January 28, 2025, 6:54 am | Read time: 11 minutes
TRAVELBOOK author Anna Wengel (now Chiodo) loves to travel the world. She often earns her money on the road, writing and coaching. How does that work? She revealed it to TRAVELBOOK.
A blind dog bumps into a Buddhist monk and then moves past him. The man smiles and continues on his way. Just around the corner, a little boy appears at that moment. He smiles at me and runs straight towards me. Comes very close. Looks over my typing hands at the laptop. Trying to read what it says. “What are you doing?” he asks me in surprisingly good English, leaning in to peer at the white document on my laptop filled with snippets of text for a travel report I’m currently working on. “I’m working,” I reply with a grin. “And what about you?” “I’m working too,” he says.
To prove his point, he holds up the coat hanger in his hand. Numerous knotted bracelets hang from it. “What do you do?”—and there, in this street café in Cambodia’s capital, Phnom Penh, I find myself in the middle of another how-can-you-travel-and-work conversation. I find myself in that conversation quite often. Because it might become more and more normal to type away on a laptop somewhere in the world and to then send the result to someone else somewhere else in the world. Yet, many people still wonder about the specifics of how this lifestyle actually works. Including the little boy, who is primarily interested in two questions: “How much do you earn?” and “How does that work?”
How Do You Work and Travel? One Model
For me personally, it works like this: I work as a freelance travel journalist, author, and coach, often while I’m traveling. In practical terms, this involves jetting off to various countries with my laptop and writing tools in tow, always in search of a stable internet connection and a tranquil spot to work. Why do I do this? Quite simply: because I love it. I’m living the life that I want to live and that I used to dream of. Even if it’s different than I first thought.
That’s how I got here:
In my early 20s, I wanted to be a war reporter. With this dream in mind and driven by my university thesis on Afghanistan, which quickly turned into a thirst for adventure and a desire to see for myself, I flew to Kabul with an NGO. Kabul in 2012 awaited me and I experienced inquisitive young children, women under burkas thinking of progress, men with machine guns and wit, high walls with barbed wire, military helicopters, and explosions. Confronted with real threats and feelings of fear that completely overwhelmed me, I finally changed my mind about being a war reporter.
Initially, it felt like a setback. It took some time for me to come to terms with the fact that I didn’t want to be a tough war reporter. Eventually, I realized that dream tests and perceived setbacks are part of the process, so I didn’t give up and could simply reformulate my dream. Because I wanted to continue writing and traveling. But not necessarily to war zones—at least for the time being.
I stayed in Berlin for a few more years, completed my Editor traineeship, and, after that, became a freelance journalist and traveled a bit. Until the next concrete dream became clear: Portugal. I wanted to live there more than anything else. So I needed jobs that I could take with me. Writing was still firmly anchored in my life plan. It took a while, but then I had two clients who agreed to me working on the road: an online magazine that allowed me to work in shifts and an agency that sent me topics to write about as needed. This arrangement resulted in a steady income, with one larger and one smaller sum coming in each month. Enough to live locally, drive a car, feed myself, and even put a bit aside.
Living and Working in Portugal
So I flew off and lived my dream. And it was a dream. For many reasons—one of them being my mobile office: I bought a very old, very rickety Polo that I loved madly. It reliably carried me to my favorite cliff near Monte Clérigo beach in the Portuguese Algarve, though sometimes it was a bit temperamental. There I sat sideways in the driver’s seat, leaning against my driver’s door, my legs on the passenger seat. All the windows open—after all, I wanted to hear the waves—and I wrote. Wrote, wrote, wrote. For hours on end. With a view of huge waves, the blue ocean, and the horizon. Until, at some point, my back hurt. Or the laptop battery ran out. Or that of my mobile WLAN router.
On other days, I worked on the terrace of my apartment, gazing at the pretty white-built Aljezur below me and the brown-green Monchique mountains beyond.
Then there was this phone call: the magazine (the bigger chunk) no longer existed. Gone. Finito. Everyone fired. At first, I couldn’t grasp what had happened. I stood there, feeling as if I’d been slapped in the face through the phone. Alone and without my supposed financial safety net. Shock, panic, and gasping dream-burst scenarios followed. I didn’t want to go back to Berlin (in my head—fortunately only for a moment—there was only this solution).
After the initial shock, I reacted with crisis management actionism: I reached out to numerous magazines, agencies, and former colleagues. And then I waited. And I agonized over my worries. Had my dream of travel and work been shattered? My financial buffer was dwindling. What would happen once the money was gone? The small chunk only covered part of the necessary expenses. I needed a job. Any job. A few days later, I started cleaning a guest house for a bit of money. With that and the small amount, I was able to make ends meet and relax.
Then the offers came. Suddenly, several magazines and agencies allowed me to send articles that didn’t have to be written in their editorial offices. At one point, I had six clients at the same time. That felt like freedom. At the same time, I immediately realized that everything could change at any time—and I learned to live with this uncertainty more and more.
