Q: What's the hardest thing about biking across America with 10 guys?
A: Planning it!
This past Spring, I rode across the country on a bike with ten friends. People have asked me about this experience, curious to know what I gained from it and what the highlights were. It was a 14-day expedition from San Diego to St. Augustine, Florida, filled with adventure.
The real story, however, begins with how this whole thing came to be. Convincing ten guys to mark off 14 days on their calendars in April, right after spring break and just before the summer kicked in, was no small feat. There were school activities wrapping up, family commitments, work obligations – the list goes on. Yet in November, we managed to get everyone on board and committed to those dates.
In some ways, it felt like a game of chicken – who was going to cancel first? No one did.
As the trip rapidly approached, things were incredibly busy in my life. My kids were right in the middle of Little League season, school was drawing to a close, and my wife Sarah had her own commitments. On paper, it wasn't the ideal time to embark on such a journey.
So, the biggest takeaway from this experience is the power of commitment.
Life is always going to be filled with reasons to say no. There’s always something coming up, and there are always going to be concerns about safety, cost, risk, and potential danger. Yet we chose to say yes, and that decision is what made the trip a reality.
Even so, as the departure date drew nearer, I found myself questioning the decision. The weight of responsibility and the fear of being far away from my family and duties back home began to creep in.
Two days before we were set to leave, I was contemplating canceling the entire trip, suggesting that we could bike around Central Park for five days instead.
That way, I reasoned, I'd be closer to home and could easily fly back to Atlanta if needed. I even tried to sell this idea to a few people, highlighting how it would allow more people to join us and reduce the perceived burden of responsibility. But the response was a unanimous and resounding "No."
"Jesse, it’s on the calendar,” someone said.
And then I knew.
We made a decision, we put it on the calendar, and now it was time to push aside the fear and embrace the responsibility that came with our decision. We were committed to it, and there was no turning back.
So, what did I get out of biking across America with ten guys?
A whole lot of lessons, unforgettable memories, and the profound understanding that sometimes, you have to say yes, put it on the calendar, and then commit... no matter what your fears are telling you.