• I was on the How I Write podcast with David Perell. We deconstructed two essays (Consider the Lobster by David Foster Wallace and Shooting an Elephant by George Orwell) and got into process/technology. Link and timestamps below.

• essayarchitecture.com is live! Enter your email there if you’re interested in more frequent product updates (starting soon). There’s also a form to join the beta and try it early. Thanks for your patience if you’re on the waitlist. I’m onboarding writers one at a time, and attempting to make meaningful updates between sessions.

• Upcoming essays:

  • “The Babbling Idiot and the Tribe.” This one is a Response to Food of the Gods, the book where Terence McKenna popularized the Stone Ape Theory. Did psychedelic mushrooms played a role in human evolution?

  • “45 predictions on writing in 2045.” Pretty self-explanatory. The goal of this thought experiment is to map out how weird the future of writing might get and to find my place in it. The good news is that I think the timeless reasons to write hold up, and even evolve in some positive ways.

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• Logs: March and April were intense for me, and I feel guilty for not sharing as much as I planned on, but I still managed to publish 25k words without realizing. Here are my logs for March (locked), April (open), and May (in progress). This is a reminder that, if you’re low on time, you can lower the scope to a single paragraph, and put any mild epiphanies you have into words.

How I Write:

Episode Link

Introduction

• Opening (0:00)

• Is writing quality objective or subjective? (0:41)

• How architects use diagrams to see patterns (6:26)

Deconstructing two classic essays

• The Pick One Volcano principle (to limit your scope) (10:16)

• Paragraphs are the atomic unit of composition (13:06)

• Deconstructing the maximalism of David Foster Wallace (18:24)

• Personal experience = biography + interiority + outlook (22:35)

• Conflict = Intention + Obstacle + Consequence (29:33)

• How to organize an essay around invisible questions (33:18)

• Good hooks have questions in the subtext (38:25)

• On sound and rhyme in prose (41:01)

On process (reading, writing, editing)

• Balancing intuition and analysis (44:02)

• Using editing lenses to isolate patterns (51:29)

• Why is voice important? (53:12)

• Capturing your consciousness on the page (54:15)

• Privacy can unlock writing voice (57:59)

• How to ask for feedback (59:50)

• How to read analytically (1:01:38)

A Pattern Language

• A pattern language is a hierarchical network of constraints (1:02:25)

• Essays let you become a writing generalist (1:04:49)

• Storytelling is stretching the unknown across time (1:06:38)

• On titles and the way they sound (1:07:42)

• Repetition, rhythm, rhyme (1:10:04)

• Word choice is negotiation between concision, precision, invention (1:11:40)

• What causes reader’s trance? (1:15:05)

AI, Education, & the Future

• AI for compression, research, word choice (1:17:04)

• Limitations of AI for writing and editing (1:20:18)

• On banning ChatGPT in schools (1:24:54)

• On adapting to the rate of AI progress (1:27:38)

• On personalizing AI by writing your memories (1:37:42)

• Will you still write if AI gets phenomenal at writing? (1:41:46)

• On building tools for teaching composition (1:46:06)

Questions:

If essay means “to try,” then a draft is the trial of a fuzzy question in your head. A draft isn’t your final answer, but your attempt to formulate a more specific question. If you have clarity on the question you're asking, the essay usually comes out a lot easier. In that spirit, I’m using this space to frame some recent thoughts as questions. This is an invitation for you to share your own answers (either leave a comment, or use these as prompts for essays of your own).

q1. (rationality):

Why does popular creativity advice downplay the value of technique?

The spirit of Essay Architecture runs counter to the spirit of our times. It feels like everything runs on vibes. Maybe it’s dramatic to call our moment a “revolt against reason,” but it seems many writers believe the mind is detrimental to making things. Is all thinking overthinking? It’s increasingly popular to justify anything you do with your taste or intuition—to celebrate laziness, cheating, slop, and sloppiness. Typos are in. Effort is mocked.

