The Joy of Rediscovering Yourself on the Open Road
How a low-tech road trip two decades ago is the antidote to finding joy in an always-on digital world
This post is the second in a series of three essays produced through David Perell’s Write of Passage Bootcamp. I joined cohort 13 as one of ten O'Shaughnessy Venture Fellows and look forward to injecting ideas and innovations from the program into The Jaunt newsletter. Thank you so much for supporting my writing!
I’ve never been so scared to do something in my life.
There I was, bent over the side of my Land Rover, dry heaving onto the pavement of a small-town Wisconsin street named after a founding father.
Each wretched convulsion summoned my belly. Emptiness. Nothing came.
I was leaving everything I had known, a childhood growing up in a small farming town. Except for a short stint at college in “big city” Milwaukee, the agricultural landscape of Southeastern Wisconsin was all I had known.
Now, my heart was seeking something different. Something bigger. I wanted to go West. I wanted to carve out a niche doing film and writing.
So, there I was in the winter of 2003. Saying goodbye to my family and a college girlfriend.
I packed all my earthly possessions into my truck and departed Elkhorn, Wisconsin.
Driving westward, my only distractions were whatever AM radio station I could snag from the atmosphere, lonely country songs, and saccharine pop melodies hurtling across the prairie by a series of ghost repeaters.
My destination: San Francisco.
I cried most of the way to Moline, Illinois. I grasped whatever tangible audio waves of nostalgia were transmitted on the radio from my home state. As I pushed closer to Iowa, the last vestige of traffic and weather reports from my home state fluttered into obscurity.
It wasn’t until I saw Interstate 80 cross the Mississippi that I gathered my faculties. Only then could I focus on the gravity of my situation and ponder a new life on a stretch of highway that made its progress across gentle farmland, rolling patchwork quilts of crops, and eventually to the jagged peaks of the Rockies.
Given the ample connectivity we hold in our hands and pockets today, it’s almost astonishing that I completed the journey. I had as much phone signal as the pioneers who trekked across the forbidding land in wagons to a better life.
I had just joined the legions of newly mobile-connected people, and my shiny flip phone accompanied me. It sat idle in the cup holder. It could only imagine a world of endless signal strength and non-existent call drops. Or that it would be replaced by a more powerful device in a few short years, relegated to the dustbin of history in favor of tech connectivity.
I was an astronaut hurtling through space—just me and my trusty four-wheeled satellite. Lulled by the orbit of lonely I-80, I was just a beam of headlights hurtling into the sunset. All contact was cut. I was out of touch with Mission Control.
There were only memories.
No selfies. No snapshots. No reels.
There were no digital artifacts.
No Facebook posts. No Google Reviews. No Tweets. No threads.
There were no social pressures.
No likes. No Retweets. No comments or shares.
Long before the advent of podcasts, the only in-car entertainment was AM news radio or the twang of country stations. At night, the voice of Art Bell provided the soundtrack of the ride-sharing stories of cryptozoological beasts and UFOs as the car pierced through the nighttime.
Yet, somehow, despite the lack of devices and technology to capture the trip, I still vividly recall so many moments that were stitched together over the course of the two-day journey.
I recall the color of the sunset. I recall the gas station I slept outside on the outskirts of Omaha, Nebraska. The not-at-all-tasty coffee from a middle-of-nowhere joint in Wyoming. How the snow cut through the parking lot lights of a casino parking lot in Winnemucca, Nevada. How the air smelled distinctly in California of mountain pine. I will never forget how the light looked different in the Bay Area, like something from a film.
Most importantly, I could simply and unequivocally ponder the endless possibilities of a new life and a new place to live. Nothing clouded my thoughts. There were no distractions—no calendar invites or emails to check. I was permanently out of office and riding high at Inbox Zero.
I made it to San Francisco, staying for more than a decade. I went to graduate school, got my first post-college job, and witnessed the low-tech version of myself grew into the high-tech version we’ve all become. I watched with wonder as mobile devices, tablets, and apps profoundly changed the way we exist. Primarily for good, but now most likely for the worst.
Nearly twenty years later, I’ve reached the point of tech saturation. Most of my adult life has been recorded, a catalog of geodata and pixels filed away in massive data warehouses in far-flung places.
Ironically, my brain requires vast effort to conjure them into existence — a series of zombie-like motions driven by my fingers and thumbs as I pin down moments on a photo timeline on my phone. But that trip across the country back in 2003 can be recalled in a nanosecond. So many memories come flooding back, transporting me to the low-fi version of my younger self, unaware of the cataclysmic tech hurtling towards me in a state of childlike wonder at the thought of the unknown waiting for me.
To Roam Again. To Feel the Joy of the Open Road. To Rediscover Ourselves.
It’s almost impossible to describe the insurmountable joy I feel every time I’m on the open road.
Driving is always magical – cinematic. Partially because there is a simple joy in going somewhere new perhaps, but also because it can be a time to unwind, contemplate, and pontificate.
The yellow hash marks morph into a cement celluloid story – a movie with no beginning, middle, or end – as infinite as the ribbon of highway.
The passing scenery is the stuff of million-dollar Hollywood setpieces. Roger Deakins has spent his career reconstructing the things you can see out your windshield.
When I’m driving, I feel like the director of my own shots - my eyes the camera scanning the horizons for the wide, establishing shot. When I’m driving, I am also the screenwriter – the architect of my thoughts.
But for most of us, the film has ended. Somewhere in the last decade, the joy of driving has disappeared.
Many of us drive to work, to tasks – the drudgery of things we need to check off a list encumber the simple pleasures of just being in the moment.
Once you take off your goggles, you’ll be amazed at your newfound sense of joy, wonder, and discovery.
The perfect antidote is to tap into that low-tech version ourselves and escape for a spell. Toggle off the connectivity of life, sidestep digital habits, and tap into the antiquated means of acquiring dopamine on the open road – just you, your thoughts, and endless possibilities.