Despite high-flying careers, entrepreneurs enjoy a travel side hustle

As the travel industry rebounds, we’re all looking forward to brighter days ahead, especially these entrepreneurs who have built blossoming sideline careers in the travel industry.

Doctor on the case

Since March 2020, Dr. Calvin D. Sun, a physician and clinical assistant professor specializing in emergency medicine, has worked on a per diem basis at the majority of the health-care systems based in NYC, especially during the COVID-19 pandemic. But even though he’s saving lives by day, he’s offering help for wanderlusting souls by — well, whenever he has a day off from the emergency room.

As the founder and CEO of the Monsoon Diaries, a tour company that runs adventure-focused trips around the world, he has visited 190 countries in the past 10 years and taken more than 1,000 travelers along for the ride.

“It began as a simple travel blog for a particular May 2010 trip to Southeast Asia and India the summer I was to begin medical school — much like the premise of [Ernesto ‘Che’ Guevara’s book] ‘The Motorcycle Diaries’ — and during the monsoon season no less, hence the name,” he said. “I had no idea at the time it would go anywhere farther than just that, expecting instead to cease posting the day I returned and begin medical school.”

However, Sun, now 34, felt burned out after a month into medical school.

Dr. Calvin D. Sun felt burned out after a month into medical school.

“With the fortuitous arrival of a wedding in San Diego, I left. I returned [re-energized] with the curious thought that spontaneous weekend trips may actually be the answer,” said Sun.

A month later, he embarked on a 48-hour jaunt to Hong Kong and blogged about that experience, too. Micro-trips — or what Sun calls “monsoons” — followed, to North Korea, Guatemala and Belize for Thanksgiving weekend, and Iran for a winter break, all chronicled on his blog. A grassroots business blossomed, and before long, Sun was running trips across the globe.

When the pandemic hit, the nimble doc was quick to shift the focus of his blog.

“I immediately began reporting on COVID-19 and what I was witnessing on the front line in the ERs around NYC,” he said. “I’d apply the same genuine approach of blogging about my work and what I was experiencing at home. Given my years of always writing in the moment while traveling, the transition was seamless.”

In fact, the Monsoon Diaries’ online presence actually grew during the pandemic. Today, his travel business is booming.

“After four months of being fully vaccinated and over 15 months of staying grounded on the front line of the pandemic, I set out in May 2021 on a solo research trip, and then, beginning in June 2021, have consistently led group monsoons every month since,” he said, adding that his company has been more active than at any point in their history.
His advice to aspiring travel-preneurs?

“I cannot stress this enough: Don’t do it for the money, and genuinely commit to that concept. If you stay authentic without expectations, the right people will find you,” he said.

Sun is also all about embracing your inner Forrest Gump, jogging around the country, “because you ‘just felt like running,’ ” he said. “Maybe that’s a sign you’re jogging in the right direction.”

Rebecca Garland knew her love for getting out in the world would morph into something more.
Barb Thrall

Lawyering up and away

With a full-time job as the discovery attorney at a midsize firm in Seattle, Rebecca Garland, 46, certainly logs a busy 9-to-5. Still, when the solo travel bug bit in 2009, she knew her love for getting out in the world would morph into something more.

“In 2011, I began attending women’s fitness retreats around the world. I realized that not only did those experiences allow me to connect with other women who had a passion for travel, it also allowed me to return to my career as an attorney feeling more relaxed and refreshed,” Garland said. “During a retreat I attended in Mexico, I was sitting on the beach one day when it occurred to me that I could start a company offering retreats for women that weren’t tied to a specific location.”

In 2014, Garland and her business partner founded Fit & Fly retreats. Since then, they’ve hosted hundreds of women on retreats on five continents, ranging from Iceland and the French Riviera to Costa Rica and Mykonos.

travel industry side hustle
Rebecca Garland and her business partner founded Fit & Fly retreats.
Bree McCool

So how does she make the seemingly disparate careers work? Outsourcing is the answer, friends.

“I’m able to juggle Fit & Fly along with my full-time legal career as I have found wonderful hosts, fitness instructors, chefs and many other people to help care for our guests during retreats,” she said. “I now attend one Fit & Fly retreat a year, and just like when I was attending retreats before founding the company, I absolutely love the connections I make with our guests during the week.”

After putting things on pause during the pandemic, they’ve been able to launch a full slate of retreats for 2022, with most of the events already sold out.

travel industry side hustle.
Fit & Fly has been able to launch a full slate of retreats for 2022.
Bree McCool

For anyone interested in starting a side hustle in travel, Garland’s first advice is to “get out there and really learn the industry by traveling,” she said. “I also recommend connecting with travel experts and learning from them. Find your niche, whether that’s a specific location or a specific type of travel. Finally, figure out if your full-time career can support flexibility, whether in your hours or where you can work. If you have the capability to work remotely, that will help with any traveling you need to do for your side hustle.”

Garland’s also a firm believer in the concept of leaping and trusting a net will appear.
“When I co-founded Fit & Fly, I’d never started a business, but I didn’t allow that fear of the unknown to hold me back,” she said. “I had an idea I loved and a passion for travel, so I jumped in head first.”