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.

“The Internet needs a quality algorithm.” This was the opening line of my essay prize announcement, and I want to revisit it now that it's done. Is there a correlation between writing quality and audience size? 

Algorithms are low-trust right now because they’re adversarial—“for you” gaslighting (usually)—and they reward engagement, popularity, monetization, etc. The 2010s-era algorithms are based on discrete events: clicks, likes, measurable things. They might look at keywords to guess the topic of an essay, but it’s effectively blind to the overall quality of a piece. Quality is nebulous, after all. Small magazines can each have their own vision of what’s good, but for a million/billion-person network, there’s no consensus, and quantity is way more important anyway.

So this essay competition was a v1 attempt to define and search for quality. The overall search space was small, but it was a chance to experiment with curation, and resulted in The Best Internet Essays 2025. It’s interesting to me that the featured writers ended up varying in audience size, evenly distributed between 10s, to 100s, to 1,000s, to 10,000+ subscribers.

Again, limited sample, but interesting to ponder: the tangible thing (reach) is a power law distribution (1% have big audiences), but the intangible thing (quality), the thing that matters more, is independent of scale. It means that for all the great writers with 10k audiences who are highly visible, there are possibly 100x writers of similar caliber who are undiscovered, in algorithmic obscurity. 

This isn’t too surprising, and the usual reply is, “well it’s not enough to write well, it’s your responsibility to be consistent, to be your own marketer and publicist, to make sure your work gets read.” I get that this is what’s been required, but what if it weren’t? Wouldn’t it be better if a platform could search for quality at scale so writers could just do their thing? This would also give visibility to those who aren't full-time writers, people who publish 1-2 essays per year around the interesting problems they’re working on, but have no bandwidth to build an audience each week.

Still have to think through v2, the 2026 prize, but the question in my mind is how can I expand the search space? Can I have agents scan the Internet, assemble RSS feeds to find great essays, design an algorithm to filter for the previously intangible, build community into the process, and then curate/share the stuff that comes through? The aspiration is to get better each year at surfacing great essays from independent writers on the basis of merit, and this book is what came through the first pass.