The pros & cons of working remotely while traveling
Years of working on the road can inspire anyone to start their own company. The freedom to work wherever, whenever, is often the driving factor. From living in Berlin to calling Beirut home — a city with daily rolling blackouts — the remote lifestyle is all about chasing unique experiences, like catching the excitement of Formula 1 in Doha while still meeting every deadline.
The takeaway? Remote work might look glamorous, but it requires experience, flexibility, and a high tolerance for unreliable WiFi. It teaches adaptation, focus, and balance. It’s easy to get distracted by surroundings, but success comes down to discipline and a strong work ethic.
The freedom is real, but so are the challenges
Preparing for a month of travel while working the entire time is a common scenario for remote entrepreneurs. When you’re the boss, there’s no out-of-office — client deadlines and deliverables still need to be met. Running your own business, whether it’s an agency, consulting practice, or freelance gig, means the freedom to travel comes with responsibility, planning, and trade-offs.
Key challenges and how to prepare
To make your trip successful, you need to plan ahead. Here are some of the biggest challenges to prepare for:
Time zones
Time zones can make or break a schedule. Late nights or early mornings might be necessary to stay aligned with clients or a team. Keep your computer set to the home time zone to avoid confusion, and let your phone update to the local time for navigation. Don’t forget about daylight savings time — some countries don’t observe it, which can complicate things.
Reliable WiFi isn’t guaranteed
Always vet accommodations for strong internet. Have a backup plan, like a mobile hotspot or reliable data plan. Relocating on the fly due to bad WiFi can happen. Estimate data needs based on work — video editing or large file transfers require more bandwidth. Check with phone carriers for long-term international plans, as daily add-ons can quickly add up.
If flying, research airport lounges and WiFi access tied to the ticket, airline status, or credit card perks like Priority Pass.
Finding workable spaces
Identify reliable workspaces ahead of time, like cafes with WiFi and outlets. Choose accommodations with a desk, balcony, or extra room if separation is needed. For longer stays, consider co-working spaces — they’re great for productivity and networking, especially those with programs or events. Services like Noma Collective can handle these details for you.
Set boundaries
Being away doesn’t mean being always available, but it also doesn’t mean being on call 24/7. Communicate clear working hours with clients and colleagues. Update tools like Calendly to reflect the current time zone. If clients follow on social media, be transparent about the work schedule and travel arrangements.
This is still work, not a vacation
The lifestyle is rewarding, but it’s still work. Deadlines, deliverables, and daily responsibilities don’t disappear just because of a new location. Plan activities around working hours to maintain productivity and enjoyment.
Entrepreneurship requires risk, but it’s worth it
Running a business has its ups and downs, but the freedom to live and work on your own terms is worth it. There’s no need to ask for PTO or stick to a rigid schedule.
Remote work isn’t always as idyllic as it looks online, but for many, the challenges are worth it. It’s about creating a life and a career outside the traditional 9-to-5 — a model that doesn’t fit everyone.
Final thoughts
Pursuing an unconventional career path or lifestyle comes with its own set of challenges, but the rewards can be extraordinary. The ability to design a life that aligns with your goals and values offers a level of fulfillment that’s hard to match.
Whether it’s entrepreneurship, remote work, or stepping away from traditional structures, taking the leap requires courage and adaptability. However, for those willing to take the risk, it can lead to a sense of freedom and purpose that makes the effort undeniably worthwhile.