In my recent DFW phase (anyone in a David Foster Wallace phase calls him DFW), I came across his 1992 essay, How Tracy Austin Broke My Heart. It’s a microcosmic masterpiece. He dissects Austin’s “Beyond Center Court,” and through this one memoir he sheds light on why the whole genre is a disappointment. Not only that, the essay is absolutely loaded with showing (not telling)–another Charlie-ism. I have her voice in my head saying, “don’t tell us your thoughts, feelings, or emotions, just show us.”

I immediately thought of her, but decided not to send it. The first time I mentioned DFW in casual conversation with Charlie, she followed up with a link-loaded email, and geez, I was oblivious to the Lynchian extremes he went to in his relationship harassment. But weeks later, her husband read that same Tracy Austin essay and insisted she read it. Now Charlie connects with David exclusively over their shared loathing of celebrity memoirs (visual of furious underlining, throwing books, and venting).

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After some back and forth, we decided to do a collaborative review of a review.

First, check out Charlie’s latest post and her podcast where she breaks down why this essay shines as an example of showing (for example, the first page features 8 back-to-back quotes with no explanations). 

I started my analysis by identifying and classifying each example; after impulsively counting them, it came out to a suspiciously perfect number: 100. There were 67 examples referencing Beyond Center Count, 41 of which were direct quotes. There were 30 other references unrelated to Tracy Austin (including other sports, Kant, the definition of “inspire,” etc.). Finally, there were 3 personal stories from DFW’s personal life mixed in: we see in a bookstore embarrassingly buying this memoir, we see him as an envious 18-year-old watching Austin on TV, and we see his self-consciousness intrude on his own tennis matches.

Assuming this essay is 5,000 words, that’s a density of 2 examples per every 100 words.

But aside from the sheer volume of showing, the main lesson for me (which I break down in my video) is how he has an insane “example rhythm.” Not all examples are equal; it could be a word, a phrase, a sentence, or a multi-paragraph story. Similar to how writers avoid back-to-back sentences of the same length to make their writing rhythmic, DFW is constantly weaving between small, medium, and large examples.

As exemplary as this essay is for the art of showing, I was shocked to learn that 45% of the essay still consists of the forbidden telling. Honestly, I think telling gets a bad rep. Yes, showing is the visual half of writing that immerses your reader in a hallucinatory trance, but telling has its purposes too. It frames what you show, and it helps transition from scene to scene. 

I created an outline that strips this DFW essay of all it’s showing so that you can see its skeleton (I’ve been finding it helpful to frame outlines as Q&A pairs). The bolded text below (his answers) are what he’s telling us, and each point is backed up with 10+ examples. The showing is the proof to support what he’s telling us. Telling without showing leads to flimsy and boring arguments. But telling someone a specific sequence of things with lucid visual proof is something like a psychedelic (def: mind-changing) experience.

Outline:

1. Why do we yearn for sports memoirs to be great?

   1. Why was DFW disappointed? (it’s filled with cliches)

   2. Why do we crave sports memoirs? (we envy quantifiable and televisable genius)

2. Why was Tracy Austin’s memoir so bad?

   1. Where did the ghost writer mess up? (the prose, the audience, the structure)

   2. Why was Tracy so naive? (child stars are ignorant to realities around excellence)

   3. How could the memoir have been good? (it was a classic Greek tragedy)

   4. What is so shockingly bad about it? (despite her crazy story, the words were pulseless)

3. Why might all sports memoirs be bad?

   1. Where else do you find cliche language in sports? (post-game interviews)

   2. What might be going on?(his thesis: gifted athletes are so in-the-zone that they can't process or articulate what’s happening to them)

Here’s a video called Structural Telling, Rhythmic Showing. It breaks down how he builds his structure around telling, but then ultimately grips and convinces us through different types of showing. 

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Let’s riff:

• What are your favorite or least favorite parts about reading David Foster Wallace?

• Anything to add on showing vs. telling? What works for you?

• After my first draft of this, I saw the new Pope Francis memoir in an airport bookstore. A Google search told me that “Pope Francis is out to prove he’s just a regular guy” and it’s even narrated by Stephen Colbert. This feels like a solid choice to break my memoir virginity?

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I spent 10,000 hours in a design cult. The architecture students were secluded in the woods on the edge of campus, designing small buildings that would never exist (like the one in Zoolander). Refining our drawings and models pushed us to our limits: creatively, psychologically, and physically. One time after not sleeping for 72 hours, I was in a white room surrounded by white models and started hallucinating a technicolor jungle. I couldn’t drive home; my mom had to come pick me up. Obviously it was unsustainable, but it changed my life: it’s where I met my wife and forged my mind.

Architecture school was an intense, 5-year ordeal that instilled in me a reverence for craft. It's a mindset that often feels out of place in the world of online publishing. The Internet is so shaped by marketing, journalism, and entrepreneurship, that it threatens the sensitive ecology needed to make great work. Today’s creators worship speed, attention, data, and growth.

If you're an emerging online writer, maybe you feel stuck on a quality plateau. 

Maybe you're:

• Rushed to publish as often as possible and don’t see yourself improving.

• Stretched too thin to edit or re-write your first draft.

• Frustrated by the challenge of structuring complex ideas.

