michael-dean-k/

A summary is maybe 1% of the original, but notably it loses all of the source—this is what defines the flat blurb, the just-in-time factoid. A functional interpretation.

A compression is different in that it can only draw from the source. I’m finding that 40-70% compressions reduce length but increase information density.

What would a 1% compression look like? In a 10,000 word essay, which 100 words might contain the smallest fractal of the whole, both in terms of substance and style? This doesn’t amount to selecting your favorite paragraph, but finding your favorite 5-10 sentences from across a piece, and stitching them together, so that the kernel of the idea, the thing that’s likely to remain after the brutal compression of memory, is right there in front of you.

For every essay I read, what if I required myself to make that 1% compression? What if I returned to that list often, quickly refreshing the way a piece moved me. Would I actually remember them over time? Would I actually enact those lessons and change my life?

I wonder if there’s both an expansion and compression arc that’s required to fully get something: XS>S>M>L>XL>L>M>S>XS. You start small to even build intrigue to enter a text (ie: a recommendation from a friend); maybe you read smaller compressions, and gradually build up to the XL full version, with all the footnotes, annotations, and liner notes. But then there’s an equally necessary process of unwinding, of distilling and compressing what you uniquely take away from something—perhaps an aphorism; a souvenir on your shelf that is lodging into your working memory each morning.

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.

V7. Analog editing is pretty fun. There’s something helpful in seeing your older frozen version beneath the new thing emerging. I do this a lot in Miro, but feels different on paper. Can’t quite articulate why yet, other than the ease/freedom of drawing. Just feels like there’s value in moving up and down the writing tech stack (voice, handwriting, typewriter, computer, AI). 

After this whole analog ordeal, I distilled my essay into a new question, and then ran it through a new vibe-coded essay interrogation app I made, before it one-shot generated v8, which sucked (as a whole), but also unknotted a lot of the big v7s issues. So next step is to make a digital outline for v9, where I’ll meticulously look through all the notes and scraps and refile the good parts into an new outline, and then maybe typewrite the final version in one huff. 

I think the point I’m arriving at is that every medium has its strengths and weaknesses, and it helps to shift around to get the power of each, until you find a version of the idea that feels right. (Of course, this is very inefficient and slow, potentially endless, but probably worth it for the few ideas you care about most, and so that’s why I’m trying to be more rapid with notes like this, so I’m less rushed on the whale essays.)

This helps clarify my stance on AI writing too, that it can be helpful for sketches that advance or challenge your thinking, but it should probably never be the last link in the process, because the essay you share should be the best articulation of your own thoughts in your own words. Typically AI is framed as a shortcut for slopjockeys (which is fair because that’s how it’s commonly used—I mean my wife and I just had to file a warranty claim for our broken stroller, and it’s not worth wasting prose on that), but if it extends your thinking, and points you to new regions of pondering when you shower or drive, which then inspires original ideas, is that cheating?

Recently found a book on my grandfather’s bookshelf by William Zinser (author of On Writing) from the 1980s on word processors. Apparently he started as a technophobe, but after actually buying an IBM and moving up the stack, he found it to be a pleasure that augmented his methods and habits from earlier mediums. I think the unique paranoia of AI is that it can easily replace and cheapen your whole process if you let it, but that’s your choice, independent of anyone else.

I've always thought 'writing shows you what you think and editing helps you change your mind'—and maybe that’s a decent heuristic—but it’s more complicated than that. I think it’s possible for writing to do the opposite of what we hope, to lead to self-deception. A few thoughts on how:

1. Premature convergence: When you start drafting, you unlock a new stream of thoughts, but once you find a new center of gravity (a potential thesis), it’s common for all further thoughts to reinforce the thing you happened to stumble on, regardless of its substance. Beyond a point, writing can ossify & lock you into a frame.

2. Aesthetic attachment: Once you’re trying to make a ‘good’ essay around your thesis, it’s easy to become enamored by phrases, sentences, images, and sources. Expression (vibes/voice) is an entirely different thing than thinking. You can dress up a static/wrong thought to be beautiful/persuasive.

