In the summer of 2006, I set out to ride my bicycle solo and self-supported around the perimeter of the United States. Before leaving, a friend who had been an integral part of helping me plan the trip handed me a pocket-size journal, “For your memoir,” He said with a hug. While I had never considered writing a book, I journaled every night of my ride, recapping interesting and often odd interactions with strangers.
After the trip, I attempted to piece together my journey at least a dozen times. One of the problems I faced in completing the work that became Headwinds was deciding what kind of book it should be. As I was preparing for the trip, I searched desperately for any book about long-distance bike travel, but they simply did not exist. Now, on the other side of my own trip, I thought there was an opportunity to fill that space. I set the project aside and every few years I’d flip through my journal, open a document, and take another half-hearted stab until I let either self-doubt or indecision get in the way.
In the 14 years between completing the trip and writing Headwinds I’d find myself in social settings where someone new would learn about my summer in the saddle. They’d inevitably ask for my favorite story and, tired of always retelling about my accidental night at a nudist colony, I’d start to mix it up. More and more vignettes would make their way into the rotation. Like the time a cop pulled me over riding on the shrinking shoulder of the 101 trying to find the Golden Gate Bridge. Or about how I basically fueled my body on gas station fruit pies and McDonalds for three months. I often wondered if I could just tell the stories from my trip in a voice that made my friends and family feel like I was reading to them?
In the fall of 2019, I found myself at a sort of perfect storm for picking the project back up. I was feeling burned-out building software and was moving to Berkeley, CA from Detroit, MI with enough savings to support myself for a few months. I decided now was the time to finally put pen to paper and stick with the process through to the end. Instead of overthinking what kind of book I should write, I planned to simply take the project on day by day. I hoped that if I got the stories out of my head and onto paper, the type of book it should be would reveal itself.
For the next seven months I sat down daily, journal in hand and wrote. With a surprising frequency, details of the trip that I had long forgotten but had written about in my journal came vividly back into view. As the page length increased, I grew more confident that I was capturing the details of the trip as they happened, not just how I wanted to remember them.
As I’d hoped, eventually it became clear that I was writing a memoir, but that presented a terrifying prospect. Memoirs, as I thought of them, are often memorialized accounts of a life or event in which the reader should draw meaningful lessons. Did my bike trip qualify? I was fairly sure it didn’t, but since I was both making real progress and enjoying the process, I continued writing.
At some point, a few themes started to bubble to the surface. Some were obvious; the kindness of strangers, physical challenges related to riding a bike around the country, and equipment failures. These themes were objectively easy to recount. Two others weren’t quite so straightforward. I stayed with dozens of host families on the road, many of whom didn’t share my world view, particularly around matters of race and religion. I knew I needed to include these sometimes-painful encounters in an honest way, trying to encapsulate what was said, but being cautious to avoid a preachy tone. In these scenarios, I tried to leave space for the reader to evaluate the situation.
Another obvious theme that was difficult to explain but led to the spiral of emotions towards the end of the trip, was my deep loneliness. As somewhat of an introvert, I didn’t know what to make of my longing for social interactions with familiar faces and the feeling of a cartoonish storm cloud hovering overhead for hundreds of miles as I pedaled along. Having never faced such depression, it took a long time to diagnose the problem. Writing about that emotional response was my greatest challenge through the project. I had to learn to be vulnerable as I recalled sitting on a curb on the outskirts of Phoenix, watching a puddle of my own tears evaporate in the desert heat.
Headwinds doesn’t have a tidy ending that you might expect from a book about a bike trip. Spoiler alert. I called it quits before making the full lap around the country. For many years, a sense of shame for not completing the loop prevented me from fully sharing my experience. I was afraid people would view the trip, and me, as a failure. Some people still might, and that’s ok. In the end, I’m proud of the final version. What I came to realize through the writing process is that not all adventures wrap up in the way that you might have intended, but it doesn’t mean there weren’t lessons and stories worth retelling.
In that aspect, Headwinds turned out to be a memoir, but not one that aims to impart wisdom on its readers. Likewise, I never intended the book to be the culmination of a life well-lived. I set out to share my stories from that summer, finding the changing landscape of the country and myself as a then 24-year-old man pedaling a bicycle. If someone takes something away from my experiences that they can apply to their own life or spurs a conversation with friends, that’s great. But if all they do is laugh at my junk food diet and feel a tug on their heart strings at my descriptions of teary-eyed calls home, I’ll have done my job.
Landall Proctor is not a New York Times Bestseller, but if enough of you buy this book, he’ll happily update that sentence. So really, that’s on you. And your friends. And their friends. When he’s not writing about his bike trip he likes to race marathons, bird hunt with his dog George and say things that result in eye rolls from his son, Hudson. He lives in Berkeley, CA and thinks it's nice. You can find Headwinds and read more stories that didn't make the final edit here.