• Overwhelmed by a heap of scattered writing advice and lack a unifying framework.

• Unaware of how to practice using exercises.

• Isolated from others who care deeply about the craft.

• Tired of the robots, hucksters, and slang-parrots.

I've seen how "studio culture" can put anyone on a continuous arc of improvement. "Studio" refers not just to the physical place, but the curriculum that turns beginners into experts, and the cadences of feedback and publishing. "Culture" refers to everything that emerges from this structure: the shared norms, language, skills, frameworks, rituals, passion, and friendships.

My lens to essay writing—a paradoxical medium that both died in 9th grade English class, while also being the most important skill in the 21st century—is shaped by architecture. I’m an interdisciplinary thinker, a visual diagrammer, and a fuser of analysis and creativity. In the last 3 years, I’ve designed the curriculum for Write of Passage, founded the editor program, and have given feedback on over a thousand essays.

If you join me you'll:

• See the invisible patterns behind great essays.

• Find others with a shared reverence for craft.

• Write the best essays you've ever written.

There are 3 different ways you can start crafting essays like an architect:

1_ Do you want visualized writing theory in your inbox?

For $10/month (or $100/year), you'll have access to Essay Architecture. Over the year I'll be deconstructing classic essays and synthesizing my insights into a curriculum. My goal is to absorb all the writing advice scattered across websites and libraries, unifying everything that matters into a single mega-structure. This stream of posts will put you on an arc of continuous improvement. You’ll upgrade your ability to scope ideas, structure essays, and write with voice.

Get Essay Architecture

2_ Are you a practicing writer looking to join a studio and get quality feedback?

Note: This turned into Essay Club in October 2024.

The Writer's Studio is a network of craft-focused writers. It's the most immediate and tangible way to upgrade what you publish. You'll have access to a Calendly to book live 1:1 feedback, whenever you need it, either with me or someone in the Studio. This structure encourages you to iterate, to test your revisions across different readers, and to confirm that your ideas resonate. Never ship a blind paragraph.

This is the “Founding Member” tier on Substack (offered at $300/year). You’ll have access to the posts from Essay Architecture (above), but this is where you put theory into practice. You’ll meet other writers and work together on your creative problems, just like we did in architecture school.

Join the Writer's Studio

3_ Do you need a coach to visually guide you through your biggest creative project?

The key thing that separates architecture school from a traditional college major (I started in finance) is the apprentice-like structure. I met with a professor, 1:1, twice a week, for years. After showing them my progress, they would react, give feedback, and guide me on my next steps. They would scope out what to study, what to keep in mind, and what to deliver by our next meeting. 

In Dean's Office, I'll use Miro to help you through an essay, project, course, launch, book, or memoir. Over weeks or months, we'll meet regularly on Zoom to brainstorm, scope ideas, diagram concepts, study precedents, reverse outline, restructure, and channel your voice. I’m looking to work closely with ~10 writers in 2024 to shape ideas at the edge of our shared ability. In order to give everything I can to these 1:1 projects, space is limited. The most important thing for me is to work with others who are dedicated to making something timeless.

Apply

“This is one of the best places to learn how to write on the Internet.” – Doz

“Michael’s approach of using visual feedback is like nothing I’ve ever seen before. He was like an architect taking the bricks of ideas I had and gluing them together in a way that makes sense.” – Jen Vermet

“Michael is not ‘the best’ at what he does, he is ‘the only.’ His visuospatial style of outlining what needs to change in an essay and what I might work on in subsequent drafts was a total game changer. He was thorough, generative, and patient. And as a result of our collaboration I now have a pillar piece on my Substack (A Pilgrimage for Book People) that got featured by Substack in Substack Reads and is something I can be proud of for the rest of my writing career.” – Charlie Becker

Let’s riff:

• What does the word “craft” mean to you?

• Any questions on what I’m offering? Reply to this email or leave a comment. There’s no detail too small or philosophical wrench too big.

• I’ll be pinning this page to the nav-bar of my Substack to orient new readers. If I’ve helped you with your writing in any capacity, it would make my day if you write a testimonial that I can share.

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Professor Tootzi was a rude and abrasive genius, an architecture professor so dedicated to his craft—hand drafting 3 hours a day for 50 years on imaginary projects—that he evolved into a snarling creature, one who waddled, talked to himself, cursed in Italian, and rubbed his nipples when thinking. It worked.

His own drawings had a mystic quality, so I decided to trust him. He turned me from a near drop-out to one of the top designers in the school. Hands down, the best teacher I ever had. I learned to find his insults endearing too.

“Shut up, already! Are you an architect or a critic at the New York Times?” Tootzi had zero tolerance for process, explanations, poetry, or bullshit. He wanted to see my drawings and models. Great work speaks for itself. Despite his weirdness, Tootzi instilled in me a philosophy of rationalism: that there are objective criteria behind works of art.

The lessons I learned from him in architecture shaped my thinking around writing. Are there invisible patterns that underlie all great essays?

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Take the time to learn the hidden language_

In architecture school—twice a week—everyone in Tootzi’s studio brought in their little hand-made paper models of fake buildings (which sounds cute, but people would take amphetamines, stay up for 70 hours straight, and brush their teeth in faculty bathrooms, just to make their fake paper buildings as elegant as possible). The social pressure was unreal: it was Judgment Day twice a week.