3. The sunk cost fallacy: after you spend hours on an essay and share it, it’s likely that you’ll continue to believe it. If you’re wrong, you’ll have ‘wasted’ that time. If you change your mind, your readers will have an outdated model of you (OFC, views evolve over time, but I wonder if publishing leads to short-term friction in your evolution).

One possible way around this is to, as soon as you think you found your thesis, to rigorously consider and explore the antithesis (not as a rhetorical strawman, but to really, earnestly, consider the opposite). It means a given draft will be scatter-brained and contradictory, but it’s how you find a synthesis, a more refined thesis. And once you find that, you start over, and repeat, until you end up somewhere that is far more nuanced, interesting, and weird than where you started.

The thing I’m grasping at is that thinking & expression are often at odds, and before you commit to an idea worth expressing, you need to go through rounds of unglamorous self-interrogation. There is probably a mode where thinking _is_expression, but the risk is not wanting to shed something that is elegantly said. One way through this it to get meta and explicitly express your doubt and your evolving POV; I think this is what separates essays from articles and propaganda, and it stops you from brainwashing yourself.

The debate around the essay comes down to whether you see it as (1) an anarchist vibe where form, order, patterns, legibility, and even basic conventions of usage don't matter—it's an act of rebellion, a release valve, a social spark, etc.—or, (2) as a work of literature that deserves 50-100 hours of your time, multiple drafts, OCD/perfectionism, and writerly pain that translates to readerly smoothness. We don't need to have 2 camps here. We can have both.

IMO, default mode should be rapid, unhinged, nearly schizophrenic rants, that have little restraint. Of those, maybe 1 in 10 should be slightly edited. And then of those, maybe 1 in 10 should be highly edited. ~3 unhinged rants per day ~= 1 polished essay per month. There's a natural filter. If you're a generative thinker, you have far more ideas than you can ever render coherently, so it makes sense to only polish a small portion.

Venkatesh Rao is an inspiration, and I suspect he has some mammoth ideas hiding behind sloppy Substack posts. As a reader of his, half the time I come across axis-shifting ideas, and the other half I'm frustrated at how his lack of polish adds so much friction to get it. His post today seems like a dig at polished writers without any intellectual substance. That definitely exists, but it's not either/or. I wish VR would take the craft of writing more seriously (sometimes) so more people could understand how he thinks, which could maybe help the writerly types think better. But if you tell weak thinkers to write faster, you don't surface more gems in dumpsters, you get more dumpsters of shit.

What are the types of telling? (in show vs. tell):

1. Telling is compression; instead of showing us a specific moment of when you were alone in the woods at the night, you compact the story and say “I'm scared of the woods.” In compression, you lose the details that help us get why (the weird sounds, the dead trees, etc.). It is oversimplified to insist that you should show every idea in lucid detail. It's too much to take on. You want to compress the inessential to create a hierarchy, so that the essential details are given space in proportion to their importance.

2. Telling lets you connect the dots and find patterns: “the definition of terror comes from X, and this relates to Y, and so it means Z.” If you want to come up with principles, you have to abstract things down to compact, vague placeholders; it’s the only way we can hold multiple things in our mind at once to see the relationships between them. The problem, when writers only exist in this word of abstraction, it’s dense and boring.

The trick isn’t to pick one mode or the other (show vs. tell), but to master how you blend between them. It means you can actually write about X 2-3 times, even in a single paragraph. ie: first you locate X (tell), then you show X in extreme detail and emotional power (show), then you connect X to related nodes Y & Z (tell). This is a tell-show-tell sandwich, with 75% showing. It gives you both depth (by showing) and width (by telling).

This means any piece of material you have is fractal. You have to be able to zoom in to find specific examples, and zoom out to find principles and patterns. A writer/editor needs to always be bridging between abstract and concrete; if someone gives a principle, they’ll say “give me an example,” and if someone gives a story, they’ll say “what is the larger principle?”

