michael-dean-k/

I published 38 "essays" in June, averaging at ~600 words, totaling at ~22,800 words (that's a pretty good month for me; I usually go between 10-30k). That same overall output could also be spliced up as four long form essays at 5,700 words each. The question here, can you count these small things as essays?

If you look at Montaigne, and especially Bacon, they each had some shorter one around 500 words. I have other contemporary essay book that feature writings that are exclusively 2-3 pages each. So historically, yes, there's a case for short non-fiction musings to be called "essays," but is it really about shortness?

It's more about formality and effort. In recent years, I was set on writing "unitive essays," ones that integrated all the known patterns, ones that went through many rounds of editing, ones that would be timeless. I still, of course, value that and aspire to it; I'm just currently in a phase where time is more burst-like. Such is life with a 5-month-old daughter. Deep flow states are hard to come by, and so instead, I'm logging little ideas all day, and whenever I get to the computer, with the mental space to write, the goal is to pick one idea and articulate it fully. Can I write and publish this idea, here and now?

It's an approach void of editing, which feels right for right now. I've thought so analytically about the craft, and the goal now is to see if I can weave in patterns on the fly. This doesn't mean I can successfully scope and prose every idea to a 5/5 on a single go. Most ideas—including probably this one—are started pre-maturely, and have limits on what they can become without scrapping it all and restarting from a new frame. Of course, the point is for ideas to mature through writing, but a great thesis can be so cognitively reorienting to nullify a draft's whole premise. But maybes that's the thing to build towards?

I didn't have this idea before I started this essay, but maybe an essay should contain an earnest shock, something in the moment that negates, inverts, and breaks the structural logic above. Wouldn't there be a thrill in witnessing a live epiphany, and then watching the writer clarify how everything previously covered may be true/false in light of the revelation?

You may have noticed, every paragraph so far has ended with a question. I suppose I'm playing with this idea to start with a clear question, and then continuously drive forward until a spontaneous question triggers something new, and I can fold back into that original question with an answer from a different dimension, a side door I never knew existed. An essay is less about the length; whether it's 300 or 30,000 words, it's more so about the value of what's discovered.

I was looking at my archive earlier, at everything I published in the last year. There are 363 "essays" (most of which are expanded logs), averaging at 370 words each. Of those I have about 22 essays flagged as "favorites," meaning, they've elevated to a special section, and earned the formality of cover art. This means that only 6% of the ideas I write in a given year are worth carrying forward. With time, that will probably atrophy even further. Even 1% of output per year is high: if you can write 3.6 timeless essays per year, that's prolific. DFW, if you look at what was anthologized over his career, only put out 1-2 per year. One approach to this is to pick be very selective, only chiseling a hand few of ideas; the other is hyper-publishing, trusting that curiosity will bring you to unexpected places, and the emergent "winners" are not ones you could ever predict. What makes something a winner?

It must be a fusion of things; again, quality is the transcendence of categories. This gets into what-makes-something-the-best-essay territory. The originality and nature of the subject itself matters, which is part of why I like the idea of reading and writing wider. But the essays I like most are the ones that also fuse in most or all of the compositional patterns around that thesis. There's only one I wrote in the last year that comes close. Maybe all of them have some personal experience peppered in, but the best ones, I feel, are ones where the writer is deeply immersed in a place, and all the things about them become allegorical. So you can read and write, quick or slow, short or long, but what you make is shaped by how you live, which is why it might be worth capturing your daily thoughts in prose.

1. As a writer needs a site of one's own, a place designed for their particular psychology so they can be the most prolific, honest, adventurous version of themselves. Solitude is important. Montaigne, the founder of the essay, wrote up in his tower for a decade. When you are your own audience, your practice is self-justifying. You are intrinsically fulfilled, and do it regardless of validation, growth, or revenue. To become self-validating is to become a nuclear engine of creativity. When you write on your own site, chances are you will spend much time on ideas that no one will read. That's inefficient, but essays are inefficient. I need to ruthlessly follow what matters to me, with no fear of being illegible or invisible to others.
2. That said, you can and should invite others into your garage. I still plan to keep my Substack and post there, but it will be more like a newsletter, a digest of the controlled explosions happening in my own neighborhood. I do believe in the value, even, the responsibility, of writing in public. By making your place tidy enough for friends, strangers, students, customers, mentors, heroes, whoever, to come in, it makes you put an extra oomph in your crafting of language, and it creates seeds from which relationships can grow. When you have visitors in your territory, they play by your own rules, so you're generally safe from mobs and barbarians. They will not trample over your furniture and throw the books from your shelf like they would in the town square.
3. In 2023, I was hopeful that Substack could be an all-in-one platform—a website/newsletter/discovery engine—but it has heavily shifted into an app-centric social media platform. The app starts you off in an endless, algorithmic, engagement-ranked feed, and the design has slowly evolved to trap you in the app. When you click in article, the default URL is the Substack one. When you click into a person, you can't even go to their site anymore; you can only view them through their profile template. This means all the customization and self-archiving and mythologizing that goes into your site is off limits to the app, the thing they're trying to corrall attention through.
4. I'm very allergic to "Substack is dead" posts, and most of the critique is often a projection of their own weaknesses (ie: when people naturally stop growing, it's easy to blame the algorithm than to take responsibility for it). In my case, the Substack algorithm has worked pretty well over the last two years, and I'd be stupid to abandon it. But the whole system has limited my intrinsic passion to write, and that matters more, enough that I'm willing to take the risk with a split publishing system: Substack newsletters that link out to my site.
5. Back in 2020, a Write of Passage concept was the "public to private bridge," meaning you find people in social media feeds, but then redirect them back to a place of your own. Now that Substack is mostly a social media network, I think that same strategy applies. It's not where I want to host my essays anymore. I'll host newsletters and paid content there, but the timeless stuff wants to live in a place that is timeless.
6. If you have a portfolio of writing, Substack feels like a pretty bad way to make your old work legible, especially within the app. There are no tags or sections. No about page. No navigation system. No ability to frame call to actions as visually dominant. The beauty of your website, especially if you build it from local markdown files, is (1) you have a single source of truth for all your writing, and (2) you can just respawn new interface and navigation systems as your portfolio evolves.
7. Even though Substack lets you export your essays, it's really more like a failsafe, a backup incase you ever decide to leave. Of course, it's very nice to have that! But it's still a cloud-based system, where editing your past files is slow and clunky, and you have limited ability to point your essays elsewhere. When I have a local folder of my essays, I can very easily spin up a stylized website around any essay, or any group of essays (say, for example, if I'm making a proposal and I want to curate a handful of essays. I can point my AI at any combination of files and folders for context.