At the start of each review, Tootzi—without letting anyone defend themselves— arranged everyone’s paper models in a line from best to worst. He was rarely wrong. He felt you should know exactly where you stand in the pack, earning his studio’s nickname, “The Lion’s Den” (in case you haven’t picked up on the cult-like intensity of architecture school, around 300 people enrolled as freshman and only 40 graduated–an 87% dropout rate.) One-by-one, he’d pick up each model, rotate it, commend it, critique it, and finally, attack it with a knife.

I may have been extremely sleep deprived, but Tootzi pulled off design miracles, over and over. He was a doctor, a shaman of spatial proportions. It seemed like he could instantly understand and unfuck the saddest heap of paper that dreamt of being a building. In hindsight, his suggestions were so obvious, as if we were blind to the potential of our own creations.

Eventually it clicked. Tootzi knew a secret visual language of patterns that his students weren’t yet fluent in, including me. I got a copy of Francis Ching’s Form, Space, and Order, a visual textbook on the fundamentals of spatial design. I kept it in my backpack and read it obsessively.

Regardless of whether a building is classic or modern, secular or religious, a home or a skyscraper, it is governed by the fundamentals of architecture: a proportion of solids and voids, shaped by walls, floors, and columns, organized by function, connected through circulation, symbolically articulated through light, color, rhythm, and texture, anchored in a site and culture, to be occupied by humans, containing psychologies and biologies, both general and specific. These are the rules. You can’t break them, but you can bend them. It’s a big sudoku: an architect has to synthesize a range of overlapping patterns into a single harmonious thing.

Before I knew the fundamentals, architecture school was a struggle. Despite putting in the work and turning nocturnal, I got a C- in my first design fundies class. I was hopeless, ready to drop out and go to a local community college to pursue a career as a jazz drummer. My mother cried. I stuck with it, studied Ching’s book, and was lucky to have a string of world-class professors.

Within a year, I got very good, very fast. Just a year after almost quitting, I won a school-wide design competition as the youngest entrant. I went on to win all 3 competitions during my undergrad years, and also won the thesis award for the 5-year program. But the biggest accomplishment was Tootzi’s reaction at my final review.

Now, my fake building was made out of wood. The master–feared by students, faculty, and even the dean of the program–picked up my model, rotated it around, asked some clarifying questions, put it down, then paused. “I have nothing to add. This project is tectonically perfect.” He spent the next 10 minutes articulating all the patterns at play to the class. 

Editing is easier when you know the patterns_

When it comes to essay writing, the idea of “patterns over process,” is just as relevant.

Tootzi instilled a philosophy of “all that exists is the artifact that’s on the table.” It doesn’t matter if your ideas come from your mind, your heart, your soul, your belly button, the tops of mountains, a bottle of red wine, or from managing an in-house spider colony (this was Salvidore Dali’s process). No matter how you arrive, conscious or unconscious, giddy or trampled, a finished work is imbued with legible patterns that determine how it’s experienced by others.

The patterns speak for themselves. Whatever ends up on the page is self-evident, without context. My college roommate once got roasted by Tootzi for handing out pamphlets before his presentation. “Do you think Rem Koolhas stands outside the Seattle Public Library every morning and hands out pamphlets to persuade you of his brilliance?”

David Foster Wallace had a similar piece of advice for writers: “the reader cannot read your mind.” You don’t get to live in the margins and clarify confusion or expand on your implicit intentions.

Process is extremely important, but more so for the writer than the reader. If your rituals, feelings, and psychology are out of sync, you might not show up to make anything in the first place. It has to be fun. But at a certain point, you need to make the flip and take responsibility for being understood. You write the first draft for yourself, but you write the second draft for a stranger.

So maybe essays always start through some idiosyncratic, non-formulaic, mysterious big-bang, but since readers—by nature of being human— have shared features like curiosity, memory, attention, and linearity, there’s a science in how to make your ideas understandable.

What makes an idea memorable? What makes it believable? How come some titles are catchier than others? How do I hook a reader, orient them, and hold their attention? Why should prose be musical and visual? What are the intangible dimensions of voice? … Are these the right questions? Are there singular answers to all of them? And if so, what would happen if you knew them? Mastered them?

There is a secret architecture behind all great essays, a rational, complex, but finite set of patterns that invisibly operate and affect how our ideas are received. There is a hierarchy of rules that exist and are worth learning. They turn the complexity of essay writing into a set of constraints you can obsess over, master, and eventually, forget. Once you put in the work, the rules become automatic, and bendable; you become so fluent in the science of essays that you can live in the realm of art.

A not boring textbook to visualize essay patterns_

I’ve yet to find the equivalent of Form, Space, and Order for essay writing, so maybe I should write it. Of course, there is an abundance of general writing advice, but I have five gripes with existing writing rules.

• Limiting rules: The grade-school rules of writing neuter creativity. The five-paragraph essay. Templates. No passive voice, no conjunctions and definitely no Oxford commas. These are rigid constraints that narrow your possibilities. Good rules are bendable and expansive.

