Hi, I’m Jess, and I love life on two wheels.
Ever since I was 15, when I had the opportunity to go on a bike tour with a group of other teenagers, I’ve been hooked on exploring the world by bike.
These days, I love bike commuting around Louisville, where I live, as well as mountain biking and bike touring.
In 2013, I set out on a solo ride from the Oregon coast to the shores of Rhode Island, covering 4,200 miles in 80 days. I carried all my camping gear, stayed with generous Warm Showers hosts, booked the occasional motel, and relied on an incredible network of friends, friends of friends, and even colleagues of colleagues. It was, hands down, the best experience of my life.
So, why do it again? And why not somewhere completely different, like Europe or Asia? Honestly, I can’t fully explain it—it’s just a calling. This time, I’ll be riding the summer I turn 50, and while there are plenty of differences—the route, my age, and the organization I’m fundraising for—the desire remains the same.
What’s different this time? Well, for starters, I get to design every aspect of my trip—expectations, route, gear, and even my own “rules.” In 2013, I rode nearly all those 4,200 miles, accepting only three rides: one during a snowstorm in Montana (thanks to the California crew I rode with for a week and their sag truck!) and two short lifts from construction crews when the road was completely torn up. I also took a few ferries—across the Mississippi River, from New Jersey to Manhattan, and from Long Island to Connecticut. My goal then was to complete as many miles as possible by bike.
This time, the rules are a little different. I’m fundraising for an organization that means a lot to me, and I need to balance my ride with work and scheduled soccer matches.
My day job is running Cairn Guidance, a business I founded in 2006. Our mission is to create spaces where all people—especially youth—are healthy, connected, and able to reach their full potential. Most of our work focuses on adolescent health in school settings.
Another big passion of mine is futbol, soccer. Though I only played for one season as a kid, I’m a huge fan of the sport. A few years ago, I was invited to join a committee, which soon led to a seat on the Board of Directors for the LouCity & Racing Foundation. This role is the perfect blend of my professional mission—helping young people thrive—and my love for the game.
The LouCity & Racing Foundation is the charitable arm of Louisville’s two professional soccer teams, Louisville City FC and Racing Lou FC.
Their goal is to make soccer accessible to all kids, regardless of financial barriers, by providing programming, scholarships, and equipment across Kentucky and Southern Indiana. I’m deeply passionate about this mission, which is why I’ve chosen to dedicate my ride to supporting the Foundation.
My journey, Pedal to the Pitch, will take me from the East Coast to the West Coast, stopping at Louisville City FC and Racing Lou FC matches across the country. Unlike my 2013 ride, I won’t be taking the entire summer off—this time, I have a staff and will be working throughout the trip. I want to model what it looks like to pursue bold life goals while maintaining a work-life balance. I expect to ride around 4,300-4,500 miles, but with planned breaks, car rides, and soccer games woven in.
Because of the game schedule, flexibility is key. Weather, terrain, mileage, work obligations, and road conditions will all play a role in how the journey unfolds.
