6 Lessons I’ve Learned Being Self-Employed and Traveling for 5 Years


Five years is a lot of anything, but five years of traveling as a digital nomad can be as exhausting as it is exhilarating.

I often joke that I am “homeless” because the past five years have been a big blur of rooms, apartments, and houses in over 70 cities in 30 countries. Apartments rented on Airbnb, a borrowed bed from a kind Couchsurfing host, a room in exchange for volunteer work with a Workaway host, even a house-sit on a small, remote farmhouse with 100 chickens.

For me, being on the road has never been about a vacation, it’s simply been my way of life. I travel and work, often at the same time. On the bus from Bulgaria to Istanbul or on the train from Bangkok to Chiang Mai.

Just like all of us, I have to support my lifestyle with a job, and my job as a freelance writer happens to be remote-work friendly. If a nomadic lifestyle is something you seek, at least for a little while, believe me, it can be done. It’s not easy to generate income as a digital nomad, but then again, nothing that’s worthwhile is easy, right?


Here are six of the most impactful life lessons I’ve learned so far, from my time as a self-employed digital nomad.

1. Self-Confidence Comes from Getting Lost.

It happens every time.

When I exit the airport, train station, or bus station, I am suddenly thrown into the chaos of strange smells and sounds, odd stares, and funny shop signs. Everything is so different and overwhelming, but I am ecstatic; I crave this challenge. It’s almost like being a little kid, but no one’s there to lead me by the hand.

After a few steps, I sort of get my bearings and start to ask people on the street for help (in English or whatever scraps of the local language I know). They smile (or not) and point me in the right direction. Most likely, I still get lost, I wander, but then I check my map (paper not GPS!) or ask someone else. And finally, I reach my destination.

Do this frequently for five years, and I guarantee you will be able to deal with whatever life throws at you.

It’s a damn good feeling, and this increasingly confident attitude also manifests itself in your work life, whether it’s marketing yourself, negotiating, making calls, or even through the way you create. Working remotely for even a short period of time, can teach you a great deal about the importance of building self-confidence in business.

2. If Nothing Else, Be Flexible.

I tell everyone, ‘Oh yes, I’m so lucky that my job is flexible,’ but really, that’s only because I’ve made it so.


I’ve made many careful decisions over the years, to design a job that allows me to be very flexible, and carry my work with me wherever I go. I worked hard to build up a particular roster of clients who do not micromanage or demand constant attention via email and Skype. They don’t care if I am based outside the U.S., and they mostly pay me via PayPal. I arranged my working hours to fit various time zones, mostly in the U.S.

In certain countries, I’ve had to seek out weird places to access wifi. One time in a village near Granada, Spain, I Skype called with a client from my laptop in a tiny park across the street from a loud bar that had free wifi, all because my apartment had no internet. I sometimes have to conduct work calls very early or very late in the day, due to major time zone differences.

Flexibility is a basic necessity for the traveler who constantly weaves in and out of different cultures, and comfort zone. The working traveler needs to be twice as flexible to thrive abroad.

3. Going Offline is the Goal.

I lived for several months at a time in a couple remote villages that had little to no internet access.

I never had a smartphone (sometimes I had no phone at all), and some of the places I traveled to were mostly unaware of the concept of smartphones. My travels taught me to live without the constant need for internet access. I weaned myself from this addiction. This, for me, is critical to having a healthy work-life balance, especially as a digital nomad.

Traveling while I worked, helped me to realize that you can survive for days, even weeks without email, Facebook, and watching TV shows online.

Being offline (when I didn’t have deadlines) gave me more time for reflection, to think deeply about my work ideas and personal projects (and actually pursue them), to be bored and enjoy that boredom, to meet people and have real face-to-face conversations, to go hiking in the mountains for days, to remember how slow life used to be and still is for many parts of the world, and how slow is not a bad thing.


I realize, of course, that without internet access around the world, I could never have this digital nomad lifestyle that I love.

But from the offline time that I treat myself to, I learn how to more efficiently make use of my online time for work, travel research, and finding people & events in a new city. Knowing when and how to step away from the screen and dive right into the world outside is the entire point of working and traveling at the same time.

4. Let Your Environment Inspire You.

If it doesn’t, do something about it. Because you can. If my apartment or a cafe doesn’t feel right for working, I’ll leave and find another spot, or take a break to walk around and clear my head. On a larger scale, if the atmosphere of a city doesn’t feel right for me, I know I can move rather quickly, thanks to monthly rentals on Airbnb.

The constant movement and change I encounter as a digital nomad has opened my eyes to the fact that everything is transient. No place is perfect, no situation in life is perfect. You’ve got to either make the best of your situation, or move on and create something better.

5. Take Time to Connect with Others.

I don’t usually travel to a city because it’s a hotspot for digital nomads. But this year, I finally had to see what the Chiang Mai hype was all about.


I’d been to Thailand before, but only spent time in Bangkok and a nearby beach town. So last year, as my travels took me further east through Tbilisi and then Dubai, I began to research the digital nomad hotspot of Chiang Mai for tickets and apartments. I ended up spending a month in Chiang Mai, a beautiful, peaceful, green and temple-filled city.

I met quite a few digital nomads from all around the world (Facebook groups are very helpful with this) for fun and networking. By time I left Thailand, I had a great new client who has his own very wide network that can potentially bring me more work over time.

Although I’ve previously found new clients by networking when I lived in one place for a year or two, this type of quick connection had never happened for me before. It helped me realize the power of meeting new people face-to-face and making connections on the road.

6. Work Comes in Waves, and That’s a Good Thing.

Something else that I came to understand as a traveling writer is the transient nature of my work.

Just as I move from country to country, have wonderful and difficult experiences, meet new people only to say good-bye, my work as a freelancer also ebbs and flows. I chose to be a digital nomad, which means I chose an unstable line of work, by definition. Even when I lived in one place for a longer period of time, I still didn’t experience much stability in work.

The winter holiday season, for example, is very slow most years, and although I first freaked out about this lack of work during these couple months, I came to see a pattern and prepared for this time accordingly. I always had enough money saved, but I also tried to pick up extra work right before this slow period.

I also realized that this was exactly what I wanted to happen. This was how I could increase my work-life balance. Because I didn’t have many deadlines and most clients (including potential clients) would not be responding to emails over the holidays, I took advantage of the downtime to work on my personal projects, head out on faster-paced travel adventures, or get completely off-grid.

And almost magically, when I slowed down again and was ready for more work, it always came.

Whether you travel for a quick weekend getaway, or take on the digital nomad lifestyle, travel is the physical manifestation of stepping away to look at the big picture. When you can see yourself and the world from a new perspective, you will come to understand your life’s passions and goals more clearly.

Whether you’re just starting a freelance career, or looking to grow your existing business, download our free eBook, The Freelancer’s Roadmap.



Suchi Rudra

Suchi Rudra is a nomadic writer of articles, stories and songs, taking inspiration from her travels. Follow her wanderings at Tread Lightly, Travel Naturally.