Please enjoy this blog post about how to work and travel from Jesse Gernigin. You may remember him from the posts How I Went From Graduating College and Living in My Childhood Home to Running a Lucrative Coaching Business and Fast Start Freelancer Secrets: Getting Your First Client. Today, he shares practical tips for successfully working while traveling. Enjoy!
One of the greatest benefits of freelancing is the freedom to work from anywhere.
You’ve probably seen images and blog posts of exotic locations: people working from hammocks, airport lounges, and European cafes. The idea of combining travel and work is enticing—and with the right approach, entirely achievable.
I love traveling, which is why I shifted from a career in entertainment to full-time online freelancing. Since then, I’ve worked from many memorable places around the world, including:
- Rome
- New York
- Florence
- Nashville
- Horseshoe Canyon Ranch
- San Francisco
- Chicago
- Louisville
Along the way I hit plenty of bumps—late nights, missed meetings, and clients who weren’t happy. Over time I learned how to avoid those mistakes: I stopped taking calls at 3 AM, stopped missing tours to finish projects, and stopped worrying constantly about late payments.
It truly is possible to travel the world and freelance successfully without repeating my early errors. If you’re ready to learn how to work from anywhere and spare yourself the headaches of getting started, read on.
The Three Biggest Mistakes I Made While Working and Traveling
When I first started freelancing abroad, I made a number of avoidable mistakes. To help you avoid the same pitfalls, here are the three biggest errors I made—and how I fixed them.
Mistake 1: Mixing Up Time Zones
Remote work connects you with clients across every time zone, which is fantastic but also tricky. Even if you normally schedule meetings in your home time zone, traveling can make you forget the time difference.
I once missed an important meeting while in Rome because I forgot my time zone had changed. Thankfully the client rescheduled, but it was an avoidable error.
When you schedule meetings while traveling, always double-check time conversions. Use a reliable world clock or converter to confirm meeting times before committing.
Mistake 2: Scheduling Work Too Close to Free Time
I’m naturally organized and task-focused, which helps at home but caused problems in Rome. I scheduled work immediately before tours and day trips, which made it hard to get into a productive rhythm. If I finally found focus, I had to stop right away for sightseeing. While on the tour I felt anxious about not working.
I solved this by doing focused work early in the morning when the hotel bar was quiet. By the time the day began, I had accomplished my tasks and could relax. If you’re not a morning person, consider working in the late afternoon between returning from activities and dinner—those hours are often ideal for focused work sessions.
Mistake 3: Taking on Too Much Work During a Trip
On my second day in Rome I accepted a $2,000 landing page project that I estimated would take two days. It was tempting to ingest a large project while traveling—after all, it covered a big portion of the trip’s cost—but it nearly ruined the experience.
Halfway through, I realized I wasn’t enjoying the trip. I stayed up late to finish the work and was exhausted the next day, although I managed to enjoy the rest of the vacation. To prevent this, I now follow a simple rule: I allow two hours of dedicated work per day while traveling—either early morning or before dinner.
If a client wants a rush deadline and you can’t meet it, be honest and professional. Here’s a message you can use and adapt:
“I appreciate the opportunity. This project interests me, and I feel my skills fit the impact you want. For the next [X] days my schedule is limited as I’m traveling, so I can complete the project by [new deadline]. That is slightly past your requested date, but not by much. If that timeline works for you, I’d love to proceed. If not, I completely understand. Best of luck.”
This message is effective because it is honest about your availability and framed positively, showing interest and gratitude while offering a concrete timeline. Being upfront reinforces trust and often keeps clients onboard.
Despite the missteps, everything worked out: I delivered the landing page in Rome, satisfied the client, and ultimately enjoyed the trip. This taught me a lot about balancing opportunity and presence while traveling.
Why Many Freelancers Worry About Working Abroad
When I spoke with other freelancers about working while traveling, they raised three common objections. Here’s why those concerns are largely misplaced.
1) Clients Won’t Hire You If You’re on the Road
This concern is rooted in outdated corporate assumptions about remote work. Clients care about results, not your physical location. If you deliver value, your whereabouts rarely matter.
2) Your Work Will Suffer Because You Can’t Focus
That’s not inherently true. Location doesn’t determine performance—systems do. With the right processes, access to online tools, and a quiet place to concentrate, you can produce excellent work anywhere. In one example, a landing page I built abroad outperformed the client’s prior page by 17%.
3) You Can’t Make Money While Traveling
Also false. Some freelancers worry that being in different time zones prevents them from booking high-quality clients. What matters is how you present your proposal and whether you demonstrate you understand and can solve the client’s problem. Thoughtful, targeted proposals with relevant samples and testimonials win work regardless of your time zone.
Freelance Strategies to Succeed While Traveling
Over time I developed practical strategies to freelance effectively on the road. Here are three of the most useful tactics I rely on.
1. Secure Reliable Wi‑Fi
Working long stretches requires solid internet. Hotels—notoriously—can have inconsistent Wi‑Fi, whether high-end or budget. I’ve found coffee shops and even fast-food chains to be more reliable for focused sessions. Test connections before committing to a long meeting or deliverable window.
2. Keep Offline Backups of Important Documents
Don’t rely entirely on a live internet connection. Back up critical files to offline-accessible formats so you can keep working if connectivity fails. I use desktop word processors and the offline features available through browser-integrated tools. The tool itself is less important than the habit of ensuring access without internet.
3. Arrive Ready to Work
Travel limits the time available for work, so make every work session count. The night before, prepare everything you’ll need the next day: open files, bookmarked resources, notes, and any necessary logins. When you sit down, you should be able to start immediately without hunting for messages or documents.
Final Thoughts on Working and Traveling
I love freelancing remotely. It took time to develop habits that make my work seamless while I travel, but it’s now an enjoyable way to live and earn. You can successfully freelance anywhere by setting clear boundaries, preparing in advance, limiting daily work time, and communicating honestly with clients.
Jesse Gernigin is an author and marketing consultant who replaced his income by working online. He shares strategies for getting more clients, raising rates, and building a freelance business through his Freelancer’s Insider List.
Are you interested in learning how to work and travel? Why or why not?