It’s probably fair to call Rick Rubin our leading figurehead in non-rational creativity. There’s much I respect about A Creative Act (2023)—I think psychological attunement is real—I just think it’s a bad starting point for beginners. Rubin is famous for unlocking artists who were a decade or more into their journey. Surrendering your ego makes a lot of sense if you are post-peak Johnny Cash. But if you’re not fluent in your medium yet, it might be better to focus on discipline and craft instead of “being open to the world to make something you love.” Learn the scales!

I’ve been wondering when, how, and why non-rational creativity became so popular. The best selling book in this genre is The Artists Way (1992) by Julia Cameron. She de-emphasizes the role of technique; instead she wants you to dissolve resistance, experiment, and heal emotionally. She’s most known for “morning pages,” where you dump three pages into a journal each morning and never read it again. She sold five million copies. How pivotal was this in framing creativity as a type of therapy?

I think we should fuse the psychological and the technical—the problem is that the technical realities of an art are hard enough to dissuade beginners. Consider the accessibility of Rubin’s “I just know what I like” compared to Christopher Alexander’s language of 253 patterns. A consequence of democratizing creativity is that we may have inadvertently sterilized our technical creative knowledge. There will always be 100x more beginners than practicing artists, and so it’s far more profitable to share “how to start” than “how to actually do the thing.”

If you have any thoughts on these dynamics, let me know. I wonder if it’s as simple as this: writers justify an avoidance of editing because it’s hard. In addition to building a tool that makes editing approachable, I probably also need to recast a new myth to make editing emotionally and psychologically approachable (a v2 of alchemy of the rewrite). There’s joy in doing hard things.

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q2. (destruction):

When is it worth starting over from scratch?

To make something great—an essay, a song, a building, software, anything—it often helps to destroy the design concept and start over, possibly multiple times. Rewriting is underrated. I won’t expand on all the reasons why we avoid it (ego, impatience, the sunk-cost fallacy, the secret hope that this draft is the draft); instead, I’m wondering when it’s actually worth it. You can’t rewrite everything. If you did, every idea would be in permanent limbo. Most ideas are probably fine sharing at 80% of their potential—my logs are maybe at 5%—but there are a few occasions where perfectionism is worth it.

This is relevant to me now because I’m doing a full rebuild on significant parts of my app (on v3 now). After evolving this over 25 interviews, the UX is getting much smoother, but I’m haunted by what might be a limit in suggestion precision. My problem is that I’ve been training it to be an expert analyst, not an expert editor. So even though I’m close to my goal of +90% accuracy in how it evaluates each pattern, and even though it organizes all your scores into a sleek interactive spider graph, its advice on how to improve is only slightly better than a chatbot. Right now, it can’t match the granularity of how I personally give feedback (“you’re doing something similar in p(6) and p(13), what if you combine those, move it up to p(2) and expand on X to achieve Y?”). It makes me wonder—could I rebuild the analysis engine with the main goal of giving great feedback?

For this to work, I need to get absurdly granular. I already have a detailed scoring system (with 81 criteria), but it currently only understands your draft as a single monolithic object. Essays have sub-objects right? They have sections, paragraphs, sentences, and words. If I want paragraph-level suggestions, then I need paragraph-level analysis. If I want to match the intuition of a great human editor, maybe each draft you upload needs to run 5,000 micro-prompts. This feels right, but sounds technically impossible.

But the beauty of starting over is that 1) you understand the problem 10x better, and 2) the context around you is different. I’ve been playing with some new models that are less than a month old, and I’m realizing that I can feed in an array of paragraphs and run hundreds of precise mini-evaluations, all through a single API call. Not only will the suggestions be better, but the whole thing might be cheaper and faster too.

So when is it worth starting over? Maybe: 1) if it has high relative importance compared to your other projects, 2) if the sphere of improvement matters (ie: are you fixing the main thing or a frilly detail?), and 3) if the time it takes to rebuild is small compared to the time the new thing will be useful for (ie: a 2-month delay is okay if the new thing sticks around for 2 years). Any other heuristics?

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q3. (disobedience):

Do you want technology to agree with you or challenge you?

When people ask me, “why would I use your app over ChatGPT to get feedback?” I point them to the latest dilemma with 4o. Last week, OpenAI had to rollback their latest 4o model because it was too sycophantic. It’s too obedient. It’s too willing to tell users exactly what they want to hear. There are many screenshots online of ChatGPT calling its user a gifted genius. You can probably guess why this makes it a bad editor: it’s incentivized to not challenge you.