• Scattered rules: Lots of known writers present great advice as an unstructured list (ie: Umberto Eco’s 36 rules for writing). Each rule might be great, but they’re hard to remember and implement in isolation. I’m inspired by Christopher Alexander’s “A Pattern Language,” where his 253 rules for architecture are broken up into 25 categories. It’s not just one-off tricks. The rules are organized into a comprehensive system for thinking.

• Process rules: Lots of advice for new writers is about how to get started and build a habit. Write every day, make a studio, hone your mindset, organize your notes, be social. There is a huge spectrum that covers everything from cheap motivational porn to sophisticated truths on the psychology of craft. While this advice can be helpful, a textbook on essay craft should be mostly focused on the patterns on the page

• Technical rules: Have you read Elements of Style? Writing about writing tends to be dry, technical, and obsessed with “usage” (the smallest nuances of grammar and syntax). Imagine a textbook that’s not boring. Instead, it’s written with voice, augmented with visuals, and it covers the building blocks of composition that actually matter to modern online writers. Similar to a textbook, it will be sprawling and comprehensive, but so tightly organized that you can easily navigate and zoom in when you want to.

• General rules: Writing advice is often about prose in general, but essays are a specific beast. An essay is different from a diary entry, a newsletter, and a business memo. It is more substantial than a tweet, and less intimidating than a book. Given an essay’s length, you can get feedback, rewrite it, and still publish every week. Done right, an essay is a timeless artifact that uses language to fuse a human with their culture. Out of all the mediums of writing, an essay is perhaps the one most suitable to be a genre-bender. Where is the writing advice that demands the fusion of the soul of a memoirist, the rigor of an academic, and the pen of a poet?

Today I went to the New York Public Library to write out this post and make the sketch below. It’s my attempt to map out what I think are the core patterns behind great essays. It’s structured around 3 core questions (What makes a great idea? How do you give it form? Are you writing with voice?), and then it continuously spirals into deeper sets of triads.

It’s super common for writers to obsess over one part of this map. For example, last summer I spent over 20 hours on a “17 types of repetition Kurt Vonnegut used in Cat’s Cradle,” Twitter thread. Repetition is just one of these 27 patterns, and there are (at least) 17 sub-concepts within it. This map might eventually be a scaffolding that organizes over 500 writing principles, each with multiple examples and rubrics. To start, I want to keep the big picture in mind. I want to make the case that if you’re an essay writer, each of these principles are equally important.

Through 2024, my goal is to write an essay for each of these 27 patterns. I can make the map, but I haven’t internalized every pattern yet. Through writing and talking about these ideas, I imagine it’ll all sync in. It’s not enough to know the secret architecture, it has to be digested, practiced, and etched into your subconscious, until eventually you forget all the rules and devolve back into some refined beast that instantly shapes primal brain putty into its most potent form, making strangers laugh, weep, shiver, make crazy life decisions, and become your friends. 

Read Chapter 1

Let’s talk writing_

Whether we’re friends yet or not, I’d love to connect with you and learn about your relationship with writing essays. I’m bursting with ideas on how to structure, present, and build community around these patterns. I want to create the ultimate essay companion for you, but I want you to tell me what would be most useful. Plus, it’s nice to put faces to email addresses. If you have 30 minutes, let’s do it.

Let's talk writing

I’ve made no effort to get my work read and I’d like to change that soon. I unfortunately have little bandwidth to design Girl-Scout-cookie-grade viral campaigns, so I’ll have to keep it simple. If you’ve been enjoying Dean’s List, scream it from the roof (or, here’s a button).

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Agenda:

• SMALL TALK: I chose to banish the small talk to the footnote feature (weird dreams1, covert art2, Substack chat experiments3). Considering how dense my essays are, I’d like to keep the weekend reading lighter (around 500 words) and more visual.

• DECONSTRUCTED: Last week, I shared a piece called Resurrections On-Demand: Put LSD Back in the Communion Wine. This is probably the craziest idea I’ve ever published. I’ve been carrying this whale for 10 years, and hope to expand on it in the future. In case you didn't catch the essay, here’s a footnote summary.4 Today I'll unpack an idea that was crucial in helping me edit this thing: Saturation.

Saturation

DECONSTRUCTED #3

My first draft of this essay was almost as dry as an academic paper. Sure, I did mention one quick story in the beginning. Personal writing? Check. But then I exploded into a detailed play-by-play of an Ancient Greek odyssey; Michael Dean was nowhere to be found. Midway through the Google Doc, left a refreshing comment:

“Why do you care about this!?”

Of course! I got so bent on ‘unpacking the mysteries,’ that I went on a 1,500 word rage without including even a splash of personal relevance. What happened? I got insecure. Since the thesis is kind of batshit crazy, I obsessed over perfecting the theory’s logic; losing sight of the human element.

So how much personal do I need to weave in? It’s not about volume, but spacing. Sometimes all you need is one sentence to remind your reader you still exist. Sometimes a story is the organizing device of an essay, but in other cases (like this one), you can sprinkle them in.5

By blending stories into ideas, the author has a constant presence. Every 250-400 words, I check back in.

We should avoid one-off globs and focus on weaving the important elements all the way through; whether it’s stories, a voice, or a theme. The essence of a piece should saturate the whole essay.

