All Segments
You’ve Never Seen Writing Visualized Like This — Michael Dean
52 segments available
Architect Michael Dean breaks down the hidden patterns behind the great essays of our time. In this video, we go over his 27-point framework that makes up every world-class piece of writing and how he uses the same system to analyze the Guggenheim and Apple Store. We also talk about what skills will still matter as AI continues to improve and why learning to write might be more important than ever. Enjoy! A few links: 1. Join the Essay Architecture beta: https://essayarchitecture.com/ 2. Follow Michael Dean on Substack: https://www.michaeldean.site/ 00:00:00 Intro 00:00:41 Is writing quality objective? 00:03:18 Grading essays with AI 00:06:07 Guggenheim vs. Apple Store 00:08:33 How great writers start 00:11:37 Practice vs. performance 00:16:12 Editing for voice 00:25:30 Getting feedback like a comedian 00:29:06 A map of writing patterns 00:37:11 Rhythm, sound, and style 00:44:25 Wallace vs. Orwell 00:54:20 Wallace’s 37 examples 01:00:17 Three pillars of personal writing 01:05:51 Intention creates tension 01:12:18 What makes a great essay 01:20:34 AI’s influence on writing 01:28:16 Should schools ban ChatGPT? 01:31:11 Writing’s deeper meaning 01:39:47 How work writing will change 01:44:49 Personal writing vs. AI 01:50:28 Why writing still matters Hey! I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible. Follow me Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470 Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv X: https://x.com/david_perell
Segments Timeline
The Antidote to Writing Frustration
In this segment, David Perell introduces Michael Dean, a former architect turned writing expert, who offers a unique perspective on the writing process. Michael's visualization techniques provide insights into improving writing quality, helping writers identify and address their blind spots. He also hints at a transformative vision of how AI will influence writing mastery.
"You ever sit down to write and you just feel like something's off with your writing, but you can't quite pinpoint what it is? Well, this episode is the antidote. And my friend Michael Dean, he's a for..."
Is Writing Quality Objective?
Michael Dean discusses the dual nature of writing quality, emphasizing that while grammar has objective rules, the essence of what makes writing great is subjective. He argues that understanding an objective system of quality can help writers recognize their weaknesses and improve their craft, addressing the common frustrations new writers face.
"writing quality is objective? So it's definitely both objective and subjective. I just think that objectivity rationality reason they're all severely underrated in our culture of writers. So when it c..."
Analyzing Writing Like Architecture
Michael draws parallels between writing and architecture, explaining how both disciplines rely on fundamental design principles. He introduces his concept of 'essay architecture,' which includes scoping ideas, setting boundaries, and crafting a cohesive voice. This framework allows writers to analyze their work systematically, similar to how architects evaluate buildings.
"Yeah. Tension is what I used instead of storytelling. But in my mind, paragraphs are the atomic unit of form. We can talk about that because I know people have some trauma with five paragraph essays. ..."
Guggenheim vs. Apple Store: A Comparative Analysis
In this segment, Michael compares the Guggenheim Museum and the Apple Store, highlighting their architectural differences and similarities. He explains how architects use section drawings and diagrams to analyze structures, revealing that despite their contrasting appearances, both buildings share a central atrium design that enhances user experience.
"want to see how you analyze it and how you break it down because I I want to be convinced. I want to be convinced that we can take something where I'm like, "Oh, no. It's really good, but I think it's..."
Finding Common Ground in Different Essays
Michael introduces two essays, 'Consider the Lobster' by David Foster Wallace and 'Shooting an Elephant' by George Orwell, to illustrate how different writing styles can still adhere to the same fundamental principles. He discusses how both essays excel in their respective approaches while mastering the core elements of effective writing.
"they have very subtle ways different but they're ways to let light in without it directly hitting the space. All right. So when you reduce the complexity and just isolate certain features, you actuall..."
The Power of Specificity in Writing
Michael emphasizes the importance of specificity in writing, using David Foster Wallace's essay as an example. He explains how focusing on a particular topic, like the Maine Lobster Festival, allows writers to convey broader ideas more effectively. This approach helps avoid the common pitfall of overly broad writing.
