Essay Architecture

Every essay faces the same design problems, so quality can be judged. Michael Dean scores essays from 1 to 5 on 27 patterns, sometimes 81 criteria since each pattern has three more. His case rests on thousands of new writers' drafts, a hundred classic essays and almost a million of his own words.

Wallace's "Consider the Lobster" and Orwell's "Shooting an Elephant" are opposites in style, yet both score about nine out of ten. Dean argues writers need words for what is wrong, because "no wrong answers" stops helping once a draft feels off and they cannot say why.

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The patterns sit under three dimensions: idea, form and voice. Idea is material, thesis and title. Form is paragraphs, structure and tension. Voice is spirit (subtext and tone), sound (repetition, rhyme, rhythm) and sight (imagery).

Once the thesis is known, some material must be cut, and the title compresses the thesis into one package that gets a reader in. Dean uses "tension" in place of "storytelling" and says spirit is the element AI handles worst.

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A pattern is a question, not a template, so many answers work. The model is Christopher Alexander's pattern language, which maps 253 recurring design problems in architecture. The hero's journey is one of hundreds of valid sequences.

Dean's metaphor: the Guggenheim and the Fifth Avenue Apple Store look like opposites, but flattened into section drawings both are built around a central atrium with a skylight, perimeter circulation and dim core rooms. The Whitney is confusing because it skips these patterns.

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Learn your genre's basics before chasing taste. Taste blindness means clinging to one solution, such as always using the hero's journey, confessions or short blocky paragraphs, while losing the fundamentals. Zooming out to the underlying patterns breaks the rut.

Dean compares it to curvy software-designed buildings with no obvious front door. "Start with the basics and then from there your taste will arise."

How I Write▶ 1:13:11

Start from one tangible microcosm that stands for a bigger idea. Wallace narrows animal ethics to lobsters, then Maine, then the 2002 Maine Lobster Festival, so the reader reaches the conclusion unpreached. Umberto Eco's version is "pick one volcano": from volcanoes down to Popocatépetl.

Zooming in only works on a thing that represents more than itself. Writers' scope tends to balloon from a thousand words to 15,000, and David Perell's top lesson for students was to write about fewer things.

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Every paragraph needs a hook that opens a loop and a punchline. Wallace's lobster paragraph opens with lobsters as giant sea insects, adds reasons (ancient, ugly, garbage men of the sea) and ends on "sometimes each other", a cannibal joke never stated.

Reading is friction, so a broken loop loses the reader. When editing, Dean checks each paragraph's opening frame and last-line payoff; weak ones start without a frame, so the reader does not know why they are reading.

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Vary the resolution of detail to make dense passages readable. Wallace packs 37 details into one paragraph: 17 general (carnival rides, lobster ravioli), 16 absurdly specific (the William D. Atwood memorial crate race), plus numbers like 25,000 pounds of lobster and 100,000 attendees.

He clusters them by music, attractions and food. Only 3 of the essay's 33 paragraphs are this maximal; in unedited essays the density becomes unstable.

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Put yourself on the page without being confessional. Dean's experience pattern has three parts: biography (a camera in the room), interiority (what is in your head that film cannot show) and outlook (a nonstandard belief).

Wallace closes an observational paragraph with "Your assigned correspondent saw it all, accompanied by one girlfriend and both his own parents." Outlook must be earned upstream by showing the experiences and inner calculations behind the belief, not stopping at "I believe this".

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Write the first draft for yourself and the second for readers. In the first draft, ignore patterns and chase the material to discover what it is. Once you know the specific question, use structure and craft to make it legible; Dean calls the framework an editing philosophy, not a drafting one.

He draws on Frank Lloyd Wright's emergent architecture, where each site gets a new design instead of a stamped floor plan.

How I Write▶ 45:22

Edit one pattern per pass, highlighting it in a single color. Pick one pattern, such as voice, highlight every place it shows up in orange and ignore structure and thesis for that pass. Sections with no highlights show where the voice vanishes, so rewrite those.

"You can have a razor lens just on one pattern at a time."

How I Write▶ 51:30

Rewrite a weak paragraph from scratch rather than patching it. You cannot mechanically add voice to a three-out-of-ten paragraph. Try it again with a few patterns in mind, such as more sound or imagery, then judge, and loop until one version works.

Reverse engineering famous voices is easy; finding your own takes repeated attempts.

How I Write▶ 52:22

Intuitive greats drilled the boring basics first. Jerry Garcia practiced scales 10 hours a day, Kerouac wrote a million words of plain novels before his scroll, Hunter S. Thompson retyped The Great Gatsby and Picasso copied classical masters.

Dean uses the 27 patterns to find which basics to shore up, practicing them bit by bit until the system can be forgotten. "You need to be in your head to understand how it works in order to eventually get out of your head."

How I Write▶ 47:07

AI can spark and compress drafts but cannot yet judge quality. In Dean's prompt tests, AI scoring of writing quality is about 50% accurate, close to a random guesser. Asked to rewrite Paradise Lost and judge both versions, it preferred its own slop.

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Writing is worth doing for what it does to the writer. Dean's architecture school banned software for three years, and he hand-drew a 4x5 ft map of Manhattan out of dots; that slow work taught him how buildings go together.

He imagined AI that is brilliant, popular and able to replicate him, and concluded he would still write, to make sense of his life.

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