Remote work looks dreamy until your WiFi fails and your call is at 3AM

Working while traveling taught me a lot about focus, structure, and what it takes to stay consistent when everything around you is changing.

People online make it look easy. Coffee in Paris. Spreadsheets by the beach. But if you’ve ever done it, you know it takes real discipline. You need structure, focus, and reliable internet. Everything else builds from there.

I learned that after joining a socially conscious startup as a founding engineer. The role was remote, the mission was meaningful, and the freedom to move around came with a responsibility to still perform. That balance taught me the difference between romanticizing remote work and actually sustaining it.

Here are five lessons that stuck with me after working and traveling.

1) Be home when onboarding

Starting a new role already demands your full attention. Adding travel on top of it makes it harder to find your rhythm. When I joined the last startup I worked at, I stayed home for the first few months to get comfortable with the team, the stack, and the pace. That stability gave me confidence before I took my work on the road.

I had the Tokyo Marathon on my calendar six months out and was planning to run it. Having that goal on the horizon gave me time to build momentum and earn the flexibility to travel. By the time the race came around, I understood the systems, trusted my workflow, and could focus even in new environments. The early groundwork made the later freedom possible.

2) Internet access isn’t guaranteed

Reliable Wi-Fi decides whether your day goes smoothly or not. I’ve landed in cities where cafés looked great online but the connection failed once I sat down. Hostels were often worse. Some days the Wi-Fi worked, other days it didn’t. You adapt quickly.

I started booking places that supported remote workers and checking reviews for upload speeds. I learned to stay near coworking spaces and to always have a backup plan. When I wanted to visit remote areas, I saved them for weekends. Consistent connection isn’t just convenient, it’s what makes remote work possible.

3) Keep weekdays for work

I used to think I could mix sightseeing and work in the same day. It never worked. I’d end up rushing through both. Eventually, I realized I got more out of both when I separated them. I handled the work first, saved adventures for the weekend, and stopped feeling like I was falling behind on either side.

Having that separation kept me productive during the week and fully present on my days off. It sounds simple, but it changed everything about how I balanced both worlds.

4) Time zones will test you

Working twelve hours ahead of your team is possible but tough. Your morning is their night, your night is their morning, and that rhythm wears on you fast. I learned to plan my schedule around it like a night shift and protect my rest.

Over time, I found it easier to work from regions closer to my team’s hours. South America was ideal. It kept me aligned without constant fatigue. Picking locations that work with your team’s schedule makes everything smoother. It’s not about the hours you work, it’s about how alert you are when it matters.

5) Routine keeps you grounded

This mattered most. Routine was the anchor. For me, it was running, lifting, and signing on at the same time each day. Without that, the days blurred together. I saw plenty of remote workers burn out not because of the work, but because of the lack of structure.

I started running to local gyms or landmarks before work. It gave me a sense of direction, literally and mentally. After that, I’d find a reliable Wi-Fi spot, lock in, and get things done. Structure made spontaneity easier to enjoy later. It’s what kept me steady no matter where I was.

Working while traveling isn’t permanent vacation. It’s a balance between exploration and consistency. The better you are at keeping your rhythm, the longer you can sustain it and actually enjoy it.

Bonus: Being intentional about where to stay during the work week

If I was ever tempted to stay somewhere like the Insane Monkey Party Hostel, I always checked that the Wi-Fi actually worked. More importantly, I avoided places like that during the workweek. Rest, focus, and space to think are essential when you’re working. The louder spots are best saved for the weekend.

After a stretch on the road, I always make it a point to go back home. I love being there. Travel has never been about escaping for me. It is a way to explore somewhere new when the cabin fever of remote work sets in. A short change of scenery gives me energy and perspective.