Infinite Loops Episode 281: Michael Dean — The Architecture of Essays

Date: September 11, 2025
Host: Jim O'Shaughnessy
Guest: Michael Dean

Episode Overview

In this episode of Infinite Loops, host Jim O’Shaughnessy sits down with Michael Dean—architect-turned-writer and O’Shaughnessy Fellow—to dive into the conceptual and practical underpinnings of Michael’s groundbreaking "Essay Architecture." Dean explains how his background in architecture shaped his approach to essay writing and editing, resulting in a comprehensive framework and a software tool designed to democratize mastery of composition. They discuss the hidden patterns of nonfiction, the future of writing education, applications for AI in writing, the perennial value of essays, and the ways tools like Dean’s can level society’s intellectual playing field.

Key Discussion Points & Insights

1. From Architecture to Writing (02:16–04:43)

• Dean’s Architectural Roots: Michael maps his transition from architecture to writing, noting the field’s emphasis on breaking down forms into elemental patterns—a concept he brings to writing.
• Deficiency in Writing Education: Identifies a lack of holistic frameworks for teaching composition. Dean believes, “Composition is an important word… it is a teachable thing.”
• Borrowing from Pattern Languages: Inspired by Christopher Alexander’s work, he creates a “pattern language” for essays—frameworks to guide writers in mastering composition, all teachable in under a year.

2. The "Essay Architecture" System (06:24–11:12)

• Scoring and Flexibility: Dean details a 1–5 rubric for 27 essay patterns, embedded within three broader dimensions (idea, form, voice).
  • Score 5 = mastery, 1 = missing, 3 = publishable.
• Not Just Templates: Stresses avoiding rigid templates, advocating for creative, context-sensitive application:
  • “An artist is someone who is not defaulting to their templates… always trying to reinvent.” (06:24)
• Analogy with 'Arrival': Readers have bandwidth limits; essays must move from “uncertainty to certainty,” and “imbue [reading] with sight and sound and spirit” for a sensory, nervous-system-level impact. (08:13)

3. Avoiding the Trap of "Style Kits" (09:32–11:12)

• Local vs. Universal: Warns that shared pattern languages can lead to homogeneity—“global styles.” Emphasizes the need for individual idiosyncrasy:
  • “The risk is the development of a global style… becomes boring because everyone’s using them.” (10:08)
  • Draws parallels to regional variations (e.g., essays reflecting Greenwich, CT vs. Queens, NY).

4. Author Evolution: Twain, Joyce & Experimentation (11:12–19:59)

• Writer’s Journey: Discusses how writers’ styles change over careers, using Mark Twain and James Joyce as examples.
  • “When Twain's audience changed, his general style warped with it.”
  • Essay Architecture focuses on primitives; it’s up to writers to break or reinterpret them.
• Room for Outliers: On Joyce: “Once you master composition, you kind of get bored… you then have license to break it.” (16:29)
• Essay Competition: Reveals they're using Dean’s tool to score submissions for an upcoming contest, blending AI-quantitative assessment with human, intuitive judging.

5. Democratizing Good Writing: Education & Admissions (21:10–30:15)

• Leveling the Playing Field:
  • Current admissions system favors the wealthy: “25% of incoming Harvard students use professional admissions consultants, spending up to $3,000.” (24:39)
  • Dean’s tool aims for quality editing at <$10/essay.
• Tracking Progress, Ensuring Integrity: Unlike ghostwriting or detection tools, Essay Architecture tracks how a student improves, making learning (and fair admissions) accessible to all.

6. Technology in Education: Resistance & Acceptance (31:29–39:13)

• Innovation Fears:
  • O'Shaughnessy compares resistance to AI to historic reactions to calculators, photography, and refrigerators.
  • Dean shares personal stories of being banned from using technology during architecture studies—ultimately appreciating the benefit of manual learning:
    • “If school doesn't teach the slow, hard, boring, ancient fundamentals, there's going to be no intelligence to amplify.” (33:33)
  • Advocates for a “two sandbox” model: one for granular, manual skill drills, one for integrating modern tools (“the best of both worlds”).

7. Motivation, Gamification, and Systemic Change (39:13–44:37)

• Gamifying Writing Practice:
  • Making granular practice fun and competitive can motivate learners.
  • Cites architecture school’s blend of autonomy, social stakes, and resource access.
• Role of Curation in the Age of AI:
  • O'Shaughnessy: “We’re going to need curation apps... Show me the best one and give me summaries of the other ones.” (46:38)
  • Dean envisions real-time newsletters highighting superb essays, aided by his tool’s quality-based rankings.

8. Writing as the Foundation of Thinking (44:37–53:01)

• Writing Reveals Thought:
  • “Writing is maybe the most important aspect of learning kind of what you think.”
  • O'Shaughnessy: The act of articulating ideas exposes which are sound and which are not.
• AI as Editorial Aid: Both discuss using AI—never for ghostwriting but for constructive, even adversarial, feedback and improvement.

9. The Pattern Language & History of the Essay (50:41–55:46)

• Origin of Standard Essays:
  • The 5-paragraph essay stems from medieval European law schools, not optimized for curiosity or individuality.
  • Paul Graham’s critique is cited; the system prioritizes producing "legal defenses" over exploratory thought.
• Composition vs. Quality:
  • Essay Architecture can reveal patterns, but “Quality has a statistical aspect, but it’s not the whole story.”
  • “Once you master [composition], you have license to break it and have a low scoring essay because you’ve earned that.” (16:29)

10. Science, Metrics & Human Judgment (55:46–65:26)

• Precision in Scoring:
  • Dean: AI system can reach 99% precision; the best humans hit 73%.
  • O'Shaughnessy: Quantitative models, especially when consistently applied, often outperform humans over time.
  • Both advocate for the "centaur" model: human + machine, where AI aids—never replaces—insightful human critique.