If you want a theme or tone to be felt by the reader, it needs to be distributed across the essay, from top to bottom. It can’t just exist in one spot; it needs to return at a regular cadence to reinforce itself.

• [ Voice ] comes from [ personality ] saturating the page.

• [ Vulnerability ] comes from [ stories ] saturating the page.

• [ Cohesion ] comes from [ related ideas ] saturating the page.

Whether you want to be more playful, personal, or observational (see: POP Writing), it helps to understand saturation.

How do we pull this off? Highlighters.

Read more

My essay from Wednesday — Margin Matchmaker — went through 17 revisions (with 10 different editors). It sounds excessive for a writer to do this, but it’s a pretty standard method for comedians1 and songwriters. It’s a form of 'social writing.'

The default mode of writing is ‘solo-mode.’ Writers type the keys. Readers swipe the screen. Their communion is async, happening in margins and comments sections. To understand social writing, maybe it’s worth learning from artists that iterate in front of live audiences.

They tweak their material based on reactions from the crowd. They perform the same ideas over and over, to fresh audiences, tweaking it slightly (or radically) each night. Gig to gig, the material gets tighter. Based on the laughter or silence from the night before, the set mutates. Its form, tone, and delivery evolve based on feedback.

Check out this 3-minute video on how a comedian refines the same joke over three sets. At the end, Mike Lawrence says: “The beauty of a place like New York is you can bomb really hard, but you always know the next show is so close.”

Comedians get back-to-back chances to test their material. If they iterate, they’ll discover the best way to deliver an idea. It takes time, but it leads to battle-tested, refined jokes. Best of all, it brings a degree of certainty. They know how their material will land on virgin ears. Only when it can reliably make a crowd roar do they freeze it into permanent recordings.

So how can online writers “road test” their material? We can change feedback from a one-time event to a string of opportunities. I’m still ironing out this process myself, but here are three concepts that are starting to crystallize:

• Flash Feedback — the way to ask for feedback

• Color Maps — the way to implement feedback

• Reader Circuits — the way to test your edits

Flash Feedback

Comedy might be the hardest of the arts. The real-time reaction of the crowd is an sharp reflection of the material. Laughter is an instant, unmistakable, and involuntary signal. This format makes comedy excruciatingly vulnerable, but also rich in feedback.

Feedback is more elusive for online writers. Most people read without engaging. Some like, and fewer reply. Comments are usually a reflection on the whole piece, not the bits. Unlike the comedian, you’re deaf to laughter. There’s no granular feedback at the sentence level. Unless you ask for it, you won’t know how your paragraphs are landing.

Recently, I’ve been asking my editors for “flash feedback.” I basically want micro-reactions — a high frequency of low-resolution comments. I want them to turn off their Editor Brain, and slip into the mind of a “reader in the wild.” Give me gut reactions. Be unapologetic. What is your first impression of this string of letters?

I encourage my editors to give me “binary reactions.” Put simply, is each part ‘good’ or ‘bad’? This can happen in a few ways:

• You can use a (+) or (-) sign.

• You can use simple grunts that indicate (+/-), like “whoa, lol, amazing, interesting, YES” or “confused, meh, boring, lame.”

• You can use emojis 👍.

By making it easy to give flash feedback, you get a higher density of reactions.

I want to know which moments pierce the page. I want to know where I land and where I bomb. Flash feedback not only lets me read the crowd, it lets me know where to edit.

Color Maps

By turning my editor’s reactions into colored-highlights, I get a visual ‘color map’ — it’s a proxy for how my ideas were understood.

Every editor gets a ‘personal copy’ of my master doc. They should be uninfluenced by the reactions of others. If two readers independently highlight “whoa” on a sentence — that’s a great sign. There’s a pattern. It’s likely to trigger a reaction in future readers too.

Once they’re done, I’ll open my ‘master doc’ (in Notion) alongside it. I read through their comments, and highlight the master doc sentences in either green or red.

As I go through multiple rounds, I start to build a dense color map. It’s like a heat map that shows how each sentence is performing. In one glance, I can see where the dopamine wells are, and where the knots are. Instead of guessing where I should start editing, I just follow the colors.

• First I address the reds — anything red is obviously not working. I either rewrite the paragraph, move it, or delete it. It's an obvious area of tension, and should be addressed before any optional tweaking.

• Then I look at the blank spaces — If there were 4 paragraphs of straight slog, what's going on? Could I slay the technical jargon and use a metaphor? I'll examine and compress any dry patches. Each paragraph has to carry its weight — whether it’s an insight, a personal confession, or a splash of humor. If multiple people gloss over a stretch of text, the essay isn’t tight enough. The goal here is density.2

• Finally, I check out the greens — What is working well? If multiple people liked something, then maybe it’s worth drawing extra attention to it. I’ll break these moments into their own paragraph, and sometimes I’ll even bold it and 2x the font size.

Reader Circuits

When we have a draft that’s ready to go, we’ll often share it with everyone who’s up for an exchange. This is the norm in group chats and public forums. You get a chorus of perspectives, incorporate it all, and ship it.

What if it’s actually better to show it to one person at a time?

When you gather all your feedback in a single round, you don’t get to test your edits. There’s an element of guessing. Maybe 3 different readers each point out the same hole in your essay, and offer their own idea on how to fix it. You can pick one, but you won’t know how the revision lands on someone with fresh eyes.

