’s so heroic.

How do you see deep travel evolving in tandem with remote work and digital nomadism? 

I think the big evolution is freedom to make deep travel choices, once remote work eliminates time constraints on the typical traveller budget. It takes holiday schedules out of the equation and is completely liberating. My own travels had that flavour. I found it weird meeting people who tried to cram a cross-country trip into a short period of time. I even wrote about one such encounter with guys I met in Florida. They had drawn a line across the United States and picked the roads closest to it, and knew what day they got to see the Pacific. It mystified me. 

I think the nature of travel can change as much as somebody wants it to once they have fully decoupled.

How should travellers combine their work with a deeper, more meaningful journey/lifestyle?

Certainly keep enough headspace to develop in whatever way you want, not getting burned out by the time you get the chance to focus on it. Travel is particularly lovely because it can take any form at all. And of course writing is a license to be a generalist. So that particular combination worked really well for me. But in the broader sense, people doing other kinds of work like web design, should be able to benefit from the same kind of dynamic. Stimulating travel life with windows of opportunity to sit down and crank out projects. 

My advice is to get on with it before you get any older. I used to joke about this and loved getting thumbs up from old geezers who told me I did the right thing to do it at a young age. But I didn’t feel wise at all, I just had fun! But now, in retrospect, I know for a fact that I would not be doing it at my current age. Too many things hurt, too much complexity, insane to do lists, accumulated tonnage. No way would I feel mentally liberated enough to go have an open-ended journey while somehow making a living. 

Are there current projects you’re working on that connect with your past journeys? 

For about 25 years, I’ve said I need to get a book out. This is too large of a project with all the other things that I’m doing, and I briefly considered doing it as a video. Although that’s even more work, and a whole new kind of learning curve. So, I took a more realistic and deeply familiar approach. I started a Substack to do weekly posts from the adventure itself, mostly taking the form of book chapters with added commentary about technology, cultural notes, photos, and videos.

Another current project is on a whole different scale and has a mobile cache, although realistically it’s not moving around much. I have a 48 ft media digitising lab packed with geeky systems for handling everything from old home movies to videos, audio reels, slides and negatives, and so on. I do like having a mobile lab, but things need arranging to go trundling down the road just yet! Still, it feels connected to the old days.

What are some favourite places from your travels?

That’s a tough one. It depended on what fascinated me at the time. I remember feeling particularly enchanted by places that looked like home. When I found sweet little towns where I fit in and people had a sense of community, they affected me strongly. 

And of course this sounds like a total cliche but I also love beautiful destinations, beaches, gorgeous winding mountain roads, roads with nice shoulders and low traffic, and all those other things that bicycle tourists live for. I like edges between land and water, spots with contrast that attract interesting people. 

But really I think community is probably the strongest for me, and of course that covers a wide range because some of them are seasonal and others are like a cosy old couch. Some get stepped on and changed forever by too much money, tourism, second homes, enlarged airports, and corporate commodification.

The Future of Digital Nomadism 

Steven K Roberts didn’t just invent the digital nomad lifestyle, he pioneered what was possible. Long before hashtags, co-working and digital nomad visas, he chased a question that still resonates: What does it mean to be truly free?

Today, the term digital nomad conjures images of laptops on tropical beaches. But Steven’s journey reminds us of something deeper. A return to intentional mobility. His lifestyle forecasted the values many digital nomads now chase: the blend of autonomy and connectivity, the pursuit of meaning over material, and the radical act of designing a life not confined to postcodes or clock-ins.

He saw early how remote work could unlock deep travel. Instead of counting countries, you inhabit moments. Steven’s pioneering journey anticipated the desires that drive today’s digital nomads. The ability to work remotely has allowed them to immerse themselves in destinations in ways tourists never could. With the rise of flexible work environments, the barriers to becoming a digital nomad are lower than ever. If you’ve been waiting for the “right time” to go, take Steven’s advice. Get on with it.

Steven’s Top Recommendations for Today’s Digital Nomads:

Presence: Don’t rush through the world. Absorb it.

Community: Prioritise authentic connections.

Balance: Work should complement travel, not overshadow it.

Act: “The greatest risk is taking no risk.”

Curiosity: Be open to changing your mind, your tools, and your route.

Have you tried digital nomad life? Which locations have you lived and worked in? Let us know in the comments. Subscribe to our newsletter and benefit from travel guides, sustainable tourism and luxury travel tips, insightful interviews, and inspirational places to visit. One Planet Journey – The World’s First Deep Travel Magazine.