Garret on numeracy:

I suggest spelling out either: (1) all numbers below 10 or; (2) all numbers below 20 or (3) all numbers below 100 with the exception of your chapter references. If there are too many numbers like this in your pose, then the important numbers won’t stand out as much, like the reference examples later in this paragraph. Garner prefers option 1. DFW prefers option 2. Chicago style is option 3.

My reply:

Given different writers have their own range, is there a case for “all numbers below 2”? I’d argue that anything that is a quantity, other than a/one, can justify being a numeral: 1) it creates a visual fabric, where all quantity gets a specific symbol, and 2) it’s create the least readerly friction (I look to reduce this where I can because in other areas I intentionally add friction for specific ideas/phrases. To spell out “seventy-six,” in my mind, is a poor use of someone’s mental resources, an unnecessary drain of stamina. Even “7” over “seven” saves a few milliseconds of stamina that I will expend elsewhere. Also I love numbers. I’m really a math guy, and all my prose is just really filler between my numbers.

Here are some idiosyncratic rules on how to make these decisions:

1. If two numbers occur in a sentence or a paragraph, use numbers so the reader can effortlessly see and compare quantities in a pre-read scan.
2. If you have a set of labeled or numbered items to make a framework (a, b, c) or (1, 2, 3), you can default to spelling out a number so it doesn’t appear to be part of the framework.
3. By intentionally spelling out large numbers, you make a point (“we waited for one hundred and twelve seconds for the waiter to return”). The delay of processing numbers can be used for effect.

This is a good example of rebelling against prescriptive, absolute rules: “everything under 10 must be spelt out.”

Behind any technical skills, there are more general skills that enable those technical skills to develop in the first place. For example, underneath any of my writing/editing ability is patience, focus, and endurance. I’m realizing that some people are capped at 3-4 hours of focused work per day, and the norm is to spend something like 4-6 hours on feeds, YouTube, or Netflix. If you’re able to get into 10-12 hour flows each day, and spend considerable time on your projects, you’re compressing a year’s worth of growth into a month.

Essay Architecture should expand your conception of what an essay can be.

As long as it’s profitable enough to sustain itself, I have the opportunity think differently on the product management front. I can subtly defy “the customer is always right” rule. Each writer has their own goals around writing. Maybe they only want to write personal essays, or academic essays, or memos, or whatever. Part of my vision could be for this app to gradually open your mind to what an essay can be.

The scoring system can and should be confrontational. A flaw of GPT-4o is that it’s sycophantic; it’s so attuned to you that it’s a mirror, reflecting back your strengths but also concealing your blindspots. If I do this right, an objective quality standard will reveal your blindspots instead of hide them.

The purpose of asking “what’s your goal?” on upload isn’t so that all the feedback warps to match your goal; it helps me challenge you (“I know you’re going for X, but why does that preclude you from also achieving Y?”).

Comment on Silvio's essay:

This was great but the 4/2 entry could use a bit of editing. Kidding. Love this, and also, as you would expect, I disagree. I hope to respond to this sooner or later in detail (and it might even be fun to do some public letters back and forth).

This reminds me of Kerouac’s story; he was disgusted by the idea of editing, and remained unknown for years. On the Road was illegible, until Malcolm Crowley edited it 5 years later. By making it legible, he achieved international fame, and it ended up destroying him. There is a cost and risk of legibility, but that’s a different story I think.

“Editing is violence” is a powerful phrase, and speaks to the strength/disorientation of having your ideas/mind/self rewired. It’s something like an ego death. I personally think it’s valuable which is why I invite people to be as violent as they want with feedback (meaning, Im willing to start again from scratch if you can convince me, but I won’t just agree with anything you say so you’ll like it — I think there’s a stance to be open but extremely skeptical with all external feedback).

I think there a near-spiritual meta-ability in the learning how to detach from mental forms and be open to experience something with truly fresh eyes. Sometime this comes from within, but often it comes from time, weed, or, an editor.

I do agree with you that there’s a petty type of editing where you’re trying to appease a narrow/fleeting market need, but ultimately I think it’s up to the writer to hold their own internal vision for an idea when it makes exposure to a crowd. Maybe it’s not about total isolation/artistry and not about total market conformity/desperation, but as Emerson says, the sweetness of solitude among the madness of crowd.

