Jill Thomas is a Canadian and American Rambler, traveler, and storyteller with a big laugh who believes life takes her where she needs to go, no matter the roundabout path.
Where did you grow up, and where do you live now?
I was born in Calgary, Alberta, Canada, but my family soon moved to Edmonton, where I started school.
When my parents separated during Grade 2, my mom moved us to Port Moody, British Columbia. I remember being wildly excited to see the ocean for the first time — and oddly worried that everyone else would collect all the best seashells before I got there.
Port Moody is a bustling city today, but back then it was a small town, and by high school I was dreaming of something bigger. At 17, I moved to Toronto to live with my dad, and experiencing big-city life for the first time felt thrilling and full of possibility.
I finished high school in Toronto, where I met three of my fellow SSR founders — Jill Cohen Morris, Tara Romoff, and Naomi Weisman. I still adore Toronto and return whenever I can.
In my twenties, I moved frequently between Victoria, Vancouver, and Toronto before eventually settling on Salt Spring Island in British Columbia. There I met my husband, ran a couple of restaurants, and raised our family on what we fondly call the Salty Isle.
After our children graduated, I accepted a job in Pensacola, Florida, where we lived for nearly 13 years. Life there was wonderful — we called one of the world’s most beautiful beaches home and built a tight-knit circle of friends. We also made many trips to New Orleans, a city I love more than almost anywhere else.
In April 2024, we returned to Canada and to our beloved home on Salt Spring Island, closing one chapter and beginning another.
What do you most like to do in your spare time?
I used to jog regularly, and although I enjoyed walking, it wasn’t something I did consistently — and never on my own.
Near the end of the pandemic, I visited my longtime friend and fellow Sole Sister Ramblers founder, Jane Witherspoon, at her home in Panama. Jane is an avid hiker and took me on several challenging trails which quickly made me realize I was not nearly as fit as I thought I was.
Determined to change that, we signed up for a virtual Camino walking challenge together — 420 miles in two months. And something unexpected happened - I fell in love with walking.
I gave up jogging, and a long daily Ramble became part of my life. The more I walked, the stronger I felt — physically and emotionally. In the years since, I’ve grown fitter than I’ve ever been and discovered just how powerful simple, steady movement can be.
Rambling is now something I genuinely look forward to every single day. It supports my physical health, clears my mind, lifts my mood, and connects me to the world around me. I’ve become a proud Rambling evangelist and love sharing this life-changing passion with the Sole Sister community.
What is your favorite music, and what influenced your musical taste?
Living in the southern United States for 13 years — just outside New Orleans — changed my musical tastes forever. I fell in love with Americana, a rich blend of American roots styles like folk, country, bluegrass, blues, and roots-rock.
My husband affectionately refers to it as Jill’s “plonkety-plonk” music
What invention in your lifetime are you most amazed by?
The Internet! In 2007, a friend introduced me to what was then called Web 2.0, and my mind was blown. Suddenly, I realized I could share my thoughts and promote my business online — no coding required. It felt like a true turning point in my life.
I was instantly hooked and started a blog called Island Chef, which made perfect sense since I owned a restaurant at the time. About a year later, we sold the restaurant, and I teamed up with three friends to launch a digital marketing agency. It didn’t succeed, but it completely changed the trajectory of my life and eventually led me to Florida — a move I’ve never regretted.
These days, I still spend many hours (perhaps too many!) with a laptop on my lap, happily tapping away and sending words, stories, and photos out into the world.
What are the top 5 things on your bucket list?
I am obsessed with very long walks and dream of doing them all over the world, wherever beautiful trails can be found. The idea of Rambling for weeks on end through fascinating landscapes and cultures absolutely lights me up.
What do you love about being a Sole Sister Rambler founder?
When I first began to consider inviting a few close friends to expand our little Messenger chat — called “Sole Sister Ramblers” — into a public space for others to join, I felt a huge wave of anxiety. I shared this with a friend, who said something I’ve never forgotten: “Sometimes anxiety and inspiration feel the same in your body. That swirl you’re feeling is part of the process.”
Not long after, I convinced my four co-founders to join me in creating what we thought would simply be a fun Facebook group. None of us could have imagined where that small idea would lead, how deeply it would resonate with women around the world, or the impact it would have on so many lives — including our own.
I am incredibly proud of what we’ve built and deeply grateful for the closeness it has created among us as founders, as well as with the many Sole Sisters I now call friends.
Sole Sister Ramblers is growing quickly and brings new challenges every day. But no matter what the future holds, I will always be proud of what we created together.
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