Instead, we should use a “reader circuit” to get feedback.

Instead of sharing 1:many, share in a sequence of back-to-back 1:1s. Start with one person, get feedback, make the edits, and then test those edits on a fresh reader. Repeat as often as you need. By looping this process, and moving through a reader circuit, the draft reaches higher levels of clarity.

This is how comedians do it. They run their new set dozens of times in underground venues before they perform in a high-pressure scenario. They repeat the same joke over and over, across different audiences, until they have certainty. If the idea or delivery isn’t working, they’ll either tweak or cut.

How many loops do you need? It depends. Margin Matchmaker had 17. The 1,000 Day Molt only had 3. If you don’t set a deadline, you can tinker into oblivion. My goal is to fit as many cycles as I can within my interval (whether that’s weekly or monthly).

Eventually, the color map will tell me when to stop editing. When there’s no white-space, and at least one green highlight per paragraph, it’s ready to publish.

These 3 ideas point to the power of social writing. Flash Feedback, Color Maps, and Reader Circuits can’t be done on your own. It all comes down to having a group of honest friends that enjoy wrestling with early-stage ideas. They react, they contribute, and they show you your blindspots. Friends are the secret to delivering ideas at their peak form.

Happy Sunday.

U P D A T E S:

• I published an essay called Margin Matchmaker on Wednesday. Imagine drafting a sentence, and then suddenly an excerpt from your unread library pops into the margins. It’s like a telepathic second brain. This looks into an AI use case for writers outside of the killer chatbot paranoia.3 Today, I’ll deconstruct the process on how I wrote this.

• It’s been a week of racquet sports. It started with virtual reality ping pong,4 and ended with two games of racquetball.5 If you’ve never heard of it, racquetball was the pickleball craze of the 1970s. It’s like indoor tennis fused with handball and pinball — angular, fast, half-court, and 360 degrees. I joined a competitive league where I’m half the age of the next youngest player. I rarely win, but got my first W yesterday.6

• Greek Orthodox Lent started a week ago. I haven’t done the fast in 8 years, but there’s a few reasons why I’m giving it a shot.7 It’s inspiring me to write and publish some of my long-held ideas around Christianity. They’re unorthodox, borderline heretical, but well-intentioned. Next Wednesday, I’ll publish an essay called “Resurrections On-Demand.” It’s about how Christian rituals evolved from an Ancient Greek ceremony that used psychedelics.

L O G S:

I recently learned how to use anchor links in Substack (every header has one). By clicking on a link below, it shoots you into an exact point in my February logs. Instead of copying logs into these Saturday updates, I’ll give you a link menu (single source of truth FTW).

• My mantras for lent

• Why AI makes quality important

• 3 writing lessons from screenwriting

• The prodigal return of natural language

• If Mr. Beast were a writer..

• Why water is 680x more toxic than marijuana

• Chat GPT reverse engineered my writing voice

• Links to the “Fuck You Press” archive (1962)

• The Dusting Rituals of Walter McKenzie

• Rules for a good wi-fi password

• On starting a 1st-person vlog

• Hearing music in your head

Let’s riff:

• What are the pros/cons of your current feedback process? Are you considering any of the ideas from today’s Deconstructed issue?

• How did the menu of logs work? Should I link out to the source log, or copy a few into the issue instead?

• Permission to go on random tangents about racquet sports, virtual reality, religion, and AI.

Leave a comment

Footnotes:

Hey again. My latest molt comes with a fresh publishing cadence too. This is a twice-a-week affair now. On Wednesdays I send essays; they’re evergreen ideas, properly tortured through editing razors. Saturday mornings are casual, and two things happen here:

First, I’ll share some quick updates. But then, for my fellow wordslingers, I’ll reverse engineer my latest essay. Today I’ll do a visual breakdown of the 5 lessons I learned from, “The 1,000 Day Molt: How to Make Decisions Like an Insect.” This feels like an honest (and personally useful) way to write about writing.1

But first, some updates.

Updates:

• ALL MY THOUGHTS. The logs are moving to Substack! If you’ve never seen my logs, check them out here. Since December 2021, I’ve been uploading my notes-to-self onto my website. I write them in prose, so I get the dual benefit of remembering and practicing writing. I archive these each month, and recently learned how to set up a secondary “nav bar” on Substack using “home page links.” Feels like the web circa 2006. Check it out here. Little by little, I’ll migrate the old log archive over.

• ONE WEEK IN 60 SECONDS. 2023 feels like the future. I chat with AI, my coffee mug heats itself2, and my glasses have cameras in them that record my memories. The hardware is made by Rayban, and the software is made by the devil3. Given my roots in VR, I was a willing guinea pig for this experiment. I’ll eventually explain how this all works, but for now, I want to know your reactions with no context. Here’s a video showing clips from the last 7 days, all recorded through my glasses.

Deconstructed:

This idea started as a note on a train, 7 days before I published it. I talked it out with 3 people, and wrote my first draft last Saturday; around 1,400 mediocre words in a 30-minute blitz. It underwent some restructuring and editing the next few mornings. I experimented with a few things on this one: inline footnotes, two-column writing, and editing out loud.