11. Editing, Rewriting, and Feedback Loops (61:27–67:25)

• Editing as Transformation:
  • Dean: "Editing is not rewiring words, it’s rewiring synapses.” (64:10)
  • Advocates for whole-draft rewrites, not just line edits—where real cognitive shifts happen.
• AI as Editor, Not Cheerleader:
  • Gives the example of prompt engineering to turn AI into a “vicious critic” rather than a sycophantic coach, revealing constructive blind spots.

12. Education Philosophies: Intuition, Osmosis, and Deliberate Practice (69:09–73:23)

• Writing Is Learned, Not Innate:
  • Speaking comes naturally; writing requires deliberate study and repeated, conscious practice.
  • “Most people just have bad Intuition, right? Especially when it comes to writing. That’s why we all use clichés.”

13. Encouraging Curiosity, Immersive Learning, and New Tools (73:23–83:19)

• Conditional Logic and Questioning Certainty:
  • O'Shaughnessy celebrates probabilistic, conditional thinking over deterministic, one-right-answer mindsets (“certitude is a kind of death”).
• Surface New Voices:
  • Discuss possibility of leveraging Dean’s tool to discover and amplify emergent talent from obscure corners of the internet or society.

14. Future Projects: Dictionaries, Thesauri, and Beyond

• Dean’s Vision:
  • Outlines plans for a new kind of thesaurus structured around core synonym-antonym pairs and nuanced qualifiers.
  • Envisions a multi-decade project to map core archetypes and elevate writing and thinking at every layer: “mastery of composition, of diction, and of philosophy.”

Notable Quotes & Memorable Moments

• On Writing as Pattern Language:
  • “Every pattern has a whole dictionary of types… the risk is a global style where everyone is using the same forms… and then it just becomes boring.” —Michael Dean (10:08)
• On Composition:
  • “Once you master composition, you have license to break it and have a low scoring essay because you’ve earned that.” —Michael Dean (16:29)
  • “It’s not writing for them, but it’s giving them all the right questions and ideas for them to rewrite the draft at a higher form.” —Michael Dean (24:39)
• On AI and Education:
  • “If school doesn’t teach the slow, hard, boring, ancient fundamentals, there’s going to be no intelligence to amplify.” —Michael Dean (33:33)
  • “We are deterministic thinkers living in a probabilistic world, and hilarity or tragedy often ensue.” —Jim O’Shaughnessy (91:54)
• On Editing:
  • “Editing is not rewiring words, it’s rewiring synapses.” —Michael Dean (64:10)
  • “I hate writing. I love having written.” —Jim O’Shaughnessy quoting Dorothy Parker (65:44)
• On the Value of Essays:
  • “You could have written a treatise on animal ethics and it would have been very boring… instead [Wallace] brings you to him at a specific lobster festival… and then he gets into all these philosophical dimensions.” —Michael Dean on David Foster Wallace (55:46)
• On AI Editorial Feedback:
  • “It’s like a kill-your-darlings GPT.” —Michael Dean (76:05)
• On Motivating Change:
  • “Everybody wants progress but nobody wants to change.” —Jim O’Shaughnessy (39:13)
• Emperor of the World: Dean’s Two Inceptions:
  • “Write down 100 of your thoughts in a day… you’ll see the patterns in your thinking and improve from that.”
  • “Become a master of conditional logic around your own identity… It’s like the kernel of cognitive liberty.” (88:09)

Important Segments & Timestamps

• Background & Motivation (02:16): Dean’s path from architect to writing coach.
• Pattern Languages & Frameworks (04:43, 06:24): How architectural analysis informs essay composition.
• Rubrics and Scoring (06:24): 1–5 scoring, creative flexibility, and software implementation.
• Creativity vs. Templates (10:08): Risks of global style, local idiosyncrasy.
• Audience and Author Evolution (13:24): Twain and Joyce, writer’s developmental journey.
• AI as Coach, Not Ghostwriter (19:59, 24:39): How Essay Architecture aids but doesn’t do the work.
• Admission & Fairness (24:39): Democratizing essay writing for college applicants.
• Technology Pushback (31:29): Historic resistance to innovation.
• Manual Skill-Building & Sandboxes (33:33): The necessity of both hands-on practice and tech amplification.
• Gamification in Learning (39:13): How to motivate reluctant learners.
• Editing Is Where Growth Happens (64:10): The psychological hurdle and the transformative power of editing.

The Essay Architecture Competition

Details (79:51–82:19):

• Begins September 15, 2025; runs ~6 weeks.
• $10,000 grand prize—largest open essay prize globally for accessible essays.
• Prompt: “Write an essay about a personal experience microcosmic of something that unfolded in [the year] 2025.”
• Open to all; submissions benefit from feedback, not just winning.

Michael Dean’s Future Projects (83:19–86:19)

• Ongoing: Improving Essay Architecture, scaling curation and competitions.
• Upcoming: Building a new, more useful thesaurus/dictionary and mapping “archetypal ideas” across history.
• Personal: Expecting a daughter at year’s end!

Where to Find Michael Dean

• Substack: michaeldean.site
• Essay Architecture: sarchitecture.com (tool, book, competition details)

Concluding Message

Dean and O’Shaughnessy wrap with a mutual enthusiasm for tools and philosophies that foster genuine learning, an embrace of both human and machine insight, and a call to level up how society teaches, writes, and thinks. Michael Dean invites everyone to experiment with the deliberate practice of writing, challenge stale educational orthodoxies, and use frameworks like his to supercharge their intellectual growth.

End of Summary