The Paradox of Loneliness in the Digital Nomad Lifestyle

It was an hour into the ferry crossing from Santorini to Athens, Greece. But I couldn’t peel myself away from the back of the ship, despite the wind and sea spray stinging my skin. The once towering cliffs of Oía morphed into a faint gray outline along the horizon, almost imperceptible now against the dawn sky. I gripped the cold metal railing, still wet with dew, and took a deep breath of salty air. “This is uncomfortable,” I thought, in many respects.
I was sailing away at will from the friends I’d made over the last couple months. Away from a sunny island utopia where — hours earlier — we were zipping around on mopeds without a care in the world.
The fun, laughter, and lightness of the past weeks suddenly collapsed into the weight of loneliness and isolation. I was alone on the deck of this ship, but also in the world. I knew this feeling all too well. It’s a particular sense of separation mixed with sentimentality. Detachment from a place, people, or potential life. A longing for roots without necessarily losing momentum.
You see, I don’t have a home.
I’ve been location-independent for over a decade. Today, I happen to be on a ferry, making my way through Athens to Bulgaria, my base for the next 3 months. Another place to peel myself away from when the time comes. In this case, my most recent comfort zone involved the digital nomads who I’d been traveling with for over a month.
We started as a group of 250, then 100, then 50. Our pseudo-family dwindling little by little. Going our separate ways. And now there was one. Me.
You can’t pin a nomad down.
I felt overcome with emotion, but not necessarily sadness (smile that it happened, right?). It was more like a release of adrenaline from the entire experience. Two days earlier, someone asked me during a Facebook live:
How do you deal with loneliness as a digital nomad?
I said I rarely felt lonely. Until, ironically, at this very moment. It got me thinking that loneliness is a perception. It’s a mirage. It’s malleable. The opposite of loneliness is the subjective feeling of being accompanied — something we can convince ourselves of in the moment if it suits us.
Can we trust that this (or any) feeling is real? I’m not sure. It stands to reason that feeling lonely comes as a result of being physically alone.
But haven’t you also felt lonely while being surrounded by people?
Loneliness can creep up and hit us at any time. I felt lonely on my birthday last summer, standing in the middle of the biggest club on Italy’s Amalfi Coast, celebrating with 100’s of people. I’ve felt lonely while laying in bed next to my partner of many years, still missing him whenever I was away. I’m feeling lonely on this ship, after specifically craving some alone time.
Curiously, I’ve never felt more whole and connected to universal existence than during the times when I’ve been utterly alone. Such as: hiking in the Pacific Northwest, walking for days on the Camino de Santiago, or whizzing through Amsterdam on my bike in the middle of the night. In fact, I’ve experienced consecutive months of sheer, uninterrupted bliss while traveling alone — all the while without feeling lonely.
Yet the fear of being alone is one of the main reasons people hesitate to start traveling long-term. There’s an assumption that staying close to home will somehow stave off this loneliness. People confuse familiarity with comfort, while at the same time traveling to “get away from it all.”
It’s perplexing. The human experience can seem contradictory and impossible sometimes.

By now, all I can see in the distance is the deep blue of the Mediterranean Sea. But it looks much different than it did on my way here. I recall that water’s color, texture, and demeanor are in constant flux depending on the wind, weather, and light. So too is our individual perception of what’s going on in our inner and outer worlds. Feelings pass through the human psyche like the waves I’m looking at, then dissipate as if they were never there.
The average person experiences tens of thousands of thoughts every day. So instead of trying to avoid a particular state or emotion — we might welcome it, look at it, and try to learn from it.
One thing that always puts me at ease in life is remembering that emotions are universal. This common thread connects us with the other human beings on the planet, regardless of physical distance. It allows us to feel empathy for one another while maintaining our individuality. The presence of others is always around us — in body or in spirit.
In that sense, we never have to feel lonely at all.