"lobster. That great. That sound good? Yeah. So, what is the one thing if we're going to deconstruct this? What is the one thing that we can learn from it? Yeah, I think there's something very simple u..."
The Pick One Volcano Principle
Michael shares Alberto Ekko's 'pick one volcano' principle to illustrate the necessity of narrowing one's focus in writing. By zooming in on a specific subject, writers can explore complex ideas in depth, leading to richer and more insightful essays that resonate with readers.
"better. Yeah. There's another uh theory that's really helpful for this. So Alberto Ekko, he wrote a book called How to Write a Thesis. Uh and he has something called the pick one volcano principle. An..."
Maximalism vs. Minimalism in Writing
In this segment, Michael contrasts maximalist and minimalist writing styles, particularly in the context of David Foster Wallace's work. He discusses how effective paragraphs can serve as atomic units of composition, emphasizing the need for engaging hooks and impactful conclusions to maintain reader interest.
"to zoom in cuz you said something earlier about maximalism and minimalism. Can you break down how the maximalism of David Fostwallis happens? I actually really want to know cuz I love his writing, but..."
Breaking Down a Paragraph
In this segment, Dean analyzes a paragraph about lobsters, illustrating how effective writing can reveal unexpected truths. He explains how the opening sentence sets the stage for a surprising conclusion, using the example of lobsters as 'giant sea insects' to challenge readers' perceptions of luxury food. The discussion highlights the importance of subtext and the reader's journey through the paragraph.
"they're going to say, "Why am I going to keep going?" Reading is friction. Yeah. So, I want to read a simple paragraph and just kind of show you how it kind of fits that format. Cool. So, here it is. ..."
Crafting Engaging Writing
Michael Dean emphasizes the importance of crafting engaging paragraphs by ensuring that the opening sentence creates a sense of mystery and the closing sentence delivers a powerful example. He discusses common pitfalls in writing, such as failing to set the frame for the reader, and stresses the need for clarity and intrigue to maintain reader interest.
"here is what it's that he opens with a sentence that both explains what we're going to read and there's a bit of mystery to it. Then he kind of flows through a few different points. It's the strongest..."
Maximalism in Writing
Dean introduces the concept of maximalism in writing, using David Foster Wallace's technique of incorporating numerous specific details in a single paragraph. He explains how Wallace's approach creates a dynamic reading experience by alternating between general and specific examples, ultimately enhancing the richness of the narrative.
"in my mind, that's a fairly straightforward paragraph. It's four sentences and he's kind of listing off examples. It's it's pretty traditional in terms of what a paragraph is. And talk to me about Dav..."
The Power of Detail
In this segment, Dean explores how David Foster Wallace's writing style captures reality in vivid detail. He discusses the balance between general and specific examples, illustrating how varying the resolution of details can keep readers engaged. Dean highlights the importance of structuring details in a way that creates a cohesive and immersive experience for the reader.
"paragraph. In one paragraph if you were to just list them off I saw a parade, I saw lobsters. I saw this. I saw that. It could be very repetitive and mechanical and boring. But there's a few ways that..."
Observational vs. Personal Writing
Michael Dean delves into the intersection of observational and personal writing, emphasizing the need for writers to infuse their unique perspectives into their observations. He discusses how personal experiences can enhance the narrative, making it relatable and engaging while maintaining a sense of authenticity.
"reality effect in his writing. Mhm. And you would imagine walking around the festival, it's a bunch of random noise, but he's trying to cluster the details. He starts with, let's talk about the musica..."
Defining Personal Writing
In this segment, Dean defines personal writing through the lenses of biography, interiority, and outlook. He explains how these elements contribute to a deeper understanding of the writer's experiences and beliefs, encouraging writers to share their unique perspectives while remaining authentic and relatable.
"this, how does the observational merge with the personal? So how can you observe something as a writer in a way that feels personal and unique to you? Because usually when we think of observations lik..."
Common Pitfalls in Personal Writing
Dean discusses common pitfalls in personal writing, such as being overly sentimental or generic. He emphasizes the importance of grounding personal narratives in specific experiences and details, ensuring that the writing reflects the writer's unique voice and perspective.
