The Dark Side of the Digital Nomad

The following is the original piece I wrote for CNN last year about location independent entrepreneurs, also known as “digital nomads.” Since the whole “Work Online, Travel the World and Live the Dream” angle had been done to death in a million places, I decided to go the other direction and show the dark side of being a digital nomad — the challenges one faces, the emotional pitfalls, the social sacrifices.

Predictably, CNN hated it. The editors hacked it to pieces and asked me to rewrite sections to make it less gloomy. And since they’re CNN and I’m just an asshole with a book about smut, I said OK.

But I was always fond of the original, so I’m posting it here unabridged. Also note: the people and events in the piece are actually composites and mash-ups of my real life experiences and relationships. I did that for the sake of narrative and space. Enjoy.


It’s 12:20PM on a Friday afternoon when most of them shuffle into the hotel conference room. The schedule said 11AM. Wishful thinking.

Floor-to-ceiling windows look out over a rooftop lagoon with the sunny reflective skyline of Bangkok draped behind, 19 floors up.

The people’s feet are adorned with flip-flops and Converse sneakers, some of their bodies in button-downs and blazers, others in cargo shorts and tank tops. They are mostly men, single, in their 20’s and 30’s. But as with every group, there are the exceptions. Eventually 44 of them will fill the full-windowed conference room, bathed in natural light, sipping Singha beer and thirty-cent Red Bulls, listening to ad hoc presentations about outsourcing, systems management, dropshipping, grey-hat SEO, and other esoteric topics.

Unless someone told you, you would never guess that this was a conference for successful internet entrepreneurs and business owners from around the world, that the median income of the scraggly-faced, wrinkle-shirted crowd is likely well into the six-figures. And many of them make most of it while sleeping off their Tuesday night hangovers.

Spontaneous international congregations like this are quickly becoming the norm as more and more entrepreneurs remove themselves from the grid and choose to live nomadically.

In his book The Four Hour Work Week, Tim Ferriss dubbed us the “New Rich”. The idea is we leverage the internet to scale and automate businesses quickly, and then we leverage our location independence to create a greater wealth of experiences through travel and adventure rather than collecting material possessions.

For a group of people spread all over the planet, the New Rich paradoxically run into each other quite often. We’re highly networked online and we all have a penchant for landing in the same handful of locations.

There are the start-up incubators: groups of green internet entrepreneurs who come together in an affordable location to live together and help each get their projects off the ground. Southeast Asia is ground-zero for many of these incubators due to the rock-bottom cost of living and high quality of life: Chiang Mai and Bangkok in Thailand, Saigon in Vietnam, Bali in Indonesia, Cebu in the Philippines and also more recently Medellin in Colombia.

Then there are the entrepreneurs bent on cashing in on emerging markets – countries and cultures which are maybe 5-10 years behind the curve in terms of internet sophistication and market saturation – ambitious Western entrepreneurs swoop in to take advantage of the opportunities in places like Buenos Aires, Sao Paulo, Beijing, and Kiev.

Then there are the conferences, the meet-ups and the masterminds, a smattering of which are organized across the world in places like Las Vegas, Berlin, Tokyo, Miami and now Bangkok.

The social life of the New Rich is bizarre. The line between business networking and friendship is non-existent, as the handfuls of people on the planet who can relate to your lifestyle also happen to be possible joint venture partners and/or clients. Conversation and support is always a blur of intentions.

Fuck the scenery, I've got emails to check.
Checking email, like a boss.

The other strange aspect of this lifestyle is that the people who you are most connected to and relate to the most, you only see a few times a year. The last time I saw my best friend (who is location-independent as well) was last December in Guatemala. And before that I saw him in Singapore in October. Before that he visited me in Thailand in August.

But there are some friends who you never actually see.

Sitting at the table with me is Jay. I attended one of Jay’s webinars a few months prior and recently hosted him on one of my site’s podcasts. He also briefly lived in Bali with an SEO expert I was friends with in Colombia. Despite “knowing” Jay for six-plus months and strategizing about our businesses regularly, I have never met him until today.

