Existential crises and why writing is a trip

Not so long ago I found myself in a Slack conversation with a friend who’s begun to do more writing lately. “Writing is hard,” we both agreed. I was a capital-W “Writer” for a long time. Though it’s been a few years since that was true, I too have been leaning more toward some form of that pursuit again, and I found myself sharing some thoughts in Slack that—in part because I’m excessively fond of quoting myself—I thought I’d share (and expand on) here as well.

Writing is a trip. I didn’t study writing (or much of anything else, for that matter) in college. Instead, I taught myself to write the kind of journalism I wanted to write by reverse engineering New Yorker stories. I would take a story paragraph by paragraph, count every word in each by hand, and then assign a function to each chunk of text. Intro, colorful detail, nut graf, personal aside, ambiguous conclusion, kicker, etc., etc. Eventually, I’d done that on enough stories (not that many, actually) that I could understand a rough structure I thought they followed, and could use that structure to guide the architecture of my own submissions.

I lived in New York at the time, and a friend was kind enough to introduce me to an editor of The New Yorker’s Talk of the Town column. I pitched Talk stories for months on end, without success. I pitched that editor until he left that job, then pitched the next Talk editor. All I ever got were kind rejections, the kind where the editor tells you that your story isn’t right for the magazine at this time, but they’d welcome seeing more from you at a future date.

I took those editors at their word and just kept pitching. I have no idea how many stories I had pitched (a dozen?), but finally, at long last, three editors in, I got a bite, on a story about a New York club kid who may or may not have been the basis for a Bret Easton Ellis character. It wasn’t really the kind of story closest to my heart, but it sold to The New Yorker, was published in The New Yorker (I have sold stories to them that weren’t published), and became the foundation for many of the pitches I’d write for years to come (“I’ve written for The New Yorker, among other publications…”).


That story was more or less the beginning of my freelance career, but what’s notable about it is that I had to do a whole lot of writing to get there. And this is the one thing I’ve found is true throughout everything I’ve written (and in work in other contexts as well): You have to turn out a lot of shit alongside the gleaming diamonds that are the pieces of work you’re proud of. For every brilliant (or even decent) paragraph you produce as a writer, you probably also write ten crap ones, which will never see the light of day. (I have no idea what the actual ratio is, but it feels about like that, or possibly worse.)

And I don’t find that ratio has changed all that much over the history of me as a writer. Perhaps the diamonds have gotten sparklier (when I’m in form), but I still have to shovel a whole bunch of shit alongside them, just to get to material that’s halfway good.

This, possibly more than anything else, is the most difficult thing about being a writer: You have to be willing to create a lot more bad material than good material, without losing hope along the way.

Writers talk about this all the time, but the fact is that you have to shovel a volume of shit that essentially produces an existential crisis every time you sit down to consider your production. In order to find those nuggets of gold, you have to sift through all the dirt and detritus, and you have to be the one that calls bullshit on your own attempts to sell yourself a pile of iron pyrite. (You see how fraught this is already?) You can’t be a good writer without also being mercilessly self-critical. And that’s on top of the unending stream of rejection you’ll receive if you’re pitching editors and/or agents on any kind of meaningful schedule. And even while all that’s going on you have to muster some really heroic discernment and tenacity in order to make the gut check that lets you hold on to the good stuff. It’s a buffeting gale of internal conflict and it’s all too much for almost anyone I’ve met.

Of course, that doesn’t stop us. By any rational measure, the odds are against you. But most new ventures of any kind are destined for failure—which means that if you played the odds, you’d never start anything. That’s not the game. The game is believing you’ve found a way—whether through talent, expertise, skill, or plain hard work (and all are valid approaches)—to turn the odds in your favor.


And if you’re trying to write about yourself, especially if you’re addressing difficult subjects (as the friend I mentioned is doing), the trip is even tougher. And if you’re trying to write honestly about yourself—well, that’s a whole journey in itself.

One of my favorite notions is what I call the impossibility of autobiography. This is the idea that—no matter how hard you try, no matter how earnest your intent or how detached your ego mind—you just can’t actually tell the truth about yourself, despite whatever intellectual or emotional contortions you might employ. It just isn’t possible.

