On The Road…again…and again
Three readings of Jack Kerouac’s influential masterpiece
In my 20’s, like many a wayward, wanderlustful youth, I found my way to Kerouac.
Born, raised, and schooled in the greater Boston area, when I graduated from college, my Bachelor’s degree in hand, I itched for adventure. There was so much world out there, and I had seen so little of it. I was discontented with the life I’d known to that point, with the responsibilities of adulthood that were about to be heaped upon my slouching shoulders. I felt fettered, and I chalked up place as the primary factor of my imprisonment.
Enter Kerouac.
The first time I read On The Road I was 22 years old. And, like so many before me — On The Road became the holy book of adventure, the text that justified exodus, the blueprint for that ideal life of wandering and wayfinding. I recognize the cliché, but such was the nature of the Beat generation. They, too, were lost; they, too, raged against the machine. In all my youthful idealism, I concocted a version of my life that mirrored Sal Paradise’s quest for meaning and self-worth.
And sure, I was not trying to model Kerouac’s adventure exactly. I had no Dean Moriarty (Neal Cassady IRL) deviling on my shoulder, no appetite for odd jobs and flighty romance. I had no mentors strewn about the country. And I certainly had no desire to hitchhike. Yet I still dreamed of being part of a counterculture. I visualized lugging my guitar around the country, playing dive bars, sleeping on couches. I imagined joyriding in Cadillacs (although maybe at slower speeds), unraveling the mysterious of the universe and plotting a new way forward. I imagined diminishing destination and embellishing journey. I imagined New Orleans, Denver, and San Francisco in all their extant glory. I imagined carefree revelry. I imagined.
Fast forward five years.
I am 27 years old, and was (mostly) still not living a Kerouacian lifestyle. I was, however, happily married (check) and living in Hawaii (check), so life was pretty good. And yet I still longed for something. This was undoubtedly tied to my lack of career satisfaction. I had found myself in the retail world, which, though beneficial in many ways for many people, was not my calling. I still yearned for more. I wanted to explore. I once again (inaccurately, this time) blamed place for my discontentment.
And what a short-sighted fool I was
Re-enter Kerouac. In the previous five years, I had read very little. My nights were dominated by sitcom re-watches, guitar noodling, and general exhaustion. And while I remembered the general gist of OTR, many of the details had faded. I was young when I had first read it, tired, distracted. I hadn’t read it well, or closely. I picked it up again, hoping to lose myself in the text that has become a paradigm of escapism: as Kerouac himself escapes, so do we.
I re-read On The Road at 27, and it all came flooding back: all the hope, all the promise. In my mind, though I’d aged, I believed that I was not yet so old, believed that there was still time. And no, I still did not want to hitchhike, nor did I crave the unconcerned Beatnik debauchery and promiscuity. Mine was a locational pining.
Thus began my true Kerouac phase. At 22, I reflected, I was still too young to understand, too ignorant of the hows and the whys. At 22, I’d known no real responsibility. At 22, there was nothing but horizon, and I had squandered it, becoming lost in the local and the present. But it was not too late. Armed with perspective, I chased that ideal. I became obsessed with Kerouac, his prose, his oeuvre. I think I believed that if I read him enough, I could perform literary alchemy and turn his romanticized vagrancy into actualized living. I read Desolation Angels, Big Sur, Dharma Bums (which became my favorite of his novels) and even his eponymous biography (written by Ann Charters). I searched him out, visiting Big Sur myself (pictured below — which everyone should visit, Kerouac fan or not), and even poked around City Lights Bookstore in San Francisco, where Allen Ginsburg first read/performed “Howl,” a moment Kerouac depicts in Dharma Bums’ frenetic opening pages. Though I was now living in San Diego (check) and was still happily married (double check), my then-career in retail weighed on me heavily. And so I chased that Kerouacian ideal, believing that his truths lay just over the next of San Fran’s rolling hills.
2019.
It was time to move home. My wife had finished her Masters of Nursing (which is why we were in California in the first place), and we had decided our four year out-of-state adventure was over. Our time away from Massachusetts had been wonderful, cathartic. We learned so much about ourselves, about what was important to us. And moreover, I’d found a new direction — I’d been accepted to a graduate program for teaching (a choice that has paid immense personal and professional dividends). We decided that we would make the most of our work hiatus and take an extended cross-country road trip home, a two and half week odyssey that would take span nearly a dozen cities and during which we would see numerous friends and family. Yes, we were going on the road. And so it felt only right that I should revisit Kerouac a third time.
I read On The Road for the third time at age 30, and what I found was…confusing?
Yes, much of the idealism still existed, and nothing had been lost from his expansive, brilliant, “spontaneous prose,” but it was now colored with the dull palate of pragmatism. The vagabond existence that I once thought to be within reach had cracked and split, its splinters lodged in my outstretched fingers. That romanticized way of life as seen through the lens of adulthood now felt empty, lacking. The glorified reverence of Sal Paradise towards his friend and co-roadtripper, Dean Moriarty, read as sycophantic and misguided. The saturnalian lifestyles of Sal, Dean, and their Beatnik comrades now seemed pitiful: it was no counterculture; it was the vacating and denial of responsibility. As Ann Charters notes in her biography, Kerouac was, definitionally, homeless. Quite literally, he never had his own home — at least not for very long — but rather jumped from city to city, from couch to couch, only stopping long enough to document the swirling, diaphanous world around him.
What is fascinating and generally unknown of Kerouac’s novels is the latency between the stories of the texts and their publication. It is a testament to his craftsmanship that he makes you believe you are riding right alongside him, that his “spontaneous prose” did in fact happen spontaneously and not in reflection. Kerouac’s life was always one phase further than his novels depict. In considering him, he almost becomes a personified version of the particle in the Heisenberg’s Uncertainty principle: we cannot know both his position and speed at the same time — the more we try to discern where he was, the less we understand how fast he was moving.
In documenting that very same counterculture, the incomparable Joan Didion named her essay collection Slouching Towards Bethlehem, an allusion to W.B. Yeats’ indelible “The Second Coming,” a poem that is, at its heart, about entropy. In theoretical physics (in keeping with the theme of the previous paragraph) “entropy” suggests a gradual decline from order to disorder. Such were Didion’s feelings about this generation of rebels, of Kerouac and his lot. Try as they might have, their centers would not hold. And Kerouac was, in so many ways, the poster child of the Beatnik generation. A man whose personal life devolved into acerbity and alcoholism. A man who moved back in with his mother at 44. A man whose genius dried up. A man whose friends couldn’t save him. A man who never married. A man who died young. I wonder: if you were to map Kerouac’s crisscross-country wanderings, to stretch them four-directionally in both space and time, would it truly be random, “spontaneous?” Or would it trace that same decline from order to disorder, turning and spiraling like that very widening gyre?
And yet there is still beauty there. I still enjoy Kerouac, can still read him and allow myself to be transported into his worlds. But now its a different type of escapism, something more akin to fantasy, a world full of unreal characters, wonder, and myth. I say none of this to quash anyone’s idealism. Dream if you want to. Move to LA. Live on couches. Party hard. Just know that Kerouac’s life was inglorious, and perhaps that is what gets missed by so many in their readings of On the Road: so many have read this as a blueprint, and yet too few understand it as a warning.
But who knows? Maybe in a few years, when I hit my inevitable midlife crisis, I’ll read it again, will re-dip my cup into that fountain of youth and unearth all that unbridled, quixotical hope. I reserve the right to change my mind.
Thanks for reading! Until next time…