This essay tapped into a striking definition of timelessness. He doesn’t get there until halfway through though, and I found myself disagreeing with—or at least, questioning—a lot of his earlier points (I’ll come back to this). The main point is distilled into this: the best essays are “ineffective” because they reveal the timeless problems that each generation fails to synthesize. Timeless essays speak to the common foils in the human operating system: the blindspots of parents, the lies of institutions, the avoidance of mortality, the ineffability of relationships, the mundanities that are never captured in enough detail. These are different than “discovery” essays, like Darwin’s Origin of Species. The holy grail of an essay is surprise, and a timeless essay is not just sueprising for one generation, it’s surprising for every generation. And so timelessness, then, is a type of “breadth of applicability.”

PG also ventures into a familiar territory of “essay as a mode of thinking.” Where as in the past he used “the river” as his metaphor (2004), this time it’s a tree. You start from an origin, and then you explore many different branches in search of generality x novelty. What is a good starting question? He says a good one is “outrageous, counterintuitive, overambitious, and heterodox.” It doesn’t have to be a complete thesis, but some puzzling gap, and importantly something you care about. You won’t be able to stretch an origin question into cascading insight unless you have a unique angle into it. The origin doesn’t matter too much though, because it’s a recursive process, and you can eventually get to the best question in “a few hops.” I love how he emphasizes that you need to write to explore branches of a tree, and there are many dead ends; you realize how you are mistaken, incomplete, and inelegant (you go from vague to bad). Don’t get discouraged by these; finding your false assumptions is possibly the only way to really begin.

Despite loving his whole exploration of “mode,” I don’t think that means you have to neglect essay as “genre”; he says form/style don’t matter in “the best essay,” and I disagree, obviously. He has Darwin as the pinnacle example of an essay, and I’m really challenged by that (I definitely have to read it now). Is that an essay or a scientific paper, just captured in shortform non-fiction? He seems to imply that the essay is at its best a vehicle for discovery, as a mechanism to bring forth surprising, important, and useful ideas. From the creator of “make things people want,” this isn’t surprising. Even though a new theory of evolution had broad implications for society, I assume the paper itself is technical, intended for a scientific niche audience, which in my mind, makes it more like a scientific paper than an essay. An essay is something that is universal/general enough for the average person to read. An essay, I think, functions like an information transfer system between specialized facets of society; it’s about making your specific niche legible to all the other niches, and I don’t think that was the specific goal of Darwin's writing (even though it was inevitably understood by everyone, it wasn’t through the writing, but from the effects of the writing).

(Added: Another note on Graham’s notion of best as timelessness: he says that timeless esasys are the perennial insights that each generation can’t absob. This implies that the insight is never enough: even if you know something, there is often a lack of wisdom in applying it to your own circumstance. And so really, these unteachable lessons are ones that can only be obtained through personal experience. Does this point to the fact that all essays need to be personal? Maybe bland insights can’t be digested by a reader, but if they are integrated to vivid personal experience, experience vicariously, then might this actually be the best medium to transfer wisdom?)

So there is an ESSAY (the “unitive essay,” a term maybe I’ll run with), and then there are sub-genres of essays: the personal essay, the lyrical essay, the fragmented essay, the braided essay, the trickster essay (you can just make up whatever adjective you want). All these sub-genres work in a local context. But I think the ESSAY is worth it because it’s timeless and universal. I say this because each reader, in our times, and in future times, has their own blinders, their own subset of patterns that they care about. When you write for a niche or a subgenre audience, you’re appealing to a fixed group with specific blinders. But when you do the hard thing of trying to synthesize all 27 patterns, you have something that is likely to appeal to anyone, regardless of their blinders. A well-rounded essay can make someone care about any topic. And, a unitive essay also expands the lens of the reader (“oh damn I never knew an essay could have this and that”). Also, and finally, the Internet is a context scrambler. Your URL is dislodged from any stream, any entry point, and anyone can arrive from anywhere at any time, and so the unitive essay is the thing most likely to resonate with any particular stranger who stumbles into your living room.

Robert Atwan (founding editor of Best American Essays) said that the timely is for articles and the timeless is for essays. That’s helpful, but I think it’s most powerful when you fuse the two, when you use something timely to capture a timeless theme. Also, when I go back and read old writers, I find it neat when I learn specific historical details of their time, and so it’s helpful to think that rendering 2025 in high detail would actually be appreciated by a theoretical reader in the 2100s. You have a unique opportunity to show your circumstance at a level of detail that no other generation will, and so I think it’s wrong to dismiss the timely.