Also with us is Tom. Tom is American and a top-dollar online business consultant who lives in the Philippines and is now mentoring one of my friends back home in Boston. Tom and I and half a dozen other entrepreneurs are members of a mastermind group that hold weekly hour-long calls together where we discuss our businesses and our lives. Despite speaking to Tom weekly for the better part of a year and asking and answering each other many personal questions, this is the first time I have met him in the flesh.

And yet this feels normal now. It doesn’t occur to any of us that almost none of us actually know each other. We run in the same private forums and are members of the same email lists. We all know someone who knows someone who knows someone. And we’ve all cut our teeth building our businesses while living in the same half dozen or so places around the world. Yet we don’t know each other.

We can relate on a deeply experiential level. In a lifestyle where none of our friends or families back home can comprehend what our day-to-day is like, these loose global networks exist for us to keep each other sane.

Yet, for our philosophical connections, we lack that emotional depth and bond that comes with shared struggle and life’s important moments. Mainly because there are few struggles and when the important moments happen, we’re always somewhere else.

One successful entrepreneur, in a rare moment of vulnerability, recently wrote that he burst into tears in a small suburb in Japan watching families ride their bikes together in a park. It struck him that this simple, mundane pleasure was something he would never know again. On my annual short visit home for the holidays, my mom asked me with disappointment in her voice, “Am I ever going to see you for more than a few days each year again?” I didn’t have a good answer for her.

The nomadic lifestyle seems to bolster some egos and bruise others. I credit it with building my confidence and self-esteem. Looking back, I was obsessive and desperate with my habits and relationships back home. Being put in country after country where nobody knew me and nobody cared who I was did me a lot of good. I let go of a lot of baggage.

But for others, it’s the opposite. There are plenty of vices one can freely indulge in in the world, especially in developing countries. And when you’re constantly the center of attention for everything you do and every choice you make, one can fall into a quiet narcissism without even realizing it. I’ve seen it. And it sucks. Or as another nomadic friend recently said, “Some people are better off without this lifestyle. It’s too easy to disconnect. It’s too easy to obsess about yourself. I’ve lost a few friends to it.”

To many back home, we are living the dream. We have access to an unspeakable freedom of choice and boundless personal opportunity. There are few limits. Last year I visited 17 countries. This year I will visit 10. Last year, I saw the Taj Mahal, the Great Wall of China and Machu Piccu in a span of three months. I hiked a volcano and a glacier 2,000 miles apart in the same week.

Only picture I have of myself at the Great Wall of China. Was by myself and freezing.
The only picture of me at the Great Wall of China. I was by myself and freezing.

But I did this all alone. Just me and sometimes a few anonymous faces – acquaintances of mutual travel convenience. My life is awesome – no, really, my life is fucking awesome. It just needs a parental advisory sticker. Because the price of overwhelming freedom is often my isolation.

Back in the conference room in Bangkok, new contacts are made, business ideas are born, and online connections are materialized. A series of agreements to meet up and hang out are made – a pair who will be in Barcelona around the same time agree to email each other; a sub-group mulls over meeting in Berlin next Spring.

For a group of people who all fight the silent battle of loneliness, we sure are fickle with each other. But when you have so many opportunities before you, it’s easy to avoid commitment, even to a friendship. Many of the people and places become interchangeable and you begin to wonder if that’s just because of the traveling or if that’s all human relationships and you just never noticed it before.

Don’t get me wrong. I’m not complaining. I’ve loved every minute of this lifestyle. But there are real, tangible, social and emotional tradeoffs involved. I wouldn’t trade it all for the world because I already did trade it all for the world. Because the world is a pretty badass place. For a while.

Economists say there is no such thing as a free lunch. I say there’s no such thing as a free life. Some of us just learn to choose better shackles than others.

I look back to the skyline, past my Singha-swilling contemporaries. It occurs to me that the New Rich, for all of our impressive values, are just as guilty of materialism as the old rich, it just takes a different form. Instead of an addiction to status and possessions, we are addicted to experience and novelty. And the end result is the same. Our relationships, our connections to what’s real, sometimes suffer. And for the first time in three years of non-stop travel, I quietly wish for a home.

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