In other news, there’s a certain custom I observe almost every October (or November, give or take), and though I was busy writing a book at this time, while also pursuing other philosophical endeavors, I saw no reason why this year should be different. Thus, I passed this most recent October leisurely rereading Jack Kerouac’s On the Road.
Something happens to me every time I read this book. All kinds of intense longings and sharp aches for something better start “oozing” out of my “existential holes” (whatever those are) and begin to flood my being. I start feeling the urge to buy some old jalopy from the 1930s and use it journey out West so that I can revisit the majesty of that region and let it continue its transforming work inside my otherwise beaten soul. I begin to think in terms of simplicity and minimalism. I start feeling a connection to the roads and streets and bricks of old buildings. I begin thinking about smoking cigarettes (which I hate) and drinking my coffee pitch black and rolling the sleeves of my white T-shirt up so that my (unimpressive) biceps show. I begin to think that perhaps I should grease my hair back and wear a faded blazer and walk around with an old typewriter.
And my aspirations as a writer are always aroused when I re-read On the Road. I’m haunted by this short book, which I find to be more forthright than descriptive, more calming than exhilarating, and an impressive execution of understatement—that is, saying so much while saying so little. And then I recall that this book was influential enough to capture and define an entire generation, that when it came out in 1957, it embodied the essence and attitude of America at that time. Was Kerouac just lucky that he wrote the right book at the right time, or was it all perfectly orchestrated? He died young, so I’ll never get to ask him. If I could, I might also ask how in the hell he got this thing published when it’s quite probably the worst execution of grammar in all literature. I mean, this book is the exact opposite of everything they teach in writing class. Here we have a literary giant, a truly defining work that’s thought by many to be one of the best books of modern times, yet it’s a masterful example of grammatical rule-breaking. Here, I think, is empirical proof that the rules only exist for those who do not write. We who do write are allowed to move past those rules and decide for ourselves what needs to be said and how it needs to be said… because that’s our prerogative.
Reading even one passage of On the Road makes me feel I might be wasting my life, that I’ve squandered all my opportunities to do something great and meaningful and important, that I’ve allowed the bullshit nothingness of everyday trifles to rob me of my ability to simply enjoy the subtle wonder of just being alive and breathing.
Taken from my book, Letters From a Dissident Philosopher