Dean's List

The 1,000 Day Molt

The last few weeks have been a rare hibernation for me. I fell out of my good habits and fell into old addictions. The shadow took over, my imagination dried, and I became distant with the world. Like a little homunculus sitting on a couch in the back of my skull, I looked out the windows of my eyes, operating my limbs through mechanical levers…

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3 years ago · 22 likes · 8 comments · Michael Dean

Here are the 5 takeaways from the process.

1. Reverse outline.

I usually aim to knock out a first draft in a rapid single-take4, so that I can “reverse outline” it. The next day, I compress every paragraph down to a simple title. It gives me an outline of what’s already on the page. By reducing 1,400 words down to 18 little “bits,” I can grasp the whole essay at once. It makes reconstructive surgery easy. I’ll shuffle text blocks into the revised outline, and then rewrite each paragraph.5

2. Editing is re-writing 93%.

The red text was deleted from my first draft, and the green text was added in the final draft. Those little spaces in between show what survived the edit (barely anything). Only 7% of words and phrases made it through. Given the final draft is 93% new, it shows me that my editing is about rewriting. A rewrite doesn’t always have to mean restarting from a blank page (though often it does). In this case, it’s about using a frozen blurt as a jump-off point. Thought is way easier to sculpt and refine when it’s externalized.6

3. Capture tangents in footnotes.

I wanted to test Substack’s new ‘inline footnotes’ feature. When you hover over a footnote in a desktop browser, it pops up over your mouse. No more scrolling down. I found this to be more than a nifty trick. It unlocks something in the creative process, and it’s kind of a paradox. It helped me both cut ruthlessly and add without restraint. My logical mind was empowered to cut anything that botched the linear flow of the piece. But also, my creative mind had permission to explode into divergent tangents, knowing they would find a home in a footnote. In the end, I published 1,018 words of footnotes, or 45% of the length of the essay.

4. Write with two columns.

I’ve been writing in Notion again the last few weeks. Composing in a two column layout is an unlock for editing. It lets you whip text left and right easily, and hide chunks of text within toggles. In a single-column vertical doc, there’s friction to cut and paste down to the bottom. It can take 5-10 seconds, which sounds innocent, but repeated over and over, can break your flow. I find it hard to use my editing sledgehammers in Google Docs. A two-column view lets me see both the canvas and the palette at the same time.

5. Edit with your tongue.

When the essay was done, I read it out loud one paragraph at a time. It was slow, and took over an hour. I’d loop a sentence over and over until I found a better way to say it, and then I’d put that on the page. When you edit with your tongue, you’re more likely to find rhymes, alliterations, and synonyms. Words shed their syllables, and mouthy sentences turn to butter.

Let’s riff:

• Of the 5 points above, which ones landed with you? Are you going to try any of these? What can I clarify?

• Feel free to comment with a link to something you wrote recently, along with a note on the process.

• What are your reactions to the 1st-person video footage? I’m going to write an essay on this soon, so I want a pulse check on your first impressions.

Footnotes:

Jack Kerouac was a famous writer from 1950's, but he referred to his own practice as "sketching." Like a painter, he'd look around slowly to soak in and reflect on the details. As images and memories bubbled up, he'd scribble them into flowery, never-ending sentences.

When Kerouac writes, it feels like he has a direct vein into the subconscious, for better or worse. I admire his ability to access "the source," but he hated editing. A natural result of automatic writing is unpolished noise. His critics have said, "That's not writing, that's typing."

But, if you're patient, among the noise are holy, unbelievable sentences. I make a point to save these. This one is from Dharma Bums. Most of his books are "auto-fiction," meaning the characters and plots closely match his life experience. After three days of poetry readings, Buddhist rituals, and orgies in San Francisco, he heads north to a National Park and writes this on a hike:

"The woods do that to you, they always look familiar, long lost, like the face of a long-dead relative, like an old dream, like a piece of forgotten song drifting across the water, most of all like golden eternities of past childhood or past manhood and all the living and the dying and the heartbreak that went on a million years ago and the clouds as they pass overhead seem to testify (by their own lonesome familiarity) to this feeling."

Before I dissect this sentence and suck the magic out of it, I just want to say, damn. You can see and feel the uncanny nature of the woods. The images are specific, but open-ended. The phrase "long-dead relative" is like a fill-in-the-blank, charging the whole sentence with emotion.

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Wallace takes something that you've always seen in black-and-white and turns it into a color photo.

In the circle of writers I know online, we use an acronym called "POP Writing"– Personal, Observational, and Playful. Wallace is a master at crafting memorable observations. He uses relatable metaphors, makes unlikely associations, and looks under the rocks that most people walk past. He re-wires how you see the world. Pencil in hand, I scribbled all over his essay to figure out how he does it.

Here are 6 ways you can inject memorable observations into your writing (also, warning: R-rated excerpts ahead):

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At 387 feet above sea level, I can see the lagoon and the cascades of vinyl houses. I conduct my “annual review” on the hike up, and set a goal at the peak. It’s one of the few systems in my life that works. There’s no better way to navel-gaze— on top of Quinn’s Hill, exploding with light— in the Morning Dew of the new year... that is, if I get there on time.

