Michael Dean — architect-turned-writer, O’Shaughnessy Fellow, and creator of Essay Architecture — joins the show to explore the hidden structures beneath nonfiction and why essays, like buildings, can be designed with patterns rather than left to inspiration.

We discuss the origins of Essay Architecture, Michael’s 27-pattern framework that maps essays across Idea, Form, and Voice, and how to make craft teachable and AI feedback useful without replacing the writer. Along the way, we dive into architecture school critiques, why publishable doesn’t mean perfect, how editing rewires thinking, and the cultural risks if we keep treating writing as vibes instead of patterns.

I hope you enjoy the conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack.

Important Links:

Show Notes:

The Architecture of Essays: from Design School to Writing Frameworks
The Pattern Language: Idea, Form, and Voice
Local Nuance vs Global Stylekits
Fundamentals before Breaking Rules: Joyce, Picasso, the Beatles
Quality Without a Name
Leveling the College Playing Field
The Two Sandboxes of Fundamentals and Amplification
Gamification, Play and Motivation
Beyond the Five-paragraph Essay: Emerson and AI in Education
Scoring Great Essays: Why David Foster Wallace takes Three Top Spots
How Writing Colonized the brain
Editing as Belief-rewiring: Why Writers Avoid It and Why Math Helps
The King of Biases: Confirmation Bias
Michael as Emperor of the World

Books Mentioned:

Works on Wall Street; Jim O’Shaughnessy
Essay Architecture (in progress) ; by Michael Dean
A Pattern Language; by Christopher Alexander
The Best American Essays 2024 Anthology; by Wesley Morris and Kim Dana Kupperman
Consider the Lobster; by David Foster Wallace
The White Album; by Joan Didion
Shooting an Elephant; by George Orwell
Portrait of an Artist as a Young Man; by James Joyce
Finnegan’s Wake; by James Joyce
Towards a Golden Age; Paul Graham
The Limits of Scientific Reasoning; by David Faust
The WEIRDest People in the World; by Joseph Henrich

Michael Dean — The Architecture of Essays (EP. 281)

Infinite Loops