"myself I was writing personal, but I wasn't really. Um so this definition might help. And so one of my patterns is experience, right? And then the question is, well, what is an experience? And so I br..."
Comparing Writing Styles
In this segment, Dean compares the writing styles of David Foster Wallace and George Orwell, highlighting how both authors utilize biography, interiority, and outlook in their essays. He illustrates how their approaches differ while still achieving powerful personal narratives, showcasing the versatility of personal writing.
"biography, interiority, outlook. Break them down for me. Yeah. So, this is showing how these two essays, consider the lobster and shooting an elephant, they both have these three things, but they exec..."
Intention, Obstacle, and Consequence
In this segment, Dean breaks down the essential components of storytelling: intention, obstacle, and consequence. He illustrates how these elements work together to create tension and lead to a climactic moment in writing. By using relatable examples, he demonstrates how writers can structure their narratives effectively to engage readers.
"this is in shooting an elephant, right? And so in the beginning you understand the who this character is, right? So you understand that he's stuck between an empire he doesn't want to serve. He's tryi..."
Questions as a Writing Framework
Michael Dean discusses the significance of framing essays around questions. He explains how identifying the core question can guide the writing process and enhance clarity. This segment emphasizes the importance of refining questions during drafting to improve the overall quality of the writing.
"work together to really these are the three kind of criteria of a conflict and they and they work in sequence too, right? You have to I mean of course you can have previews of consequences in the begi..."
Invisible Questions in Writing
In this insightful segment, Dean reveals how effective writing often contains invisible questions that guide the reader's understanding. He analyzes Orwell's 'Shooting an Elephant' and a personal writing example to illustrate how subtext can create a compelling narrative structure. This approach encourages writers to embed questions within their hooks to engage readers from the start.
"Wallace, I've dissected two of his essays according to questions. And what he actually has is a whole hierarchy, his three tiers of questions beneath his structures. Right? So if we can go through tha..."
The Role of Tension in Writing
Michael Dean emphasizes the role of tension in both storytelling and essay writing. He explains how tension can arise from character conflicts or the exploration of ideas. This segment highlights the importance of maintaining tension throughout a piece to keep readers engaged and invested in the narrative.
"this is a good thing to study than just sort of have in the background of your mind versus if you want to write better, get clear on this. Write it down. Where does that boundary exist? Yeah. I'd say ..."
Crafting Effective Hooks
In this segment, Dean discusses the importance of crafting effective hooks in writing. He shares strategies for embedding questions within the opening lines to draw readers in. By analyzing examples, he illustrates how a well-crafted hook can set the stage for the entire piece, creating intrigue and guiding the narrative.
"that. Yeah. And that's why I call the element tension instead of storytelling. People think stories are about characters, but there are there's tension behind characters and there's tension behind ide..."
Poetic Prose and Sound in Writing
Michael Dean explores the concept of poetic prose, discussing how sound and rhythm can enhance writing. He shares examples of how writers can use phonetic resonance to create a more engaging reading experience. This segment emphasizes the importance of auditory elements in writing and how they contribute to the overall impact of a piece.
"subtext of the hook. So, tell me this. People talk about rhyming in poetry, but do you see it show up in in pros? Definitely. So, so rhyme is one of these 27 patterns. It covers alliteration, too. It'..."
Editing for Rhythm and Flow
In this final segment, Dean discusses the editing process, focusing on how to refine writing for rhythm and flow. He shares techniques for selecting words that enhance the musicality of prose. This segment highlights the importance of auditory editing in creating a polished and engaging final product.
"process is basically happening intuitively whenever you're listening to a piece of writing? I think even when you're reading it silently, that your inner ear is is picking up on pros that is phonetic...."
The Writing Process: From Draft to Reader
In this segment, Dean shares his unique approach to the writing process, advocating for a first draft that is personal and exploratory, followed by a second draft tailored for the reader. He draws parallels between writing and organic architecture, emphasizing the need for flexibility and adaptation in both fields.
"writing process. Let's talk about where you start, where you end, how you edit. And I want to hear just from from your method based on all the writers that you've studied, all the writers that you've ..."