Like a Sergeant, my backpack is ready, weeks in advance, with everything I need: a pre-rolled joint, 2 spiral bound notebooks, 4 “space” pens, a beanie, a thermal under-shirt, a plastic water bottle filled with gasoline (for the bonfire), and of course, a .44 magnum in case of incidental bears.

I’m usually late. I blitz-write into these notebooks, as I walk, uphill, without looking. All my potential futures are inked in a special kind of hieroglyphic chicken-scratch— a language not even I can decipher. The act of putting pen to paper is merely a formality. All of my goals end up in the same place: the bonfire on top of Quinn's Hill. Goals are dangerous. Their symbolic destruction is important to me. They whisper sweet visions, but they’re trojan horses— poison cloaked in purpose... What was once a sneaking suspicion to me is now obvious: Goals are cancer of the imagination. A Castle in the Sky is the worst kind of tumor. It fogs your awareness and prevents growth. It blinds you to obvious vistas of possibility.

Let us instead carve into the future like the nomadic men and woman that roamed before the original sin of agriculture— with insatiable hunger... I won’t pretend that my whole existence doesn’t mooch off the tailwinds of the prefrontal cortex. But let us at least pick one worthy impulse— ONE THING that leads us to the same place where Goals claim to deliver.

My impulse for the year is straightforward: learn to write like a force of nature— like a fat old sunflower in the sky, rising everyday, to deliver words to anyone who cares to look up, inducing primal wonder in some, and temporary blindness in others... Trust that writing bends reality, and the rest will work itself out... 7:19 am, Quinn's Hill caught fire, melting the upcoming year into an empty canvas— a blank slate, for some unnamed wordsmith to jangle within.

Virginia Woolf knocked out sentences that could stand alone as their own atomic essays. Upwards of 200 words, the sights, and sounds, and things she heard, they burst out from her mind, in between commas and semi-colons, giving you the chance to vacation in her daydreams. Woolf would "sketch" scenes, but her British rambles had a method. She was a master at building patterns and then breaking them, in a way that was unexpected.

This >

This >

Still this >

Most likely this >

Most definitely still this >

This >

This >

THAT! Jesus, that?

She was a comedian, but joked through beauty and horror. Her work is filled with dramatic run-ons, where all signs point in one direction, but then as soon as you feel oriented, she hits you with a curveball.

"Mrs. Dalloway" is recognized as the origin of stream-of-consciousness novels. Behind the rambles, she had an intuitive sense of how to throw in logic twists, which is where she often hid her most important ideas.

By analyzing a few of her sentences, we can learn how to use structure to shine spotlights on the ideas that matter.

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• How do you freeze your consciousness through words?

• How do you immerse readers in a scene?

• How do you collapse categories and explore your full range of interests?

• How do you experiment with sentence construction?

• How do you catch both the fish and the whale?

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“Breakfast is the only meal of the day that I tend to view with the same kind of traditionalized reverence that most people associate with Lunch and Dinner. I like to eat breakfast alone, and almost never before noon; anybody with a terminally jangled lifestyle needs at least one psychic anchor every twenty-four hours, and mine is breakfast. In Hong Kong, Dallas or at home — and regardless of whether or not I have been to bed — breakfast is a personal ritual that can only be properly observed alone, and in a spirit of genuine excess. The food factor should always be massive: four Bloody Marys, two grapefruits, a pot of coffee, Rangoon crepes, a half-pound of either sausage, bacon, or corned beef hash with diced chiles, a Spanish omelette or eggs Benedict, a quart of milk, a chopped lemon for random seasoning, and something like a slice of Key lime pie, two margaritas, and six lines of the best cocaine for dessert… Right, and there should also be two or three newspapers, all mail and messages, a telephone, a notebook for planning the next twenty-four hours and at least one source of good music… All of which should be dealt with outside, in the warmth of a hot sun, and preferably stone naked.”

As I read it, she was hooked, with intermittent gasps, eye-widens, and crack-ups. Our table was soon filled with plates, and it felt wimpy compared to the legend we just heard. This breakfast ritual is absurd enough to grab anyone's attention. But behind the hyperbole is an unconscious mastery of craft. It's the difference between a crazy idea and a classic.

This was written in 1979, six years after Fear and Loathing in Las Vegas, and two decades after that time where he notoriously rewrote Hemmingway novels (while speaking them out loud). I imagine this 215 word piece was blurted out in around 25 minutes, perhaps under the influence of eggs and cocaine, and in a rush to meet a deadline for Lapham's Quarterly.

Even if the act of making this happened in a flash, there's a lot we can learn from carefully analyzing Hunter's writing mechanics. We're about to dive deep into an analysis that is six times longer than the piece itself. The goal here is to identify the rational patterns behind emotional resonance.

• If our essay contains a series of ideas, we should consider not just how we arrange them, but how far we unpack each one.

• I know what it feels like when a sentence starts normally, but then hits you in the face with a punchline from left field.

• We can write sentences at near infinite length if we consider how each phrase builds momentum into the next one.

• Capitalizing words that typically don't get upper-cased can bring flat words to life, especially if you add context clues.

• When you repeat a distinct phrase at the beginning and end of an essay, it implies resolution, and also gives the opportunity for a surprise ending.

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