I Loved Bike Touring—Until I Got Paid to Do It

I Loved Bike Touring—Until I Got Paid to Do It Outside

In a race for your life from a belligerent madman, there is no worse getaway vehicle than a recumbent bicycle. Particularly on any sort of climb. At least that’s what Alan* and I discovered as we crept up a desolate stretch of Arizona highway, necks craning behind us to see if the knife-wielding drunkard was gaining any ground.

Alan, an amiable psychologist in his late sixties, was the one turning his recumbent’s pedals as fast as he could. I was on a traditional bike, but as the leader of this group tour across the U.S., I was duty bound to ride at the back, to help with any mechanical issues.

Not today. Today Max rode at the back. I could see his neon jacket a hundred yards behind us, from where he was trying to close the gap. An hour earlier, from his perch on a picnic table at the edge of the sad RV park we’d called home for the night, he unceremoniously announced his plans to murder us all. It was 5 A.M., and he was on his second 12-pack of Old Milwaukee, having never unloaded his bike nor set up his tent the night before. Instead, it seems he’d visited the town liquor store while we slept. Crushed beer cans formed a barrier reef around the table. Something in the morning chorus of sleeping bags being unzipped had stirred Max’s drunken rage into action. Red-faced, he barked obscenities and sexual slurs, most of them at me. And then came the death threats. Bleary-eyed and not yet caffeinated, I scanned the empty horizon for anything resembling a cell tower and the possibility of a phone signal. Then I took the only course of action available to me: I politely requested that he leave the tour.

Now we were engaged in the world’s slowest chase scene with a middle-aged psychopath in high-vis spandex. The rest of the tour’s participants, a ragtag band of 16 cyclists from all over the U.S., had long since hightailed it from camp to tackle the day’s first climb. I was out of water and in need of coffee, and my stomach was growling a song about pancakes. But Alan and I kept pedaling, determined to die somewhere more scenic than the side of a baked desert highway, next to an empty bag of Cool Ranch Doritos and the dried-out remains of an armadillo.

It was March 2009. We were just eight days into a guided cross-country bike tour, and things had already started to unravel. The trip, run by a national bike-touring organization, would take us from San Diego to the coast of Florida over the course of two months. Each day we’d pedal anywhere from 50 to 80 miles. Each night we’d set up our tents at campsites along the way. But things had gone sideways from day one, when a young man who’d suffered a severe brain injury in a motorcycle crash years before showed up to tackle the ride on a rusty singlespeed cruiser. When I questioned the soundness of the bike, his mother stabbed her finger in my chest and said, “He can do anything he puts his mind to.” The frame snapped into two pieces that afternoon, one mile into our prologue ride. I scrambled to find him a replacement in time to remain on the tour.

At some point during the first week, I stopped thinking of the group as a band of fellow adventurers and more like cast members on a partially scripted reality show designed to bring out the worst in everyone. This morning hadn’t been the first hint that Max was cast to be the angry one, or, in reality-TV parlance, the one “not here to make friends.” Earlier in the week, he’d uncapped a fire hose of rage-fueled expletives the night sprinklers came on underneath his tent. Out of shape and unable to keep up with the other riders, he’d allowed his exhaustion to slide into simmering resentment that escalated into a brawl with a sprinkler head. But today was the first time he’d threatened violence against anyone in the group.

He was hot on our wheels, with a multitool and nothing to lose. Had anyone considered running background checks on any of these people?

Believe it or not, bike touring had once been my greatest love, and not just the conceit for the survival-based elimination show I now found myself living. Four years earlier, when I was a somewhat adrift 25-year-old bike messenger, I’d left my home in Portland, Oregon, for a 2,600-mile ride to Missouri with a bunch of used camp gear and a ratty T-shirt that read, “Two Wheels, No Rules.” My body felt electrified with possibility as I rolled past the Portland city limits, ready to chase some vague spirit of adventure I felt had long been denied me by the canon of great road-trip novels that only told stories about men.

The things I experienced on that trip—the beauty and bleakness of small-town America, the awe of pedaling up and over a mountain range, saddle sores that crippled my romantic life for half a decade—changed me profoundly, in ways I never expected. Months of having no one to talk to except for elderly roadside gawkers brought out a gregarious, assertive side I didn’t even know I had. I left Portland a painfully shy queer kid with disheveled hair and a distrust of strangers. I came back wiser, bolder, more openhearted, and with even messier hair.

But returning to the monotony of daily life was like quitting an antidepressant cold turkey. I spent the next six months in an adventure-come-down fog, broke and dreaming of my next touring fix. My once thrilling job as a messenger no longer felt fun, dangerous, or freeing. It had become as predictable as a morning paper route.

On the road, I pedaled all day and wrote in my journal into the night, detailing my misadventures by the glow of a headlamp inside some of America’s sketchiest campsites. Each day was different and surprising. Would I find rustic, shaded forestlands to sleep in, or an abandoned Lions Club park by the side of a seven-lane interstate? Might I encounter a smooth, winding descent alongside a river, or a series of 19-percent-graded climbs guarded by feral pit bull mixes? How long could the human body subsist on peanut butter and banana sandwiches alone? Better yet, how long could I continue to go without showering before being added to some sort of national-parks watch list?

Back in Portland, dreams of the open road haunted me. The mountains. The desert. The crush of gravel under my tires. The satisfaction of tracing my finger across a map and realizing my legs could take me anywhere, given enough time and carbohydrates. Even the memories of waiting hours by truck-stop pay phones for my girlfriend to call me back struck me as timeless and romantic. As I shuttled documents to and from law offices and courthouses, I mentally relived those long, sweeping downhills and misty forest back roads—basically, I fantasized that I was Jack Kerouac with a helmet mirror.

It was while deep within this state of longing that I found myself susceptible to some truly bad baby-boomer advice. Not of the “Go back to school and get a degree in something practical” variety. That would have been helpful. This was more like an empty platitude someone’s mom might’ve been wowed by because it was delivered by a charismatic stranger sitting next to her on a plane.

OK, it was my mom. She called shortly after her flight landed, eager to share.

“Do what you love and the money will follow,” she said.

It was one of those nuggets of wisdom you only hear from people with monetizable assets—or the right ratio of talent, luck, and privilege to have landed a dream job that actually came with a paycheck. But in the swampy darkness of a Portland winter, the idea resonated. I adopted it at face value. There had to be a way I could get paid to keep hauling everything I owned across the country by bike. After all, I didn’t need a lot of money to follow from doing what I loved—just enough to support my cat while I searched for America out on the open road. That spring of 2006, I signed up for a bike-touring leadership course.

Being an outsider in the touring world would work in my favor for landing a job. I was young and female in a scene dominated by kind-eyed, gray-bearded men in zip-off cargo pants. I came to the course preloaded with my funniest bike-messenger anecdotes and a talent for Lightning-fast flat-tire fixes. A month later, I was offered my first gig leading a tour...

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