On the Kerouacian Lifestyle

At 18, I read On the Road. Like so many before, Kerouac’s novel instantly inspired me. The frenetic cross-country travel, the wild friends, the wilder adventures, and Kerouac’s bottomless passion were powerfully attractive forces to a young man raised in suburbia. I soon devoured Kerouac’s second most popular novel, The Dharma Bums, which I found even more endearing as it spurred a long-time interest in Buddhism and deepened my (already deep) love for the mountains.

After college—like so many before—I tried on the Kerouacian lifestyle. I owned little, moved often, and made friends everywhere. I structured my life around the pursuit of freedom, adventure, novelty,  personal connections, and creative accomplishment.

For most who attempt it, this lifestyle is fun for a few years, and then it becomes exhausting. It gets in the way of larger goals that offer meaning and security, like having a home, a stable relationship, a stable job, and a consistent friend group. It’s hard to sustain financially. And of course, it requires a certain amount of luck and privilege; if you’re raising a child or caring for a sick family member, you won’t be zipping around the country for very long.

Yet somehow, my twenties passed, and I never gave this lifestyle up. Instead, I doubled down. Creating Unschool Adventures wove travel into my means of subsistence. Working at Not Back to School Camp and Deer Crossing Camp gave me friends to visit all over the country (and the world). Furnished sublets and Airbnb rooms provided temporary home bases; camping and Couchsurfing filled the nooks and crannies. My family members were always happy for me to visit (the trick: don’t stay longer than a week). Writing books lent me a sense of purpose wherever I found myself, and my incipient public speaking career rewarded migration.

I did stay put a few times, prompted by a romantic relationship. I moved to Asheville, North Carolina, for love. I moved to Boulder, Colorado, for infatuation. I moved to Germany for love. I rented a 1-bedroom cabin in South Lake Tahoe, California, for two long summers in 2015 and 2016 (initially for the sake of a relationship, but eventually for my love of the land). But the Kerouacian lifestyle fought hard, and eventually won, each of these battles. The rooted life couldn’t compete with the joys and possibilities of constant motion. Having figured out many parts of the practicality equation—money, friends, meaning—I struggled to convince myself that life would be better in one place.

The year 2019 marks 18 full years of my infatuation with Kerouac’s ideas and lifestyle. Unwittingly propelled by temporal symmetry, I picked up one of Kerouac’s biographies last month to see how much his life actually reflected his words. Long story short, Kerouac did live the Kerouacian lifestyle—at least until his mid-thirties when he found financial success and his life starting going down the tubes.

I found interesting parallels between Kerouac’s life and my own. As a young man, he was impulsive and flighty. He joined the Navy, but then “one afternoon when he’d had enough field drill, Kerouac put down his gun and walked off to peaceful solitude in the base library.” I pulled similar stunts in my first outdoor education jobs. He made grand plans and then ditched them to hang with Allen Ginsburg and other college buddies, much as I did with my aborted thru-hike of the Pacific Crest Trail and my endless visits to my friends Matt and Patrick.

At age 27 Kerouac received his first book contract, a modest sum but enough to get him by; this was roughly the same age that I found my initial success with writing and trip-leading. (I imagine that without such a milestone in one’s twenties, it’s difficult to lead a Kerouacian lifestyle without feeling like you’re going nowhere career-wise.) He mostly avoided working for anyone else, preferring to cobble together a frugal life bouncing between friends, family, and short-term accommodations. That’s me, without a doubt. (Although I don’t mooch off my mother, like Kerouac constantly did.)

Kerouac married twice, briefly. “One of the reasons that he left his first wife Edie,” biographer Ann Charters wrote, “was that life with her would have been too comfortable.” Stability and comfort also unnerve me, an impulse that doesn’t pair well with traditional relationships. He was a highly social person who also craved solitude (even though real solitude quickly bored and unnerved him), another pairing that feels intimately familiar.

The last decade of Kerouac’s life was sad and sometimes shameful. He married a third time (to a woman who essentially served as his infirm mother’s caretaker), frittered away his wealth, alienated most of his friends, and died an alcoholic at age 47.

How much of Kerouac’s decline was due to his lifestyle? Perhaps this was the secret question I was asking myself throughout the biography. Reflecting on Kerouac’s downward spiral at age 37 (in the Big Sur era), the biographer Ann Charters writes:

The road had come full circle. Kerouac’s bleak vision of himself turned back to his last sight of Cassady at the end of On The Road, beaten and defeated, drifting from one end of the country to the other with no real attachment to life or to love, the end of the dream of life as an adventure with nothing but good times ahead.

There are many reasons why Kerouac lost control of his life—fame and alcohol seem most prominent—but in this analysis I still see a warning: the Kerouacian lifestyle, lived without temperance, can lead you to toward a beaten, defeated, and lonely existence. Those who take On the Road too literally are signing up for a very narrow vision of freedom: “a return to a solipsistic world of childhood,” as Charters writes, “to an irresponsibility so complete that no other world could ever intrude for long.”

Irresponsibility and self-centeredness: those are the true enemies. To the extent that the Kerouacian lifestyle enables those demons, it is clearly unsustainable. But if one can overcome those demons, then I see no reason that such a lifestyle must end, even it looks different as one gets older.

Four years ago, I sat down and thought hard about what it means to live nowhere. In the end, I decided that the lifestyle was still right for me. Today, I still believe that. So I press on.

See you somewhere down the road.


Published December 10th, 2019



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