These Three Digital Nomad Planners Travel the World While They Work
They're living their dreams while running their businesses, managing meetings, and staying involved with the industry — but it isn't always easy.
Ashley Lawson: A New Life as a Global Local
Ashley Lawson made a big decision in December of 2020. She wanted to set an example of how to travel safely during Covid, and share what different destinations, like Mexico, were doing to welcome guests back. So she and her husband “packed a backpack with all of the digital things that we thought we would need to work remotely from around the world. And we set off.”
She has been working from the road ever since: Kenya, the Dominican Republic, Colombia, Guatemala. A “full-time traveling event prof,” as she calls herself, she runs her third-generation business, Achieve Incentives & Meetings, manages events, stays involved with the industry, and posts regularly on Instagram about her adventures (@ashleyroseontheroad) — all from a suitcase.
Lawson and others like her have taken what most people would dream of and made it their reality. Today, 11% of U.S. workers call themselves digital nomads, growing more than 147% since 2019. The couple stays entirely at Airbnbs. “We live for a while off the beaten path, but then I make it to a city that could work for an incentive and I use it as a learning opportunity and do as many site visits as I can.
“I become a local in every destination I visit. It’s almost like I’m doing a needs assessment, and learning about the people and their history. I think it’s so important that we introduce our event attendees to the culture.”
Agnès Canonica: Changed Jobs to Pursue the RV Lifestyle
Like Lawson, Covid was the turning point for Agnès Canonica, event marketing manager at Amplity. Over her 30-year career, she had spent half her time traveling for work. During the shutdown, she and her husband discovered RV life while watching a TV series, and purchased a Class C Thor Freedom Elite in October of 2020. They equipped the RV with all the essentials for boondocking and opted for E-bikes instead of towing a car. She loved the freedom she felt taking trips to explore the East Coast while working remotely.
In 2023, she decided to change her life for good. “Severe burnout led me to reassess my path. I transitioned to a new role that prioritized flexibility and reduced my travel to less than 10%. It took months of searching to find the perfect position, which lets me work remotely while taking RV trips.” Next up is a three-month West Coast trip in 2026.
Meredith Wolff: Started Her Own Business and Traveled the World
Another digital nomad, Meredith Wolff left her role as director, global events and sponsorships at PGIM in 2023. Her plan was to take a year-long sabbatical pursuing her lifelong dream of seeing the world, then start her own company, EventRx.
She has traveled to more than 30 countries spanning five continents, and, like Lawson, sees her solo travel as an asset to her clients. She says that, although worth it, the lifestyle comes with challenges. Among those is finding the balance between working and experiencing new environments.
“If you’re traveling through Asia, for example, and you work on Eastern Time, you’re prioritizing work, and you also want to experience your new surroundings.”
The constant planning and booking of travel and managing visa and entry requirements take up time, as does making sure she has the necessities she needs, from toothpaste to clothes. “You have to shift your expectations as far as certainty and routine, and embrace adaptability,” Wolff said.
“So your home becomes your bag, in a way. But I love that, because I’m interested in being minimalistic.”
“It’s almost a full-time job in itself living outside of the United States,” said Lawson. “My husband and I have a weekly planning meeting around what needs to happen, from car rentals, to housing, to flights, to visas, to currency exchange, to downloading languages and Google Translate.”
Time zones can also be a big issue. Lawson and her husband decided to work on Eastern Time, which is the time zone for her team in Cleveland, no matter where they are in the world.
For Wolff, the biggest challenge has been maintaining relationships from a distance. “You have to actively work at it because you’re not there. So I watch my group chats and I make the effort to stay in touch with people. But you also want to be present in the place where you are, so it’s a balance.”
Canonica has found RVing to be the perfect solution for balancing life, work and family (which now includes grandchildren). All she needs is reliable internet, a bag packed with her professional outfits, and an airport nearby. “I’m very grateful for the opportunities it provides to live life to the fullest — working under an awning, enjoying changing landscapes, and finding joy in every moment.”
Lawson, who just turned 40 and had her first baby, is getting ready to head to Argentina. “There’s no plan to stop, but it’s definitely slowing down,” she said.
This article was originally published by Skift and has been republished with permission.