Work and Travel: From Portugal Out Into the World
Then my dream changed again. At the end of my first year in Portugal, I flew to India and Sri Lanka for several months—and realized back in Portugal that I wasn’t quite as happy here as before. Something was missing. I was restless, I wanted something else. Today I think I was bored. Aljezur and its surroundings were still beautiful, still my idyll. But always the same. I wanted to see more. Do more. Experience more. And I wanted much more freedom. So at the end of my second year in Portugal, I made a new decision: I gave up my apartment and my car. And flew off.
With a one-way ticket to Vietnam, on to Cambodia, on to New Zealand. I had the quasi-security of several clients with me, for whom I was allowed to write more or less along the way. In New Zealand, I bought myself a new home: an old van (read more about my New Zealand van life here). There it was—the freedom I had longed for.
I went wherever I pleased, did whatever I fancied, and all on my own schedule. Climbed mountains, swam in rivers, lakes, and the sea, swung on the highest swing in the world, and almost froze my butt off when the temperatures dropped to below zero out of nowhere and it started to snow. And loved it, loved it, loved it. From New Zealand, I flew on to Australia. After a short break in Germany, back to Portugal, Thailand, South Africa, and Portugal again. And I loved it.
I loved it to travel through New Zealand in the van and stopping in between to work, sitting in the open tailgate while the landscapes changed outside. Sea, mountains, lakes, fjords, green meadows, gray parking lots. I loved sitting in that very street café and observing the normal everyday life in Phnom Penh while I sat quietly in the middle of it and wrote about exactly what was happening in front of me. I loved sitting on a terrace on Koh Phangan writing, watching the masses of water rushing out of the clouds above me and turning the meadow in front of me into a muddy landscape. I loved sitting in hipster cafés in Ho Chi Minh City and Byron Bay and seeing what the fashion trends of the day after tomorrow would look like. I loved it. So much.
And yet, after some time, a yearning began to grow within me. First, just a little, then a little more, and finally, much more than just a little.
I Longed for a Real Home
For a place I could come back to, that was mine. I had parents and friends I could go to and stay with whenever I wanted (and if any of you are reading this, thank you so much!). Yet, I yearned for a home that was truly my own. An apartment with my books and my bedding. A place that is not temporary and where I can just be for as long as I want. I also longed for my friends and family. People I’ve known for more than just a week, some of whom have been with me my whole life.
Parallel to these longings, a new dream developed along the way: Coaching. It was the missing piece of the puzzle that I finally identified in New Zealand, an idea that had been lingering undefined in my mind for half my life. Until I was able to name it. That’s how I finally came back to Berlin. My coaching school of choice is actually based in the US. It offered a training in Berlin at the perfect time for me.
Experience report You Want To Earn Money While Traveling? Here Are 11 Tips To Realize Your Dream
With job examples 5 Types of Work That Make Long-Term Travel Possible
TRAVELBOOK author reports Why Wintering in Portugal Isn’t All Good News
Berlin, Portugal, and Parenthood
And there I was again. Back in Berlin. Planned for six months, I stayed for three years thanks to a new relationship and the coronavirus pandemic. Interrupted by shorter and longer stays in the US, Portugal, and Australia. Eventually, I (and fortunately also my partner) were seized by a longing for Portugal again.
Now married and parents, we finally packed our minivan full of things and set off on a new life in Portugal. This time as a trio and near Coimbra. It felt very different to being alone and right by the sea. With a child, my needs changed. My love for Portugal was the same, but my longing for family and long-time friends continued to grow. Eventually we packed our bags again, not without promising each other that we would create a second home in the south of Portugal in the near future, and after nine months we returned to Germany.
Now I have my home of longing, where all my books live alongside my husband and daughter. And that’s also why I have the mental space to plan big trips and think carefully about how the concept of two places of residence can work. I continue to write and coach people, sometimes both together. For me, work and travel still go hand in hand, but with a home in mind that we can and want to return to again and again. Have I reached the end of my dream? Certainly not. I’m continuously shaping it. Just like me, my dream life continues to develop.
The little boy in Cambodia gave me a life tip back then: “Don’t work too hard. There’s always tomorrow,” he advised. I often think back to that. Like when my plate is overflowing with tasks. Because now, striking a good balance between screen time and time unplugged is clearly woven into the fabric of my life.
In the second part of this series, I have written down how this can work, as well as many other tips that can help make your dream of traveling and working on the road a reality: Part 2: You Want To Earn Money While Traveling? Here Are 11 Tips To Realize Your Dream). And in the third part (Part 3: 5 Types of Work That Make Long-Term Travel Possible), you will learn about a few jobs that are well-suited to traveling, and I will give you tips on how to turn almost any job into a travel job.