Practice Analytically, Perform Intuitively
Michael Dean discusses the balance between analytical practice and intuitive performance in writing. He uses examples from music, particularly The Grateful Dead, to illustrate how deep practice informs spontaneous creativity. This segment highlights the importance of foundational skills in achieving fluidity in writing.
"what I'm hearing you say because a lot of your method is actually very analytical, very objective, but what you're saying here is yo, but at the beginning just just right. Get stuff out there. Let it ..."
Mastering the Basics: Picasso and Kerouac
Dean reflects on the importance of mastering foundational skills in writing, drawing parallels with artists like Picasso and writers like Jack Kerouac. He emphasizes that great creativity often stems from years of disciplined practice and understanding of traditional forms before developing a unique style.
"And it's almost like you need to be in your head to understand how it works in order to eventually get out of your head. Dude, I love this. I mean the way that I would think about it, this is obviousl..."
The Role of Voice in Writing
In this segment, Dean articulates the significance of voice in writing, explaining how it shapes the reader's experience. He discusses the friction of reading and the need for compelling language that resonates on a deeper level, allowing readers to connect with the writer's perspective.
"form and style. Totally. And the way I see it is my project essay architecture is an attempt to map out here are the boring basics that are probably worth studying and by by kind of having patience to..."
Finding Authenticity in Writing
Michael Dean shares his journey towards finding his authentic voice in writing. He discusses the challenges of self-consciousness and the importance of writing without the pressure of an audience. This segment emphasizes the value of personal reflection and the freedom that comes from writing for oneself.
"you get the sense, oh, there's another person at the other end of this. And I think a lot of good writing is almost putting on somebody else's brain for some time, seeing the world how they see it, th..."
Feedback Like a Comedian
Michael Dean outlines his unique method for receiving feedback on his writing, likening it to how comedians test their material. He emphasizes the importance of granular feedback and how he uses color coding to track reader responses, ensuring that he focuses on what resonates with his audience.
"might not blast the audience of essay architecture but they're all there and that's where I do a lot of my um kind of like the edge of my thinking happens in places that are less public and so it lets..."
Reading with Purpose
Dean discusses his approach to reading drafts, advocating for an initial read-through followed by a focused analysis of highlighted sections. He explains how this method helps him extract principles that can enhance his own writing, ultimately contributing to the development of his essay architecture framework.
"that's a sign to me that, hey, maybe I should cut this or or compress it. Uh, and this is effectively how stand-up comedians kind of like test jokes on a circuit. They will take the same joke and they..."
Understanding Pattern Language
In this segment, Dean introduces the concept of 'pattern language' as developed by Christopher Alexander. He explains how this framework maps universal patterns in architecture and how it can be applied to writing, allowing writers to identify interconnected patterns that enhance their work.
"organize all these things. When what is a pattern language? Explain that. So, that's a book by Christopher Alexander in uh 1978. And basically it's him trying to map the universal patterns across all ..."
The 27 Patterns of Writing
Michael Dean shares his 27 patterns of writing, contrasting them with Alexander's 253 patterns. He emphasizes the importance of mastering these patterns to create timeless essays that resonate with the human psyche, highlighting the versatility and depth of the essay as a form.
"um web of of design constraints. Yes. And the thing is with these patterns, once you see them, you kind of can't unsee them. So one of my favorite ones is that a balcony that is less than six feet dee..."
Creating Tension in Writing
Dean discusses the concept of tension in writing, explaining how it differs from storytelling. He breaks down three key patterns—conflict, threads, and hook—that writers can use to enhance tension and engagement in their essays.
"if I want to I really like what you're saying about tension. Tension is opposed to storytelling. Tension is the thing you want to focus on and storytelling is very common way to create tension. So if ..."
Crafting Effective Titles
In this segment, Dean elaborates on the elements of a compelling title, focusing on mystery, target, and phonetics. He explains how these components work together to draw readers in and ensure they remember the core message of the writing.
"only gave the hook a four out of five, I believe, because the first paragraph didn't really set us up for the core dilemmas that were coming. Now, walk me through a title. Mystery target phonetics. Ri..."
The Art of Sound in Writing
Michael Dean delves into the significance of sound in writing, discussing the roles of repetition, rhythm, and rhyme. He emphasizes the importance of using these elements thoughtfully to enhance the overall composition and impact of the writing.