During my 1:1 beta calls, I’ve noticed a few writers score low on a pattern and say, “That makes sense because I wasn’t really going for that.” Maybe a memoirist doesn’t care about the Argument pattern, or an intellectual doesn’t care for Experience or Tone. If I were to follow the best practices of product design, I’d understand what each writer wants and give them exactly that. The more I think about it though, the more I realized that the goal of Essay Architecture is to help you expand your conception of what an essay can be.

This got me to realize that product maxims for an educational tool might be very different from SaaS or content marketing. If you’re building a writing tool and you listen to the average user, you will likely end up with an advanced auto-complete that provides and implements all your edits in a single click. No writing necessary! Earlier this year I published Thank you for the roses, about how TikTok creators devolve into insanity when they optimize for market signals. The Internet enables everyone to get high-volume real-time metrics, and there's a risk in watering down your vision to become a mirror to the market.

If the default is for every app to conform to its user, maybe it’s refreshing to have an editing app that has a single quality standard that applies to everyone? The risk here is obvious. The tool won’t bend to make you immediately happy. It’s disobedient—but good teachers challenge you. Learning involves shedding old models to build new ones, and that initial clash could be enough to scare someone away.

Maybe there’s a way to fuse validation with abrasiveness. For example, good feedback starts by acknowledging the writer’s vision before pushing them further: “You’ve done great with patterns A, B, and C, but you seem to ignore patterns X, Y, and Z, and maybe you think those two sets don’t typically go together, but here’s a link to a classic essay that shows all these patterns working together in a single piece.”

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Productive Friction

The shared theme among all 3 questions is the value of “productive friction.” It’s easier to run on vibes than to practice technique. It’s easier to stop at 80% than to start over. It’s easier to build something people want than to build something people need. It makes sense that a technology-obsessed culture strives to eliminate all friction, but a creative practice isn’t forged from inspiration, comfort, or validation—but how you evolve under pressure.

What do you think?

• Why does popular creativity advice downplay the value of technique?

• When is it worth starting over from scratch?

• Do you want technology to agree with you or challenge you?

Welcome to Essay Architecture. If you’re new to this Substack, you might want to start with A Pattern Language. Today I’m sharing a short essay to introduce a new experiment (I’m livestreaming Friday at 9AM). At the bottom you’ll find updates on the essay analysis software I’m building, and some links to recent writing.

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Wordcels are the least likely breed to show their face on camera, and so it’s ironic that Substack is trying to turn its writers into streamers. I got an email this week: “Launch your own live video show on Substack.” The last year has seen a dizzying array of video tools (podcasts, clips, transcriptions, livestreams, etc.) and so at the bottom of any of these feature updates you’ll find a grumbling cohort of prose-only creators.

Substack is putting in a lot of effort to help you build a multimedia empire, but most of us just want to keep our blog alive. Are they betraying their core user? Personally I’m not so grumpy about video. I’m keen to experiment. Even if it brings an influx of TikTokers, I'm confident Substack won’t turn into an NPC hellhole. Still, this place was founded by writers, and so I’ve been wondering—how might writers hijack video?

They could aim their phone at their monitor and just stream themselves drafting in Google Docs with size 36 font. For a delusional moment, I imagined this could be a symbolic way for writers to take back their medium—at 5pm ET tomorrow, we’ll all live-write at the same time and crash the app—but then I remembered that writing is incredibly boring to watch.

Writing is mostly pausing, thinking, editing, deleting, procrastinating, and starting over. In Essay Writing as Personal Sovereignty, I shared that it took me 45 hours to write a 2,700 word essay. This comes out to 1 word per minute (wpm). If writing wanted to resemble a live performance, a writer would have to write as fast as a reader reads: +200 wpm. The average writer types at 40 wpm. This 5x difference explains why live writing isn’t a genre. Our fingers are the bottleneck. But what if I trained to be a competitive typist?

