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:

• Michael’s Website
• Substack
• X/Twitter Profile

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