"mean you can go infinitely deep on any of these patterns, right? Like there's a whole universe in studying phonetics, but the question is what are like what is the the practical basics in terms of how..."
Mastering Your Genre
Dean concludes with a powerful mantra about understanding the fundamentals of one's genre before developing personal taste. He highlights the importance of mastering the basics to create valuable and impactful writing.
"want to do this. I want to go through some maxims and mantras that you have. Okay. And we'll just go one by one. Okay. Sure. Understand the fundamentals of your genre before you develop taste. Yeah. I..."
Establishing Reader Trance
Michael Dean introduces the concept of 'reader trance,' a state where writing captivates the reader so intensely that they cannot put it down. He breaks down the elements that contribute to this trance, including tension, micro-structure, and vivid imagery, emphasizing how these components work together to create an immersive reading experience.
"make this concrete in the world of writing for me. Like what do writers do wrong? Writers think like you sort of had people in the culture, but writers think this when actually you think that. When it..."
AI's Role in Writing
Dean shares his perspective on how AI influences his writing process, emphasizing that while he insists on writing every sentence himself, AI serves as a valuable tool for structural compression and idea generation. He discusses the benefits of using AI for research and how it can spark new ideas, while also acknowledging its limitations in maintaining quality and coherence.
"thing over and over. Yeah, let's do this. The main point of composition is to establish reader trance. So, I feel like reader trance is when the writing is so well done that they're in this state of c..."
The Limitations of AI in Writing
In this segment, Dean explores the inherent limitations of AI in writing, particularly its inability to judge quality and its tendency to produce rapid outputs without self-assessment. He discusses the need for human oversight in writing and the importance of developing a nuanced understanding of writing principles that AI cannot replicate.
"models are you using? What interface are you using for different projects that you're working on? And then how exactly are you actually prompting the models? I'm really interested in the specifics her..."
AI as a Creative Ideation Machine
Michael Dean describes AI as a 'creative ideation machine' that can generate a multitude of possibilities for writers. He explains how using AI can enhance the creative process by exposing writers to a wider range of ideas, ultimately leading to better writing outcomes. Dean emphasizes that while AI can speed up certain tasks, its true value lies in expanding creative horizons.
"are always going to have to do that. If you think about what an LLM is, it has it it has binged trillions of words and it's almost spatially mapping every sentence in some sort of hyper cube, right? S..."
The Case Against ChatGPT in Schools
Dean argues for the necessity of banning ChatGPT in schools to preserve the fundamentals of writing. He believes that the process of writing and editing is crucial for cognitive development and self-exploration. Drawing from his own educational experiences, he illustrates how traditional methods can lead to deeper understanding and mastery of writing skills.
"be. Of course, there are use cases where things can be dramatically faster. But I think if you're working on a piece you care about, you're actually exploring so much surface area that you never would..."
The Future of Writing and AI
In this forward-looking segment, Dean speculates on the future of writing in an AI-dominated landscape. He acknowledges the rapid advancements in AI capabilities while asserting that human writers will always retain a unique advantage. Dean discusses the evolving relationship between AI and writing, suggesting that while AI will play a significant role, the essence of human creativity will remain irreplaceable.
"ideas. And um kids are going to resist this like hell. And I I can give you an example. So I went to architecture school. It's 2009 my freshman year. And uh you know we had software where we could for..."
Quality vs. Quantity in AI Writing
In this segment, Dean argues that while AI may produce an overwhelming volume of writing, the quality could be astonishingly high. He challenges the notion that AI-generated content will be inferior, suggesting that it could redefine standards of excellence in writing. This discussion invites listeners to reconsider their perceptions of creativity and authorship in the age of AI.
"that's the thought experiment. If you're scared about AI as a writer, you say, "Okay, we're not going to quibble with," oh, is this technology there? Is it not there? We're just going to say, "Of cour..."
The Dichotomy of Taste in Art
Dean reflects on the disparity between popular taste and artistic quality, using examples from literature and music. He posits that while AI can produce content that appeals to mass audiences, true artistic merit may still lie in the hands of skilled creators. This segment examines the complexities of audience preferences and the role of AI in shaping cultural consumption.