I just wonder if it’s possible to honor both states: most expression deserves to be untouched, but some ideas are worth treating as a puzzle that you invite your friends to help you solve.

Just read several hundred Kanye tweets. I wonder if you take all his tweets since Feb 6 / the Super Bowl, and take the time to meticulously arrange them like a developmental editor would, might it make sense? If you cut 25%, removed the ALL CAPS, and made a prose essay out of re-arranged Kanye tweets, might there be a semi-coherent perspective that’s not completely insane?

On conceptual vs. syntactical ambiguity: it’s okay or a concept to have multiple interpretations (that’s adds layers of meaning), but rarely do you want your syntax to be ambiguous (not sure of what the writer means because of clumsy syntax). The best case is: “I know what you mean, but I’m temporarily unsure of the implications.”

I asked AI to read 4 years of posts from the Write of Passage Circle community and make some inferences about me. “Please make elaborate and nuanced observations about the writer in this writing community. This includes most of their posts over 4 years:”

[Thought about writing journey and evolution for 4 seconds]

Then I asked it to review and summarize all of my feedback:

“This person’s feedback style is comprehensive, encouraging, and highly attuned to the writer’s goals and potential blind spots. They typically begin by reading a piece in full, noting both the high-level structure and the sentence-level details, then they leave a warm yet direct set of in-line comments and an overarching summary at the end. On a technical level, they pay attention to flow (pointing out where transitions feel jarring), the rhythm and length of sentences (citing tools like Hemingway to reduce complexity), and the integrity of the introduction and conclusion (urging the writer to hook the reader early and tie loose threads later). They have a particular knack for spotting an essay’s “shiny dime”—the focal insight or big question—and suggesting ways to make that thread more explicit. More personally, they encourage writers to dig deeper into their experiences and vulnerabilities, often recommending they add or expand on anecdotes that bring a concept to life. Emotionally, they aim to both reassure and push the writer; they highlight what’s working well so the author feels confident, while showing them how certain passages might confuse or overwhelm readers. On a psychological level, they aren’t afraid to address hesitations or anxieties about publishing, reminding people that the aim is personal expression and growth, not robotic perfection. Their feedback also has a subtle empathetic dimension: even as they recommend major cuts, restructuring paragraphs, or clarifying language, they do so by linking those decisions back to the writer’s intent, audience expectations, and the unique voice that should shine through. They encourage the writer to remain playful, observant, and personal (the POP framework), and to see revision less as “fixing mistakes” and more as a creative opportunity to clarify the core idea. Across their many comments—whether they’re dissecting a tricky hook, advising a friendlier tone, or praising a bold personal story—they balance methodical critique with genuine enthusiasm, prompting writers to embrace edits as part of discovering the essay’s essence and pushing it to the next level.”

The word “diary” implies a space of personal recollection and non-judgment. There is no right or wrong. It has one job, it’s a mirror. Now Rubin says:

“Everything we make can be [a diary], a personal reflection of who we are, in that moment of time. It doesn’t have to be the greatest you can ever do. It doesn’t have to have any expectation that it can change the world. It doesn’t have to sell a certain number of copies for any reason. It doesn’t have any of things. All it has is: I’m making this thing for me, and I want to do it to the best of my ability, to where I feel good about it, and it’s honest, honest of where I’m at.”

Is editing dishonest?

I resonate the idea with purging the chorus of false reasons (greatness, impact, sales) … but if you want to do something “to the best of your ability,” does that not imply the recursive act of looking at your work and judging it? I actually think self-criticism is one of the hardest and most honest things you can do.

Judgment is a profound force. It shouldn’t be your primary lens to reality, but it is an indispensable razor into the truth, and it’s something we ought to be grateful for: our whole society is built on it.

ChatGPT now offers an “editing” service that is really the illusion of editing. Like a Google Doc, it will highlight string of text, and leave comments in the margins. You can even click “implement all changes.” At an interface level, this is absolutely editing. But read the final version. It’s offering sentence-level line edits without a real sense of what the resultant whole is.