This is more a corollary of the truth than it is a function of your skill as a writer. The truth is not what happened. (What happened is what happened.) The truth is how you express what happened. It’s merely the output that results from feeding an event into the description machine in your mind, a machine whose inner workings change from day to day, sometimes from hour to hour. Programmatically, truth = description(event). What actually happened (the event) is little more than a parameter that’s passed into the description method, which returns an object of type truth.

While the event doesn’t change, the description can be totally different, from one person to the next, from one moment to the next, from one mood to the next, from one sentence to the next, or even from phrase to phrase or word to word. What we call the “truth” is really nothing more than the impression we get from viewing events through whatever lens we happen to be using at the time. As writers, we put that impression down on paper or the screen (and then the reader filters it through their own lens, of course), but it’s only ever an impression. Objective reality is not really something we get to deal in.

The impossibility of autobiography means that whatever truth you tell is only the truth of that moment, the truth of that context. You can never objectively transmit some foundational, Platonic sense of what happened or who you are, because the act of transmission itself colors the message. You can’t use the #nofilter tag in your personal history; you have to start with Willow or Valencia and make your choices and adjustments from there.

Don’t believe me? Take five minutes and write a few sentences objectively describing your 17-year-old self. Now compare those with the journals you kept at the time (or whatever other artifacts you have access to, even if only in memory). Pretty much the same, right? Ah. I didn’t think so.


Where does that leave us? If we can never tell the “truth” about ourselves, is there even value in attempting? Just what are we sharing when we share an episode of personal history? Did I really reverse engineer all those New Yorker stories or not?

I really did, but the significance of that episode is only partly to do with the work I did to become a Writer. Just as important is the fact that I chose that episode to illustrate that work. I could have described 14-year-old me cold-calling farmers in California’s Central Valley to “investigate” a headline I’d spotted in a local paper during a family trip. (About what, I can’t recall. I was sure it was scandalous, though.) I could have narrated the two years before the mast I spent at Reuters, complete with the day I tanked a couple of stocks by posting a (very) stale headline, and experienced so much mortification that the bureau chief declined to call me out on the carpet after taking one look at my face. Hell, I could have made something up.

I could have done all those things, but those would have been different truths, different autobiographies. The naively analytical work I did, was that the most important episode in the story of my becoming a writer? Maybe. Did I really analyze more than a single New Yorker piece? To tell you the truth (see what I did there?), I’m not sure. I don’t know if I know anymore. Does it even matter? What’s “true” is that it’s the episode that’s most important to me today, the one I felt, at the moment of writing, would convey my message in the most effective way I could. And maybe that’s the point: When we write about our past, we’re never writing about the person we were—we’re always writing about the person we are today. What we’re saying, even when we talk about events long gone, is as much about who we are right now as it is about who we were then.

And this is why the existential crises are so important, why we can’t produce great work without them. Because writing is never entirely about the subject of the piece, and always very much about who the writer is right now. The soul searching that is necessary to do good writing, especially to do good autobiographical writing, is only partly about understanding how to say what you want to say; it’s also about understanding who’s saying it, about why you want to say that thing, about looking in at yourself and exposing what you find. You can’t just look back at events or at a subject and “tell the truth” about them; in the process, you’re also telling the reader about your self, about your thoughts and opinions and prejudices and views. In the end, honest writing means that it’s you that you’re putting on display, even as you pretend to hold something else up for examination. Try making that gut check for hours every day.

As a writer, it’s you that you’re judging as you delete that sentence you loved so much an hour before. It’s you that you’re rejecting when you ditch your opening paragraph and sit staring at a blank screen for long, dull minutes while you wait for your next temporarily-great idea to come to you. It’s you you’re offering to a public full of strangers who couldn’t possibly care as much about you as you do yourself. But it’s also you you’re celebrating, just in the act of sending something out there to an editor, an audience, or even a friend. It’s you that you’re becoming, through the crucible of trying to do the kind of work you want to do.

Writing is hard, it’s true. It’s a trip. It takes courage, foolhardiness, an appetite for punishment, and an iron gut. You’ll fail at it nine times out of ten. And if that’s your average, chances are you’re doing it right.