Ava Sinclair on Working Remotely While Traveling

THE INTERVIEW

Talking Remote Work and Travel with Ava Sinclair

In this conversation, we sat down with Ava Sinclair to talk about the realities of working remotely while traveling full-time. She shared how she stays productive on the move, the biggest challenges of blending work and adventure, and her advice for anyone looking to break free from the traditional office setup.

We asked her about the common misconceptions of remote work, how she balances deadlines with exploration, and what it really takes to build a sustainable career from anywhere in the world. Here’s what she had to say. 🚀

What inspired you to start working remotely while traveling?

“I always loved traveling, but for a long time, I thought it was something I could only do in short bursts—on weekends, during vacations, or if I took a break from work entirely. Then I realized that technology had made it possible to work from anywhere, and I asked myself, ‘Why am I waiting?’ I started small, taking my work on the road for a few weeks, and soon I realized I was happier and more productive than ever. The flexibility to choose where I wake up each day has changed everything for me.”

What challenges did you face when transitioning to remote work while traveling?

“One of the biggest challenges was creating structure in a lifestyle that is constantly changing. When you are traveling, every day looks different, which can be exciting but also distracting. I had to develop habits that kept me productive no matter where I was—setting work hours, making sure I had reliable internet, and balancing work with adventure. Another challenge was managing expectations. Just because I work remotely does not mean I am available 24/7. Learning to set clear boundaries has made a huge difference. Work should fit into your life, not the other way around.”

TODAY’S WORKSPACE

Live from Coastal Sagres, Portugal

When we sat down for this interview, Ava had just parked near the cliffs of Sagres, a quiet surf town tucked into the southwestern coast of Portugal. With the Atlantic breeze coming in strong and her dog napping after an early morning beach walk, she found a sunny spot outside her van to settle in. Her laptop balanced on a folding table, coffee in hand, and the ocean just within earshot — it’s the kind of setup she used to dream about.

Now, it’s just a regular Tuesday.

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How do you stay productive while constantly moving?

“I rely on a few core strategies. First, I plan my work schedule around when I am most productive. I know that I do my best creative work in the mornings, so I schedule deep work time early in the day. Second, I batch tasks. Instead of jumping between work and travel constantly, I dedicate certain days to content creation and others to exploring. And third, I make sure my workspace—wherever it is—is comfortable and distraction-free. Sometimes that means finding a quiet café, other times it is just a good pair of noise-canceling headphones.”

What advice would you give to someone who wants to work remotely while traveling?

“Start small. You don’t have to quit your job and travel full-time overnight. Test it out—work remotely for a week from a new location and see what works and what doesn’t. Invest in good internet solutions and time management tools. Most importantly, be clear about your priorities. If you are constantly stressed about work, you won’t enjoy your travels, and if you are too focused on exploring, your work will suffer. Find a balance that works for you. Productivity isn’t about location. It’s about habits and mindset.”

TRAVEL STAPLES

Ava’s Favorite Finds for Life on the Road

▶ Favorite remote-friendly city: Lisbon

▶ Podcast on repeat: The Remote Work Tribe

▶ Current read: The Comfort Crisis by Michael Easter

▶ Must-have gear: Compact tripod + Lightroom mobile

BLOOPERS

When Milo Decided to Take Over
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About ten minutes into the interview, just as Ava was explaining how she builds routine into her travels, Milo suddenly started barking at a passing cyclist outside the window.

Ava quickly muted herself, then dropped a message in the chat: “Sorry — Milo’s on squirrel duty today.”

We paused for a minute while Milo settled down with a treat, then picked up right where we left off.

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