Balancing Work, Travel, and Success: Lessons from a Digital Entrepreneur

Technology has given leaders the freedom to run their businesses from anywhere in the world, whether you’re working from a beach in Bali or a city like Chicago. For some, it means living abroad year-round, while for others, it’s about incorporating flexibility into a more traditional structure. But while the lifestyle may seem glamorous, it comes with its own set of challenges. Leading a company while on the move—whether occasionally, part-time, or full-time—requires discipline, adaptability, and a strategy to ensure that business doesn’t slip while you’re embracing the excitement of a new location.

I’ve had the privilege of growing my business strategy and coaching company while traveling to some of the most beautiful and culturally rich places in the world. Based in New York City, I spend part of my time working remotely from locations like Egypt, where I visit each year, or cities across the U.S. and the world, from Miami to Saudi Arabia to the Caribbean. These experiences have not only expanded my horizons but have allowed me to build a global network and client base, understanding different markets in ways that would never be possible from a single location.

There’s a unique challenge to being an executive or founder while traveling. You need to communicate with your team and stay productive. Running a business while on the go means committing to a balancing act. Here are a few things I like to do to make the most of my time while traveling:

1. Build a Work Routine That You Stick to, No Matter What: Before I travel to a new location, I plan where I am staying. I only rent apartments or houses that have dedicated workspaces. I always ask the host to send me a picture of an internet speed test to make sure I can work interrupted. Upon arrival, I immediately set up my workspace. I have the same morning routine, no matter what. I plan my day and stay consistent so I can stay focused.  When in Europe or the Middle East, I work from the early afternoon until the evening, so I start my routine after lunch. But, no matter where I am, I do many of the same things to make sure I stay focused on what matters most.
2. Turn Your Surroundings into Inspiration: Every place you visit has a unique rhythm and energy that can fuel your creativity in unexpected ways. I like to take time to immerse myself in the culture—whether it’s observing the architecture, trying new foods, or learning about local customs. I have a schedule where I take client calls three weeks out of the month and I only work on Friday mornings. I always have adventure days where I am able to see local culture and get inspired. I visit a coworking space in almost every city, which allows me to learn about local businesses and observe business customs. I also always spend the morning in a coffee shop—to me, the best thing about the culture is the people, so I always try to make new friends.
3. Use Local Events to Expand Your Network: One advantage of working remotely is the opportunity to build on your existing network. Traveling to new places allows you to interact with entrepreneurs, business leaders, and potential clients you may have never otherwise connected with. When you plan your travels, go beyond the usual conferences and trade shows. Explore regional events that might seem unrelated to your field—they could lead you to innovative ideas, unexpected collaborations, or even future markets. What unexpected opportunity could a local startup pitch night in Cape Town or a community event in Tokyo present for your business?
4. Build Cultural Competence as a Competitive Advantage: As someone who travels frequently, I’ve come to realize that cultural competence is more than just understanding customs and norms—it’s a competitive advantage. Being able to adapt your communication style and approach based on cultural cues can help you build stronger relationships, whether with potential clients or collaborators. Take time to learn key phrases in the local language and research business etiquette for each place you visit. Small gestures like greeting someone in their native language or following local customs can go a long way in building rapport. For example, in the Middle East, it is important for Westerners to dress according to the culture as well as to observe religious traditions. For example, when I was working in Riyadh, Saudi Arabia, the weekend started on Friday, which is the holy day. By Sunday, people were back to work. It is important to know that to avoid looking silly when scheduling or suggesting meetings.

Being a digital entrepreneur isn’t just about hopping from one beautiful destination to the next; it’s about creating a life that allows you to balance personal fulfillment with professional growth. While it requires careful planning and the ability to adapt to new environments, the rewards far outweigh the challenges. So, where are you headed next?