When I was in elementary school I’d hang out in the computer lab and spend hours doing free typing tests for fun. This might be a false memory, but I remember cracking 200 wpm as a 5th grader. I took one now and only got 124 wpm. I’m rusty. Worth noting, this is not the speed of thinking, but the speed of mindlessly typing over random sentences—you’re so indexed on speed that it might say, “the quick brown fox jumped over the lazy dog and fucked a pig,” and you wouldn’t notice.1

So two Fridays ago I streamed on Substack. I bought a $17 mount from Amazon to position my phone camera. I set my font to 3x. The “moire effect” distortion is part of the charm. I said I’d only try it for 15 minutes, but ended up going for 50 and almost missed my train (on Valentine’s Day). In that time I wrote 2,700 words (!) which comes out to an average of 54 wpm. I took some short breaks to prevent wrist failure, and so I imagine the general sustained pace was more like 80-100 wpm. Even if that’s 2x slower than skim-reading, it’s 50x faster than how I usually write. This is by no means a come-behind-the-scenes-to-watch-how-I-actually-write experience. This is a social experiment to shock me out of editor-brain.

Maybe you’ve heard of “The Most Dangerous Writing App,” a clever tool to get writers out of their head. You set a timer (10 minutes) and your text starts to fade red when you stop typing. If you stop for 5 seconds, the whole document deletes itself. I’ve done this dozens of times to get an initial draft on the page, and I found that live writing to 38 people on Substack Live is more intense. I’d rather lose all my work than expose myself as a fraud who can’t write. Writing, live and unedited, is something like streaking. You’re naked but moving fast enough to blur the parts. It’s liberating, but likely annoying.

Did anyone enjoy my stream? I’m not sure if 38 people stuck around for every sentence or if 300 people cycled in and out for the spectacle. I only got two pieces of feedback: one said, “I’ve never seen anyone do that before,” and another said “good ASMR content” (meaning you can get off to the sound of my mechanical keyboard without even having to read).

Maybe the important question here: did I enjoy doing it?

I experienced a flow state unlike anything I’ve ever felt. Like a roller coaster, I almost vomited and I’m ready to go again. I wasn’t queasy from nerves. I got queasy from concentrating so hard that I didn’t blink for 10 minutes. Writing at high speed means you have to simultaneously map out the next sentence while you chisel the one you’re on. It’s a 100% bandwidth kind of activity. The critical difference between this and stream of consciousness drafting is the live audience. It’s a performance. When you realize there’s zero lag between a keystroke and the stranger reading it, you tap into Jack Kerouac mode, but without the amphetamines.

There are some obvious reasons why speed writing in public is a bad idea:

1. Truman Capote criticized Kerouac by saying, “that’s not writing, that’s typing.” If you don’t stop and recursively loop thought back on itself, there’s a limit to the density and elegance of your prose. On the Road was an untouchable heap until Malcolm Cowley edited it. You might even say a core reason why LLMs suck at writing (for now) is because they write way too fast. They can’t pause to re-evaluate the prompt, context or outputs. Once they’ve mathematically matched your question with the trillions of words they’ve guzzled, they can only barrel forward, blindly.

2. Now, amplify the perils of speed with misaligned social incentives: do I go more viral if I let the crowd control me? Is this some kind of literary AMA where the audience sets the topic for the next paragraph? Is it worth being the inventor of MMCCP (massively multiplayer crowd-controlled prose)? If I hack Substack Live and go wildly viral and have thousands of new viewers per day—will this encourages me to speed write at 100 wpm for 6 hours a day w/o break like a high-brow Pinkydoll? How long until my wrists permanently conk?

Risk aside, I’d like to find the sweet spot with speedwriting because it’s the perfect counterpoint to Essay Architecture. My main project is basically an editing philosophy. It’s slow. It’s cerebral. It runs counter to the aesthetic of speed that’s blooming on Substack. I see more and more Notes about not re-reading your work, keeping the typos, and letting essays spiral in random directions. Speed might make a terrible main-mode, but a terrific sub-mode: it’s a specific way to practice. If you want to get good at any game, you need to find enjoyable sub-games to isolate skills. I find the more contradictory the sub-games, the better. Sometimes I publish logs to my website w/o re-reading them; sometimes I gather 20 beta-readers and spend 100+ hours editing. Sometimes I’ll take 3 hours to score a classic essay on a 405-point rubric; and sometimes I livestream at 54 wpm without a plan.