"be unimaginably good. It could get to a point where it's not that it writes better than us. It's not that it writes better than the the best living writers. It will be extraterrestrially good, right? ..."
AI's Role in New Creative Forms
This segment explores how AI could lead to the emergence of new forms of writing and art. Dean discusses the concept of collective creativity, where AI synthesizes diverse voices into cohesive works. He emphasizes the potential for AI to innovate in ways that were previously unimaginable, challenging traditional notions of authorship and collaboration.
"so to me that study on AI slop is kind of irrelevant to me cuz I don't even know who the readers are, right? You know, so I'm not so indexed on math taste. I'm really chasing like what is beauty? What..."
Personal Writing in the Age of AI
Dean shares his approach to personal writing, emphasizing the importance of documenting one's experiences and memories. He argues that by making personal narratives machine-readable, individuals can create AI replicas that reflect their unique perspectives. This segment highlights the intersection of personal storytelling and technology, advocating for the value of individual voices in a digital landscape.
"there that we haven't spoken about is new forms that are birthed by AI. I mean, this is just what we see all the time. What new technology does is it takes certain things that have always been true th..."
The Writer's Apocalypse: Embracing Change
In this thought-provoking segment, Dean addresses the concept of the 'writer's apocalypse' in the context of AI advancements. He discusses his acceptance of AI's potential to surpass human writing and how it motivates him to continue creating. This segment encourages writers to adapt and find meaning in their craft, regardless of technological disruptions.
"It's just I mean there's that and I think you also said oh it'll be eight out of 10. Like I think it could be like 50 out of 10. Like I don't think there's a limit to AI producing the funniest thing y..."
Leveraging AI for Personal Growth
Dean concludes by discussing the transformative potential of AI in personal writing. He envisions a future where individuals can leverage AI to enhance their creative processes and articulate their thoughts more effectively. This segment emphasizes the importance of continuous writing and self-reflection in a rapidly evolving technological landscape.
"focus on some technical limitation be like well it's never possible because of this and so therefore humans will always do that. But what I'd say is that I think people are locked into thinking about ..."
The Writer's Apocalypse: Embracing AI
Michael Dean discusses the impact of AI on writing and why he remains optimistic despite fears of a 'writer's apocalypse.' He explores the idea of using AI as a tool to enhance the writing process, allowing for greater productivity and clarity in thought. Dean emphasizes that his passion for writing stems from a desire to understand and document his experiences, regardless of technological advancements.
"and also your own personal experiences, feelings and memories too. Like the more of yourself you can make machine legible, the more you're able to have a thing that you can work with that is like a mi..."
Writing as a Linguistic Puzzle
In this segment, Dean reflects on the joy of writing as a process of clarifying thoughts and ideas. He explains how writing transforms fuzzy concepts into clear, educational, and entertaining narratives. Dean highlights the importance of writing for self-discovery and communication, asserting that even with AI assistance, the essence of writing remains a personal journey.
"me let me always kind of remember the core reason why I do it and no matter what gets disrupted in the outer world, I'll figure out how I can plug into it and I'll keep doing this. So there's a world ..."
AI as a Writing Coach
Michael Dean shares his vision of AI as a supportive writing coach that can help writers identify their strengths and weaknesses. He discusses how AI can accelerate the learning process in writing, making it more accessible and personalized. Dean believes that this technology can enhance the writing experience without replacing the fundamental act of writing itself.
"affect you. Yeah. Because I'm not really interested in AI doing the writing or thinking for me. That's not really fun. I'm I'm I'm interested in finding the truth and writing something of quality. And..."
The Future of Writing Education
In this concluding segment, Dean outlines his thesis that writing quality is objective and can be measured through a systematic framework. He envisions a future where writing education is self-driven, utilizing AI to provide tailored feedback and support. Dean emphasizes the importance of mastering writing as a fundamental skill that can be enhanced through technology, ultimately fostering a new generation of well-rounded writers.
"companion that knows you intimately. Right. Yeah. So I I think education has been this mode of mass dissemination where every kid learns the same thing at the same rates and I think curriculums of the..."