Solo Travel as a Remote Worker: What I Learned Living in 3 Cities

Why I Left My Desk Behind

In early 2025, I made a decision that scared me more than I admitted at the time. I packed my life into a single suitcase, sublet my apartment, and started rotating through three cities over the course of nine months: Lisbon, Medellín, and Chiang Mai. I was a remote worker with a stable job, a decent internet connection, and a restless feeling that I couldn't shake. I had spent four years working from the same apartment, the same coffee shop, the same park bench — and while remote work had given me flexibility, it had also given me a kind of comfortable stagnation that I mistook for contentment.

The popular narrative about digital nomadism is glossy and aspirational. Instagram feeds show laptops on beachside tables, cocktails at sunset coworking spaces, and endless adventure against exotic backdrops. Nobody posts about the loneliness of eating dinner alone in a foreign city for the third week in a row. Nobody talks about the logistical exhaustion of finding reliable wifi, navigating foreign banking systems, or building a social life from zero every few months. I went in with moderate expectations and still found myself unprepared for the emotional reality of life on the move.

The Loneliness Nobody Warns You About

Lisbon was the hardest. I arrived in February, during the greyest part of winter, and the city's famous sunshine was nowhere to be found. I had joined a coworking space, attended networking events, and forced myself to say yes to every social invitation. But meaningful connection doesn't scale the way productivity does. You can optimize your workflow, but you cannot optimize friendship. True connection requires shared context, repeated exposure, and vulnerability — all of which are difficult to cultivate when you know you'll be leaving in three months.

I spent many evenings walking the steep streets of Alfama alone, listening to fado music drifting from basement restaurants, feeling the ache of the songs in a way that felt strangely appropriate. I learned that loneliness is not a problem to be solved but a condition to be accepted. Instead of fighting it, I started leaning into it. I took myself on dates — real ones, with good food and no phone. I wrote more. I read more. I discovered that being alone in a beautiful city is not the same as being lonely at home. There is a richness to solitude when it is chosen, even when it doesn't always feel that way in the moment.

The Daily Grind of Remote Work on the Road

Medellín taught me about discipline. The city is seductive — eternal spring weather, a vibrant nightlife, mountains that seem to rise straight out of the neighborhoods. It would have been easy to treat every day like a vacation. But I had a job to do, deadlines to meet, and colleagues in different time zones who depended on me. The discipline of working while traveling is not about time management. It's about identity management. You have to decide, every single day, whether you are a tourist who occasionally works or a worker who happens to be in a tourist destination.

I found that having a dedicated workspace was non-negotiable. Coworking memberships, noise-canceling headphones, and a strict morning routine were what separated productive weeks from wasted ones. I also learned that the digital nomad lifestyle is not cheaper than living at home — at least not in any sustainable way. Between coworking fees, short-term rentals, eating out constantly, and the occasional emergency expense, I was spending more than I had budgeted. The romantic idea that you can live like a king in Southeast Asia for pennies is largely a myth if you want reliable internet, decent accommodation, and a reasonable standard of living.

The Unexpected Gift of Impermanence

Chiang Mai was where everything clicked. By my third city, I had stopped trying to replicate the life I had left behind. I stopped looking for a permanent coffee shop, a regular gym, a consistent routine. Instead, I embraced the transient nature of my existence. I made friends knowing we would part ways. I explored neighborhoods without the pressure of mastering them. I accepted that my time in each place was limited and that this limitation was not a flaw but a feature.

There is a freedom in impermanence that is hard to access in settled life. When you know you only have a few weeks left in a place, you stop saving experiences for later. You take the trip. You have the conversation. You try the strange food. The awareness of endings sharpens your appreciation of the present. I found myself more curious, more open, more willing to be uncomfortable than I had been in years. The discomfort of constant transition had cracked open something in me that comfort had kept sealed.

Redefining Home After the Journey

When I finally returned to my home country after nine months, I expected to feel relief. Instead, I felt unmoored. My apartment, which had seemed perfectly adequate before, now felt small in a way that had nothing to do with square footage. My routines felt arbitrary. My friendships, while intact, had shifted in my absence. I had changed, but the world I left behind had stayed the same. The process of reintegration was harder than the process of departure.

I have come to understand that home is not a place but a set of practices. It is the rhythm of your morning, the faces of the people who know your history, the small rituals that ground you regardless of geography. I lost those when I left, and I had to rebuild them when I returned. The gift of solo travel as a remote worker is not the Instagram photos or the passport stamps. It is the uncomfortable realization that you can live anywhere, which forces you to confront the harder question: where do you actually want to live, and why? Not everyone needs to travel to answer that question. But for me, leaving was the only way to truly understand what I was choosing to return to.