My Approach to Writing, These Days

aka Bob Dylan picks up the electric guitar

The Musicians by Michelangelo Merisi da Caravaggio, 1595

There are seasons to being a writer. The first, a decade ago, was the belief I was no such thing. I mean, is a nihilist who doesn’t publish anything about meaninglessness even a nihilist? And yet: a recurring whisper, seemingly emerging from the depths of nowhere, urged me to gather the courage to share something—anything, really.

Then came the unavoidable, much-bandied season of impostor syndrome. Quite real indeed. But, as it turned out, a small but loud group of individuals liked what I had to say, which led to the season of feeling pretty darn giddy! For nearly two years, I published every Friday. About halfway through that cycle, with everyone asking where all my interest in psychology and dharma came from, it dawned on me that I, as a writer, hadn’t been telling the (full) truth.

Hemingway, another good drunk, once said: write the truest sentence you know. I’ll try that, I thought, and go from there. Beast, Angel, Madman was the debut story of my addiction when I first revealed an overview of what I had been through, the fountainhead from which my dollop of wisdom came. A few essays on addiction later, and some further, crucially supportive praise from strangers on the internet, led to an encore of genuine giddiness.

Again, as if from nowhere, mentor figures, all published authors, emerged around me, cheering me on. They said, dude, you can write, you should give this thing a go—be the real deal, get an agent and a publisher. In my mind, I’d never pursue traditional publishing, because why would I? Substack makes it so easy, and all that sounds like a lot of gamesmanship. (It sounded scary, too.)

I gave it the ol’ college try, and the first stages went far better than anyone hoped: I received offers from several agents, some from prestigious, fancy literary studios. Getting an agent as a new author is, in and of itself, a big deal hardly guaranteed.

Yet getting an agent is just Step 1. A wise friend warned me, be prepared for more rejection. Step 2 is a book deal. At this stage, the notorious slew of rejections that writers experience came surely my way. It stung, but honestly not so bad. In a former life, I trained revenue teams on how to deal with rejection. This was different than that: this was me, and what I was selling was my story and my soul. But I managed to apply a few of the lessons I used to teach to my own life.

What hurt most was the intense striving towards something, trying to adapt myself to a track that feels like it’s already broken or obsolete—that is, traditional publishing paired with internet brain rot. It hurts to feel like I’m dreaming last century’s dream.

This past year, as a writer, I’ve entered part of the season defined by stagnancy. I’ve kept up my prose production rate well enough, but my reading of non-dharma works has fallen precipitously, as has my short-term hopes for publishing a “major work.” I’m putting my focus elsewhere, which has been an enormous gift. And I say that with as little unconscious projection as possible for a guy like me.

When it comes to my own creations, I’m no longer interested in writing only super polished think-pieces meant to exist forever on the shelf. I’ve also become especially weary of writing about addiction, despite it being, for better or worse, my beat. Don’t get me wrong: I still have a handful of essays on addiction and the future of recovery I’m working on. But even Bob Dylan couldn’t help but eventually pick up the electric guitar and try something new, even though he knew his fans would never tire of his singularly acoustic sound. (Indeed, many felt betrayed by his decision.) Audience capture dynamics like this can reciprocally narrow a writer’s focus, and thus perhaps, his enjoyment and impact.

Today I find myself somewhat yearning for the old days of this newsletter—Fridays on the oLo—when I mostly waxed about philosophy, wrote stories, vignettes, a multi-essay series on love, and all sorts of other sundry dopeness. One of the benefits of stepping away from my traditional publishing aspirations, at least for now, is that I no longer give a fuck about appealing to a “sufficiently” broad audience. I cannot hide who I am, a nerdy surfing doofus into dharma and wide-legged sweatpants that don’t choke my ankles with those hateful strips of elastic at the bottom.

The good news is that I’ve learned enough about creative and artistic cycles to know that this phase—feeling bored with what once worked—is not a problem. Far from it. If you can’t tell, lately I’ve been trying to switch things up. Writing shorter essays in the same morning that I publish. Pieces that drop the pretense of being a “professional” or someone who overly romanticizes the sacred without giving proper homage to the deliciously profane. My intention is to write without censoring myself due to fear of rejection. Or without letting the Great Sensitivities of our times haunt my process.

For this same reason, in pursuit of keeping my creative faculties sharp, I’ve been experimenting with making short videos. I like to tinker with new modes of expression and see these as an extension of my writing. I have also learned that it doesn’t really matter which medium I play—whether lengthy essays, videos, men’s groups, or non-profits—I just must be making something. My spirit demands it. The fire needs room to breathe. I already know what happens when I try to smother it. I end up running laps around the Tenderloin, crazy-eyed, ripping cigs like there’s no tomorrow.

What I’m discussing here, in terms of the seasons of artistic creation, isn’t about constantly overworking. Making art, creating anything novel from a place of sincere intention is typically rejuvenating, restful even. That’s how it’s felt for me this year. Perhaps it’s not fair to characterize my current stage as “stagnancy,” despite the lingering sorrow about a dream outgrown. This season has also brought some big changes to my life. It’s arguably the most significant shift I've undergone on a personal level since entering recovery. Undoubtedly, it has been partly fueled by releasing my aspirations of writing a book and ceasing to strive so damn hard—instead, all in favor of exploring what other wonders might emerge from that enigmatic nowhere. I’ll have more to write about this all in the coming months. Or maybe I won’t, because I’m still letting it seep in, and to write about it might only do violence to its immensity.

What I do know is, I feel extremely free right now, as an artistic creator and a human on this earth. For that I feel very lucky, and I hope maybe sometimes I do or say something that you read or hear that will make you feel a little bit of that too. I’m finally gearing up to start the Deep Fix podcast, but this time for real. Like, I actually have music and interviews lined up and am doing the damn thing. People tell me I have a soothing voice. But I look forward to you being the judge of that.