To Try or Not To Try? A Writer’s Dilemma

There’s a quote from the writer Charles Bukowski. Lots of people dislike Bukowski for lots of different reasons, but that’s okay, because tonight we’re just considering one quote from him without context:
It comes from one of his final works, a slim volume with the wonderfully prolix title of “The Captain is Out to Lunch and the Sailors Have Taken Over the Ship.”
In the book, he reassesses several writers who had a great influence on him when he was younger: Ernest Hemingway, Carson McCullers, Sherwood Anderson.
Anderson, with his deceptively simple style, seemed to have aged the best, while Hemingway with his lean and much more striking simplicity suffered greatly upon reassessment. “Hemingway tried too hard,” Bukowski claimed. “You could feel the hard work in his writing.”
Naturally some would consider criticizing someone for trying their hardest to be an unfair and maybe even ridiculous line of attack. Aren’t you supposed to try, do what you can, summon as much light as you can against the gathering and inevitable darkness? We know we’re fallible and weak and mortal and that both we and our works will eventually perish from this Earth. But to succumb to that realization prematurely, to surrender and not even try, isn’t that tantamount to sin, even for the areligious? “Do not go gently into that good night,” Dylan Thomas urges in his wonderful villanelle of the same name. “Be angry at the sun,” poet Robinson Jeffers likewise counsels. Clearly, being angry at the sun is not going to make the sun budge an inch or cool off a single degree, but that’s sort of the point. Humans are uniquely conscious (probably) and this consciousness can either work as a paralyzing hindrance or a great motivating engine. You either fight or succumb, so why not fight as long as you can as hard as you can?
Hemingway used to call stepping to the blank page “facing the white bull,” and facing down an angry bull is not the kind of thing one can do in a half-assed way.
What, though, is the alternative to trying too hard? Not trying at all? Someone committed to such a worldview would never bother writing anything in the first place, or at least writing anything more than some chicken scratch on a cocktail napkin at happy hour. I suppose one could sit lax before their typewriter, crack their knuckles, shrug their shoulders, and just let it all flow out.
There are certainly writers who had this kind of freewheeling approach to the craft. Think of Jack Kerouac’s improvisational, jazz-inspired staccato punching of the keys of his Underwood. I’ve never seen footage of him typing, only still photos of him hunkered over the machine and brooding, with a lit cigarette dangling from his sulking lips. I imagine, though, that if he were viewed in video or in person we would see him tapping his leg like a drummer working the kick while his fingers strayed o’er the keys like Gene Krupa doing rimshots.
It's certainly the feel invoked by On the Road, which was produced on one long and interrupted typewritten scroll, and reads like it.
Bukowski hated Kerouac’s writing, which is a little ironic, considering his own aesthetic philosophy—at least as it applies to work rate—isn’t much different than Kerouac’s. He wrote his first novel, “Post Office,” in roughly two weeks; it’s a ragged and uneven work, but undeniably entertaining.
So far as I know Truman Capote never publicly opined on Charles Bukowski, and likely wouldn’t have had anything good to say about him or his writing, anyway. He did, however, give his assessment of On the Road, opining, “That’s not writing, that’s typing.” His point, it seems, is that the unmediated nature of the writing, the lack of deliberation and consideration (as if crafting words were making moves in chess) ruined the work. Kerouac had failed to try hard enough, at least in Capote’s estimation.
Maybe then, there’s some kind of golden mean, a synthesis between the thesis of hard work and the antithesis of basically automatic writing, treating a keyboard like an Ouija planchette.
This debate—to try or just let it happen—is hardly confined to the world of the writer.
The boxer Oscar De La Hoya, like many pugilists, became obsessed with golf at some point in his career. Initially he did it just to relax, as a hobby to distract him from the serious work of making men bleed. Eventually, though, he discovered that this seemingly innocuous hobby was altering his view of boxing. He claimed golf taught him not to push so hard, not to try or to force it in the ring.
That when he attempted to bash the ball, it usually shanked, or he even whiffed, and that there was a corollary “trying too hard” in the ring that was best avoided.
“Don’t force the knockout,” the old heads say to the young impetuous pugilists. “Trust the process and the knockout will come.” “Stay loose and only clench the fist directly before impact on the opponent’s body or face.”
De La Hoya had no doubt heard all this before, but didn’t really process it until he got onto the green. Probably until it came time to stop driving and start putting, a part of the game where trying too hard can quickly take you from birdie to bogey.
Ultimately, every writer must decide for themselves how hard to try, or how light or heavy a touch to give it. And since we are talking about an art and not a science here, there is probably no right answer. Not only that, but a writer who tries very hard at one point might adopt the lighter touch later in their career. One might even change tact from paragraph to paragraph, the same way a scalpel is better suited to some tasks while a chainsaw gets the job done better with other work.
For me, the main effort does not come when I’m actually writing, engaging with the word as I’m doing right now. It is fighting through the free-floating fear, the anxiety and paralysis that come from procrastinating, thinking about writing rather than doing it. Walking around my house, letting the thoughts of imposter syndrome crowd out my ideas, letting fear curdle into self-loathing. Letting my insecurities basically gnaw away at my creative impulse until the writing muscle goes slack and my fear of failure becomes a self-fulfilling prophecy. And I fail before I even get a chance to try, hard or otherwise.
Once seated, the battle is nine-tenths won or lost, but at least it has been joined.
Or, to paraphrase Stanely Kubrick quoting fellow cinema titan Steven Spielberg: “The hardest part of directing a film is getting out of the car.”
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Published on September 04, 2025 12:32 Tags: aesthetics, bukowski, capote, kerouac, trying, writing
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