A Lonely Road to Nowhere, Article 4: Should I Stay or Should I Go?

“I can’t go ride a bicycle from Alaska to Florida,” I said out loud in my bedroom/office. “I don’t have the experience, the gear, or the know-how.”

And it was true. I’d heard about people riding their bicycles insane distances – across the US, through North and South America, and around Europe. But those people were seasoned cyclists. They were bike aficionados.

I was just a kid who couldn’t figure out what he wanted to be when he grew up.

My brain raced through all the things that could go wrong. I could get hurt. I could break down in the middle of nowhere. I could get attacked by bears. I could get kidnapped.

Who was I to attempt anything like what I was caught up thinking about? I had no sponsors, I wasn’t raising money for a cause, and I didn’t have anything waiting for me at my arbitrary “finish line” in Key West, Florida.

But that was just it.

I wasn’t tied down by some job I couldn’t escape – I’d just proven that by quitting the only real job I’d ever had.

I wasn’t wrapped around anyone’s finger. I wasn’t shackled to any debt payments. I was 100% free to go where I wanted and do what I pleased.

So, why did I still feel stuck?

My reservations about embarking on my ride weren’t primarily because of my lack of know-how. They stemmed from a complete and utter lack of self-belief.

I wanted to be and do everything I could all at once.

Astronaut. Archaeologist. Musician. Writer. Film producer. Academic. Philosopher. Businessman.

The list went on and on forever. Ever since I had committed to living debt-free during covid, I had been crippled by indecision because of the overwhelming possibilities around me.

I was willing to work. But for what? What was the one thing I needed to do that would require me to sacrifice everything else?

The answer slapped me over the face the day I quit my job.

I was going to ride a bicycle 6,000 miles from Alaska to Florida without any cycling experience. It was April 2024. I intended to depart on my ride that May.

Slowing of the roll

Minutes after quitting my job, I texted Dave, my former manager at the Alaskan fishing lodge I had worked at the previous summer, to inform him of my bike ride plans.

I met Dave on my first day in Alaska. Like me, he was from Nebraska. Unlike me, Dave knew a lot about bikes. He and his wife had embarked on several long-distance bike rides throughout their lives.

I also texted my friend Harrison, a shaggy-haired tour guide at the same lodge. Harrison was a former stand-up comedian and larger-than-life character who had completed his own ride from Fairbanks to Key West in 2014.

Dave texted me back a few minutes later saying he could offer me a job at the lodge for another season so I could save up and go on my ride in 2025.

As soon as I saw Dave’s text, I rejected the idea. I had been waiting long enough. It was now or never.

Or so I thought.

Harrison also got back to me moments later. I asked him how much preparation he did before beginning his ride. Instead of listing out his entire training regimen and all the equipment he'd had with him, Harrison said the very thing I needed to hear.

He said, in about as many words, that he mostly just figured things out as he went.

That was the green light I needed.

Then Dave texted me again saying he could chat with me in greater depth on the phone a few minutes later.

Waiting

I waited patiently by the phone as I thought about what I would need to buy, and when.

First off, I still had to get a bike.

The only one I had was a janky mountain bike I’d bought from someone on Facebook Marketplace before leaving Colorado. I didn’t want to ride that piece of junk across North America.

Then there were the bike racks and the bags. I’d seen a few bicycle touring setups, and everyone seemed to do things slightly differently. How was I supposed to know what would work best for me?

And of course there was the camping gear. I’d been camping since I was a kid, so I was confident in my survival skills. I had also accumulated most of the outdoor gear I would need, too. So that much I didn’t have to worry about.

Besides gear, I needed to think about my plan. More specifically, my route and my timeline. All I knew at that early stage was that I wanted to ride from as far north as I could get to the southernmost point in America. Besides that, I had no other agenda.

I planned on taking the ferry from Alaska to the Lower 48, then making a diagonal across the states from Washington to Florida. I figured it would take about 4.5 months.

It would probably cost about $10-15,000. And I would set off in less than a months’ time.

While I was making all these calculations in my head, Dave texted me again saying he was free to talk.

I called him immediately.

“So, you have a big ride ahead of you,” Dave said. I told him I did, and I didn’t have much time to prepare for it.

He paused.

“Y’know, you can come back to the lodge and work if you want to. You’d have more time and money to get ready that way.”

It was my turn to pause.

I didn’t want to wait. My whole life had been a waiting game. But still, I hesitated.

Dave remained silent on the other end of the phone.

And then I heard the words tumble out of my mouth before I knew what was happening: “If the job offer is still there, Dave, I’ll take it.”

“Sweet,” Dave replied, in his usual calm manner. “We’ll be happy to have you back.”

We hung up shortly after that. For the second time in the span of an hour, I crashed onto my bed. A huge breath flowed out of my body.

I texted Harrison saying I was coming back to the lodge for another year. He responded with some well-wishes, but I envisioned him laughing and shaking his shaggy head as he read my message.