What’s it REALLY like to work while traveling?
And is it worth it?
Are you daydreaming about selling your furniture, packing belongings, and working from a tropical beach somewhere far away from gloomy winters and 9–5 in the office? You are not alone! When working 40 hours a week in the office, imagining myself working from anywhere I wanted used to be my favorite escape fantasy. Back then, in the pre-covid times, working while traveling was something most people knew just from Instagram, and as we all know, Instagram does not always sell the reality. So, you might be wondering: Would this dream possibly meet my expectations?
I’ve always loved traveling, I was used to living in different places and moving around, and I was fed up with the monotonous life and gloomy winters in Amsterdam. So, after quitting my office job in 2018, booking a one-way ticket to South East Asia felt like the right thing to do. But I still had more questions than answers when packing for my first eight-month adventure.
While I still don’t have ALL the answers, I have worked remotely from Thailand, Cambodia, Laos, Malaysia, Indonesia, Taiwan, South Korea, Mexico, Curaçao, Croatia, Azores, Czech Republic, and Slovakia for over four years. And because many of you keep asking me about my life, I’m happy to share my experiences honestly, hopefully giving you new insights. Let’s begin!
I’m really into Thailand. I love this beautiful, spiritual country full of lovely people who like to have fun, beautiful nature, and mouth-watering cuisine. So when my dream finally came true, and I unpacked my belongings and laptop in Chiang Mai, I was mind-blown. I’m doing this! But then I realized one thing: I didn’t feel like working. Instead, I feel excited to explore the city, taste all the delicious street food, relax, and enjoy the scenery. I felt pressured to enjoy myself while I was there, and work, the remainder of my “ordinary life” back home, felt like a distraction. I had to force myself to go back to my apartment and focus, but often, I did not feel like it.
The typical representation of the “digital nomad” lifestyle on social media are pictures of bare legs with laptops on them or people having a fabulous time on a Zoom call in a cool hipster cafe. It almost seems like work is just something you do on the side, during your breaks between sightseeing, swimming under a waterfall, and watching sunsets. But the truth is that if you want your business to survive, you need to make it a priority. I needed to keep doing my best work no matter where I was and how many temptations I was surrounded with. And I could certainly not achieve it by working from a beach bar.
And so, I had to balance my work and enjoying each destination. And it was a puzzle that took me months, if not years, to solve, and I still need to reassess from time to time and change wherever it does not serve me. It’s easy to say, “Nah, I will deal with it somehow!” and yes, it is possible for weeks or months. But once it becomes your new routine, you will seek a sustainable solution because this is your life now.
So how to enjoy each destination while still giving your best at work? While at the beginning of my work-travel adventures, I would move from one place to another almost every week, currently, with an increasing amount of clients, my demands on the quality of my work, and perhaps my age, I prefer to stay in one place for at least a month or two so that I can find my rhythm, places to grab lunch between my calls and of course, enough time to explore the area and local culture. As a result, I’m more relaxed and become a tiny part of the local community.
Another obvious challenge is the one with different time zones and one’s energy levels. My clients are primarily based in Europe, requiring me to work in the afternoons and evenings while in Asia. Back in Amsterdam, I tend to be an early bird and typically quite useless after 6 pm. Coaching my clients requires a lot of mental energy and focus, so I must stay within the bounds of myself during the day. For instance, exploring Angkor Wat until 4 pm and then jumping on several client calls is not an option for me. So no matter how desperately I want to explore everything each destination offers, I need to always be honest with myself about what I can handle and plan accordingly. Work comes first during my dedicated working days, and I schedule days to completely disconnect, chill out and do everything that makes life on the road worth it.
And, of course, my coaching business is about more than just executing calls with my clients. No matter where I am, I must also keep dealing with admin work, acquiring new clients, continuing my education, and getting adequate rest. So besides choosing suitable destinations and determining the length of my stay in each place, it’s also essential to find suitable accommodations. Although remote work has become the new normal, and more and more people combine their travels with work, it’s still a massive challenge to find a room genuinely suitable for remote work: A room with a desk of adequate size, a comfortable chair, stable internet, walls thicker than paper and no ongoing reconstruction of the building is almost impossible to find. I succeeded a few times, only to end up with neighbors throwing a party on the balcony or kids screaming in the swimming pool in front of my window. But if I find the perfect accommodation one day, I will stay there forever and stop traveling. Just kidding!
This experience also teaches me to let go of perfectionism and a specific set of expectations. Each day differs from how I envisioned it, and I’m slowly learning to let go. I’m getting used to the fact that sometimes there will be an electricity blackout five minutes before a call with a client, that I will get food poisoned at the least convenient time, or there will be a giant spider chased by a lizard on the wall of my room when I need to focus on work. But we don’t always get to choose the “right,” Instagram-worthy type of adventure. And we can influence what we can, and it is not productive to stress about what might happen. If it does, you can deal with the consequences. If it doesn’t, great! And nothing is as big of a disaster as we tend to make it. Of course, except for the giant spider :-)
Conclusion:
I’m not a fan of the “escapist” portrait of working on the road on social media because it does not represent reality. The only thing you will escape by working from a tropical island is bad weather. And even that is questionable; Just try to stay on a tiny Thai island in the hot season and stay productive!
Wherever you go, there you are: with all your qualities but also your limitations and constantly changing sets of practical challenges. And that’s something it’s great to be ready for before quitting your “ordinary life” and getting your camera ready to make those fab Instagram posts.
So far, I find working while traveling worthwhile. Balancing uncertainty with both work and enjoyment and letting go of many comforts of a “stable” lifestyle is definitely not for everyone. Before taking the plunge, it’s essential to be prepared for the limitations and trade-offs of this adventurous path.
