A Lonely Road to Nowhere, Article 2: The Beast

Up until about six months before my ride began, I had never even been on an overnight bikepacking trip.

I had ridden bikes as a kid, of course. And I used to ride my bike to class during college. But when it came to conversations about gear, mechanics, training plans, and all the other nuances of a long-distance bicycle tour, I was utterly clueless.

In the years prior to my ride, my mind had been focused on one thing: Work. I took any job I could get and did anything I needed to do to provide for my own needs.

The thought of going on a six months without an income sounded completely ludicrous to me.

It would be cool if I was some famous Hollywood actor’s kid or was raising money for cancer research.

But as a 31-year-old drifter with almost nothing to his name and no fallback options if he failed?

Yeah, that would be stupid.

Before starting my ride, I was probably worth around $50,000. That’s not my annual income. That was the grand total of my net worth at that time.

And yet, despite my practical side screaming at me to continue working and saving, this hare-brained bike ride was all I could think about from the moment I woke up in the morning to the time I went to bed at night.

I knew I wanted to do something like ride a bicycle cross-country. That sounded like the dream. But it was always just that: A dream.

Until it wasn’t.

Northbound

In April 2023, I quit my job in residential construction in the Colorado Rockies, loaded up my car, and moved north to Alaska.

It had been a lifelong dream of mine to buy land and build a cabin on it with my own two hands. Because what could possibly be more fulfilling than sleeping under a roof you built yourself?

My plan was to move to Alaska and work seasonally in the summer, then stick around in the winter and look for long-term employment.

Once I managed to secure a stable job, I would save as much as I could as fast as possible, then buy land and retreat into the Alaskan wilderness to build my cabin.

After years of searching for a stable job with good benefits, I finally found a work-from-home job in the marketing department of a telecommunications company in February of 2024.

I had been bouncing from place to place and job to job for years. I’d rarely had so much as employer-sponsored health insurance, let alone a full benefits package and the opportunity to grow within a thriving company.

Suffice it to say, I breathed a huge sigh of relief when I was offered the job.

I started work, met the team, and settled in.

After the first few weeks had gone by at my new job, my excitement over this whole “stable career” thing started to wan.

I wasn’t doing anything creative like writing copy, shooting promo videos, or developing a marketing strategy.

I spent most of my working hours editing customer notifications that someone else had written. By the time April rolled around, I found myself spending the bulk of my day staring out the window watching the snow melt.

One day, I was called into the headquarters building to attend the company’s annual all-staff meetings. During the meeting, all the big wigs got up to talk about the company's quarterly performance and its fiscal projections for that year.

I’ll admit, I struggled to keep my eyes open.

In the two years prior to landing my fancy new corporate job, I had worked at an Alaskan fishing lodge, a small construction company in Colorado, and a guest ranch in Wyoming’s Wind River Range.

I was used to spending most of my waking hours outside in austere natural environments. In my new role, the only natural environments I got to see were on my computer's desktop background.

Once the meetings concluded, I retreated to a small office in the headquarters building where I had set up shop for the day.

Almost as soon as I opened my laptop, I was bombarded with notifications, alerts about deadlines for tasks I had been assigned, and messages from my teammates.

My chest got tight, and it became hard to breathe. My palms grew hot and sweaty. The little office I was in felt like it had turned into a furnace.

I tried doing some breathing exercises to calm my nerves, but they didn’t change the fact that I had a ton of work to do and absolutely no time to do it.

All I could think about was sprinting out of the office. I wanted to escape. Fast.

But I didn’t sprint anywhere.

I spent the rest of the afternoon doing what I could to alleviate the pressure from my workload. By the time I clocked out, I was physically and mentally exhausted.

As I left the office that evening, it felt like I was speeding away from some beast whose sole objective was to rip my soul out and turn me into a walking corpse.

I drove home that evening in silence. I tried not to even think. But my mind couldn’t stop repeating one question: Where had I gone wrong?

I came from a middle-class suburban family. I had done well in school and hadn’t caused any trouble. I’d gone off to college and graduated in four years. Then I’d gone to grad school and successfully completed that program, too.

I had worked hard at every job I’d ever had – and I’d had a lot of them. I was a decent guy, I wasn’t too horrible to look at, and I tried to shower whenever I had the opportunity.

So, what was the problem?

Why had the stable job I had been searching for over the previous ten years of my life felt so…dissatisfying?

Big Purple Monkey

I quit my fancy corporate job the very next day.

When I logged off my computer for the last time, I stood up from my desk, took two steps over to my bed, and crashed down on it like a ton of bricks.

I didn’t have a back-up plan. I didn’t have any clue what was going to happen in my life. All I knew at that point was the thing that had been sucking the life out of me over the previous seven weeks no longer had me in its grip.

I let out a long, deep breath as I lay there staring at the ceiling.

As soon as my mind went still, a quiet voice inside me that I had been ignoring for a very long time screamed out four little words: “Go ride your bike.”

I bolted upright, and for the second time in as many days, my chest felt like somebody had clamped it into a vice.

I didn’t know it then, but that was the first time the tyrannical purple monkey known as Self-doubt popped out of nowhere and hitched a ride on my back.