One Year on Substack, An Attempt
Reflections on Year 1
There is a story that is widely known in some academic circles that goes something like this–two years before his 40th birthday in 1571, a French nobleman named Michel de Montaigne retired to his family’s castle to write. More specifically, he retired to the library of his castle, which was a tower where, surrounded by books, he withdrew from family and social life and spent 10 years writing his book “Essais.”
History still knows of Montaigne’s self-seclusion because the book he birthed during his decade in the tower merged autobiography, research, literary and spiritual reflection, and the mundane activities of domestic life into a new hybrid form that today we call “the essay.” It will be my contention in this post that the essay is among our most noble literary forms, but that much of what are called “essays” today degrade the form.
The essay genre in its highest form will show you its structure as you create it. It will move like a symphony, or maybe a Jackson Pollock painting. You will not know until far along the composition process what you are even writing about. At some point in revision, disparate parts may find harmony, adjacent sections may move together, the need for connecting tissue may be revealed, and most often that original idea you sat down to capture will fade entirely. At the end of writing an essay, the writer will step back and realize that what they’ve written could not have been planned ahead of time, that essay writing allows the author to find a form born from circling a subject, exploring the tangents, and allowing an organic vision to be born. You will attempt to say one thing but say another entirely and this is the beauty of the form. It’s something that LLMs cannot, yet, do.
I started writing this Substack one year ago this month because I had a couple of motivations at the time. The first motivation was that in the run-up to the 2024 Presidential election I was shockingly inspired and without knowing what it was I wanted to say I gave myself the assignment to write an entry a week about the election. I found myself, for the first time in my life, siding with the right wing party in the United States–a position that, as someone who championed Bernie Sanders in the classroom and even gave my students bonus points if they attended an Occupy Wall Street gathering in 2011, was as surprising to me as it would turn out to be to those who knew me. I never expected to lose so many friends for following my curiosity and exploring my shifting opinions and beliefs, but as Vonnegut said “and so it goes.” By asking myself the “how did I get here” question, my thinking broadened in multiple ways, I began to piece together a more formal worldview, and the essay form came back to me.
My second motivation for starting down the Endless American Road without a clear destination in mind, was that I had spent years stymied as a writer. In life, I find that whenever the feeling that others call depression comes creeping up the answer for me is always to plan some time in nature with my dogs far from the bustling city lights as quickly as possible. Similarly, I figure that by getting moving here I might free myself of what some call “Writer’s Block,” but is not. There is only the attempt, ever, and you either do it or you don’t.
I am proud of the work I’ve done here over the past year if for no reason other than that I have done it. After so many years of being frozen in place, I have written and self-published 16 pieces over the last year and that feels boast-worthy. The length and quality of this work varies, but that it is mine, in my voice, circling my reflections and obsessions is true.
Despite many years of being an early tech adopter, I am now finding that the pace of innovation online is outpacing me and it’s not because I can’t see or understand the evolution, it’s simply that I do not care. I am tired of X posts, TikToks, and irrational clickbait Facebook posts. I am tired of trying to fit into the Feed–a place where opinions must be biting, sardonic, and rage or fear inducing, where all information is meant to be consumed quickly and forgotten—a place where scenes of war and videos of dogs doing silly things sit side-by-side. The Essay has a hard time competing for attention in such a world, but nothing on social media has ever moved me as much as Annie Dillard’s “Total Eclipse”.
Yet, all I want to do is to write essays and novels, to navigate the vast complexity of what it means to be human in a world that is moving so quickly, and I’ve wasted too much time already. Maybe, as so many messages tell me, there is no place for independent-minded white men in the literary landscape today. With reading among all age groups falling off a cliff and the elites asserting monolithic ideological control over what is published, what is prized, and what is promoted, I would feel truly futile if I didn’t love the process of writing itself.
Yet, as I was reviewing the 16 pieces I have written this year and began to reflect on the year behind me and envision what I can see for the year ahead, something emerged that I wasn’t expecting.
The second piece of writing I published here was a reflection on the loss of my dog Maxwell. I didn’t know when I published it that a few months later I would lose my first dog, Daphne, as well. Of those 16 pieces published here four of them were written about these two dogs. I began to realize that in writing about the loss of my dogs, so much more was coming up–the changes in myself, the magic that holds my world together, the sense of adventure that gives my life color. In my dogs, I found the world again, and in writing about losing them I found my way, slowly, over the course of a year, back to the essay form.
Looking at the four pieces about my dogs I had the sense that something larger was emerging from them, but how they fit together was not clear. So, I did what every college student today would do; I fed it all into Grok with very specific instructions to re-arrange the form without altering the writing. The LLM version allowed me to see a blueprint for how to move ahead. I printed that version along with the original version and with scissors and tape put together an essay. Many drafts later, I am sitting on a finished, polished essay that needs one more revision before I send it out for publication. What strikes me about this experiment is that I realize that the key to writing an essay, for me, is just to write–a lot. To write as well as I can, to keep turning a stone over until I have said all that I have to say, then to put all the pieces together, ruthlessly cut and paste, and turn and turn until something original emerges. This is the essence of an essay.
The final product, “One of the Pack”, is the first complete piece of long form writing that I have finished in years and it feels really, really good to have finished it.
So, in the year ahead, I will keep writing here in short form. I will follow the muse wherever it takes me, and offline I will work to see how all of this fits together. My goal is to write in longer forms, with discipline, curiosity, and purpose. I will try to send things out for publication because I need this audience to grow, and I will see if there is any hunger in the market for the musings of a middle aged white guy, but regardless of whether or not the market accepts me, I will write.
I will write because my dogs inspired me to, because it’s all I’ve ever wanted to do, because I have to believe that in this era of disposable information and short attention spans there will one day come a return to meaning, to longer forms. I envision a generation so turned off and bored by AI and social media that they pick up books again and start reading (the raw dogging plane trend gives me hope, though what a waste of time when one could be reading!). When that generation emerges, I hope to have plenty to offer them as an elder of the pre-internet world.
And if this doesn’t happen, I’ll be happier knowing that I cancelled Netflix and turned off Youtube. That I sat down with my second generation of dogs napping at my feet, and tried to make sense of the world as I see it.
I don’t have a castle and can’t afford to withdraw from the world, but in the time that I have I will create. That, anyway, will be my attempt.
Thank you for coming down the road with me. There’s a lot to see out here!
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