S1E6: One Woman Band with Jess Arms

Jess Arms talks about her adventurous and alternative lifestyle, and fills us in on what it takes to make a living playing music while backpacking the world.

Traveling solo can be a frightening prospect. Especially for women. On the road, however, we’ve met some incredible women who are blazing their own trail without fear. Here’s the story of one amazing lady who travels alone and pays her way by playing music around the world.

Everyone should be able to freely roam this planet without concern for their safety.

Unfortunately, the stark reality is that an added element of danger exists for female travelers. And while it’s certainly important to be aware and alert, wherever you are in the world, it’s of equal importance to not let the possibility of a negative outcome impede you from living a life that you love.

That’s why it’s so important to me to share the story of my friend Jessie Arms. Jess is one of the most fearless and adventure-loving humans I have ever had the pleasure of meeting, and she’s been traveling solo for much of the last decade. A seeker of all things epic, Jess is constantly on the search for the next hike, the next dive, or the next wave.

Growing up in the suburbs of Baltimore, Maryland, Jess always felt the call of an alternative lifestyle, particularly one rooted in nature. She pursued a degree in Parks and Recreation Management in Maryland and completed a Wilderness Emergency Medical Technician certification in Yosemite, California.

In her early 20s Jess did everything from leading youth treks in the mountains of Wyoming to working on sailboats in the Carribean. She even organized a bicycle ride for charity across the United States, more than once! And not just east to west, but north to south as well.

As she continued her adventures, it was the wonders of the ocean that truly enchanted her. The next decade would see Jess spend as much time below the sea as above it, as she pursued her scuba dive master certification and became a PADI-certified dive instructor, working for conservation-minded companies across the world.

Randall and I met Jess during the Covid-19 lockdown in Sri Lanka, where she had been supporting herself as a solo musician—it was actually the first time we had been around another American for nearly two months. While our shared nationality brought us close, it was our shared love for music that truly made us feel at home together.

I think most musicians (back in the US, at least) would agree that it’s hard to make a living playing music. During our conversation with Jess, she shared her experiences playing gigs around Sri Lanka, including how much money one can make performing, how much work it takes, what kind of gear is required, and more.

We recorded this episode of Switch the Flip on one of our many excursions together, this time at the top of a tea plantation nearly 7,000 meters high. Dive into this episode of Switch the Flip to hear why Jess Arms is a true one-woman band.

Speakers In this episode:

Jess Arms

Jess has done it all. She’s cycled across America (twice), worked as a dive instructor, played music and surfed around the world, and worked on sailboats in the Caribbean. Most impressive, perhaps, is that she has never had any social media.

Randall Head

Randall had a good run at the corporate life (Blizzard Entertainment), but a series of devastating personal losses made him realize that NOW is the only time to live. Through music, yoga, surfing, and travel, he’s since been able to craft a life that’s anything but ordinary

Siler Head

An impromptu trip to India in 2015 illuminated Siler’s path, lighting the way to Alaska, Hawaii, and Southeast Asia. As his personal practice deepened, Yoga revealed itself as the natural outlet for all of his creative energies and ignited a passion to share with the world.