Six Months. 7,000 miles. One Clueless Bicyclist.
- Tim Bolton
- 1 day ago
- 6 min read
When people ask me why I decided to embark on a 7,000-mile bicycle ride across North America in 2025, I like to smile at them politely and feed them a bald-faced lie.
I typically tell people I went on my bike ride because I’m young, single, relatively healthy, and am not tied down to any one place. If there was a time in life to travel the world, it was now.
All those facts are true about me. But they’re just facts. They’re not reasons someone decides to ride a bicycle for six months.
The real reason is much more convoluted.
The Starting Line
I showed up to my bicycle ride a 31-year-old drifter, unremarkable in virtually every way. I was searching for direction. Any direction.
I needed some sort of foundation or roadmap for just “doing life”. In the years prior to my ride, I had moved countless times and worked numerous jobs across a variety of industries. And most of that period I was living at or near the poverty line.
Early on in 2024, I had finally found a “professional” job in the marketing department of a telecommunications company.
After so many years of job-hopping and moving around, I had found a position that offered good wages, great benefits, and an upward trajectory within a stable industry. It had all the ingredients you could want in order to build a respectable career.
I lasted seven weeks at this supposed “dream job”. And I felt an overwhelming sense of relief when I decided to walk out the door.
I had zero interest in the work I was doing. I had hardly ever given a passing thought to the telecommunications industry in general. But after so many years of wandering through a kind of professional purgatory, I was enamored with the idea of finally having stability.
I didn’t have a backup plan when I quit. I didn’t have any plan at all. But while I sat in my home office staring out the window during my last few days on the job, one idea kept nagging at me that I simply couldn’t get rid of.
What if I rode a bicycle from the northernmost to the southernmost points in the continental United States?
And what if I did it alone?
Stumbling Out of the Gate
There was one major problem with this harebrained idea that had popped into my head as I was daydreaming at work: I knew basically nothing about bicycles.
I’d never gone bikepacking. At that point, I’d never ridden a bicycle for more than a few hours at a time. And I wasn’t skilled at doing even the most rudimentary bike maintenance.
But in the days and weeks following my decision to quit my job, I determined that I really had only two options moving forward:
Option A: Keep doing what I’d always done and travel further down a directionless path to nowhere.
Option B: Turn around and face the inner critic who doubted me at every turn.
Because through all my years of wandering, my problem was not a fear of commitment. My biggest problem was a complete and utter lack of self-belief.
Coaches and Cheerleaders
I moved to Alaska in the spring of 2023 to work at a fishing lodge on the Kenai Peninsula.
Within the first week of my arrival, I met two other people who had embarked on their own long-distance bicycle tours years previously.
The first was a tour guide at the lodge. He’s a shaggy-haired ex-stand-up comic named Harrison who is filled with personality. He had ridden his bicycle from Fairbanks to Key West back in 2014.
The second person was Dave, my manager. I’m convinced that Dave knows some things about pretty much everything, and everything about some things. One of those things is bicycles.
Both of these men gave me invaluable advice during my ride preparations, but there was one piece of advice they gave that helped silence the self-doubting voice within me.
They both said, essentially, “You figure things out as you go.”
Hurdles and Roadblocks
And so, over a year after quitting my job, in the spring of 2025, I embarked on a two-week training ride from Homer, Alaska, to Fairbanks. Then I flew up to Deadhorse as far north as you can get on Alaska's road system.
And I spent the next six months figuring out:
A thousand ways not to patch and change bicycle tires and tubes.
How much gear I should not have carried with me on the journey.
That mechanical breakdowns, while incredibly frustrating and expensive, really aren’t the end of the world; they’re just part of the journey.
That sleeping under the stars beats pitching a tent night in and night out.
That most people are willing to help a cyclist stranded in the middle of nowhere.
That accepting help – in the form of water, food, money, friendly company, and even a car ride into the nearest town – isn’t a sign of weakness. It’s a sign that I’m meant to exist in community just like everyone else.
There were certainly days that offered bigger challenges than others.
On my first day in Canada, the bear can that I had just filled with food went missing, and I was several days of riding from the nearest grocery store.
I also crashed my bike into a curb while riding down a hill outside Vancouver, Canada, in early August. I didn’t find out I had broken a bone in my right thumb until a month later as I passed through the Bitterroot Valley in Montana.
My thumb would remain in a brace for the next 3,000 miles as I rode across the Lower 48.
Only after completing my ride did I discover that I had torn a ligament in that thumb in addition to breaking a bone, and I would need to have surgery to finally replace it over six months following my crash.
Crossing the Finish Next Starting Line
Despite all these setbacks and hard lessons learned, on November 12th, 2025, I rode into Key West, Florida, on a picture-perfect island day. I arrived on the island almost exactly six months after starting my training ride on May 15th.
When I finally rounded the last corner and the southernmost point marker came into view, several emotions swept over me.
Elation was one. Exhilaration was another. Relief was a third.
But the word that stuck with me most and wouldn't let go was "culmination".
Reaching the southernmost point marker was the culminating moment when all the work I'd done since quitting my job in the spring of 2024 melded together to form me into something new.
My bike ride was not just a bike ride. It was the rite of passage I needed to embark on to become the person I was meant to be all along.
A New Ride
The true reason I went on my ride was to silence the voice inside my head telling me that no matter what I did, it wasn’t enough.
Because throughout my life, that voice had told me that I wasn’t enough. I needed to do more, get more, be more.
And so, for ten years, I went down the path towards “more”. And all it did was solidify my belief that I was less than.
My bike ride was the antithesis to my pursuit of more. It redirected all my energy away from accumulation and towards contribution.
The culminating moment when I hoisted my bicycle above my head at the southernmost point meant more to me than simply arriving at a destination. Those final moments of my ride south became a personal point of delineation.
No longer was I simply following a path in the hopes that it would lead me to some unseen, unknown place I’d never been before. Instead, I had taken agency and done something whose only requirement was that I kept showing up.
Somehow, despite my lack of self-belief through all the mishaps that occurred during my ride, I managed to follow Harrison and Dave’s advice. This unremarkable guy who couldn’t hold a steady job managed to figure things out as he went.
I didn’t have much money when I started out. And I barely had any cycling experience.
So the question I want to leave you with is simple: If an unremarkable guy and a novice cyclist who couldn’t trust himself to change a bicycle tire properly could face and overcome all the challenges I’ve described here, then why can’t you?
Time is ticking. None of us knows how much of it we have left. So who do you want to be when your hourglass runs out of sand?
Decide on your own answer, and then hop on your metaphorical (or perhaps literal) bike.
And ride.
