You can’t make this up.
On Friday, May 8th, 2026, a few miles outside of Jamestown in Charles City, along the Virginia Capital Trail, I met a cyclist named John (Hope on Two Wheels). He was at the very beginning of a journey that would carry him across America to Astoria by way of the legendary TransAmerica Bicycle Trail.
As we talked, I realized how strange and meaningful timing can be. In 2019, I had ridden this same stretch of trail approaching Jamestown from the opposite direction, nearing the completion of my own cross-country journey. Now here was John, filled with anticipation and excitement, just beginning his.
I asked him how long he had been preparing for the ride.
“Two years,” he answered.
Immediately, I thought of another John, John DeGregory, I had met back in 2022. This John had discovered my story while researching riders from the Trans Am Bike Race and eventually found Forty to Finish. We exchanged messages (He lived in California. I lived in New Jersey) and I gladly shared my time, enthusiasm for the moment, lessons learned, and answers to the many questions that come before taking on a life-changing challenge.
Then, in August 2024, I surprised him at the finish line when he arrived at the Yorktown Victory Monument along with a fellow racer Tim Barrett, watching them complete a dream they once only imagined.
Fast forward to May 8, 2026, and there I was again, offering John (Hope on Two Wheels) a few words that helped me during my own ride:
Stay positive. Don’t think about the 4,200 miles ahead. Focus on the next 10 miles. Then the next 10 after that.
As fate would have it, the day still had one more story to tell. While spending time in Charles City, I struck up a conversation with a volunteer at a rest stop for the annual Cap2Cap cycling event. In a way only life can arrange, another connection soon revealed itself.
Life is a mosaic of chance encounters, unexpected conversations, and moments that quietly shape us. Too often, the only thing standing between us and a meaningful experience is the decision not to step forward and see what’s waiting behind door number “live life.”
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