The strictly slow get constipated with theory. The strictly fast can never give form to verbal diarrhea. But when you shift from slow to fast, you turn abstract concepts into embodied knowledge.

The goal of Essay Architecture isn’t to cram your head with rules, it’s to forget them. The more you train, the more coherent the improv.

A big and possibly unexpected influence of mine is the Grateful Dead. If you asked Rick Rubin why they’re so good, he’d say, “They trust their intuition, embrace imperfection, pay attention, and chase real moments.” All true. But they can only operate in their realm of creative ooze because they were so disciplined when they started. Jerry Garcia was a competition banjo player who practiced scales 10+ hours a day. Phil was classically trained. Mickey wrote a book on rhythm. The early Dead even kicked out young Bob Weir because he didn’t practice hard enough—he had to work his way back into the band. Years of study will shape your intuition so that you can eventually operate with your mind almost completely off. You get out of your head by training your head. Even Kerouac wrote a million words of traditional novels over 10 years before he dared write On the Road.

Updates:

Livestreaming on Friday at 9am ET.

I’ll be on at 9am ET tomorrow, and from then on, who knows. I think I’m going to riff on “Writing in 2045,” but anything could happen. To start, I want to keep this experiment as loose as possible. Substack is encouraging “live shows” (ie: watch me riff every Friday at Xpm ET). I’d rather it be unannounced, at random hours, hopefully multiple times per day, sometimes 15 minutes, sometimes 2 hours, sometimes NPC mode, sometimes in control.

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Want to try the Essay Architecture app?

I still have another few months of polish, refinement, and testing before I launch this in full, but I want to start onboarding writers now. The core flow works. You upload a draft and it runs 120 prompts over it, finds your blindspots, and then orients you into a 42,000 word wiki. My plan is to onboard writers 1:1 over Zoom. We’ll upload your draft, walk through the app together, find UX hiccups, and talk big picture around the features you need. I’ll give you some free credits so you can continue using it after our call. In these early days, I’ll grow the user base as slowly as possible. I’ll onboard 1-2 writers per day and rapidly implement their best suggestions for the next day’s onboarding. If you want to help shape this, the button below leads you to a form with ~10 questions. From there I’ll follow up with a Calendly link sometime in the next few weeks.

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Published since last update

This is my 4th post here in ~50 days, which is close to my 3x a month goal for 2025. I’ll be publishing a few more times here in the next week to meet my February goals. Essay Club is helping me with my own practice, and our group’s publishing rate in January was 67% (pretty good, considering how hard it is to stay consistent). If you want to start a long-term writing habit, check it out or send me a message.

• Year of the wiki (about the essay app I’m building)

• Best American Essays? (a review of the 2024 essay anthology)

• Thank you for the roses (a long form essay about NPC streamers on TikTok)

• Logloglog (155 notes from January 2025) 🔒

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Footnotes:

January is a natural time to celebrate all that’s working and to let die whatever isn’t. To me, it’s less about looking backwards or forwards and more about ruthlessly pruning. After all, it’s a new year, and the origin of the word resolution1 means “to release.” It’s a time to audit and purge the physical and mental, the small and big. And so in the last week I donated books and clothes, nuked the fridge, emptied whole drawers of forgotten sundries,2 unpinned uninspiring posters, and—after much needles toil—decided:

“Essay Architecture doesn’t need to exist as a book, actually.”

I conceived this project in November of 2023, and the idea was to release one chapter at a time on Substack until I had the material for a physical book (which at one point I joked would be so fat that it would be a cube). I’m proud of the 14 Essay Architecture posts I shared in 2024, but this process isn’t suited for what’s ahead. I need to molt3 (again).

Ultimately, my problem: I had a linear process for a non-linear project.4 I went through my 27 patterns, one-by-one, and turned each one into a polished, illustrated, longform essay. This should have been suspicious to me: I wouldn’t want readers to read the finished book chapter-by-chapter, so why should my process be so linear? The omega point of Essay Architecture is to create a history-infused draft analyzer that finds your compositional blindspots and points you to specific chapters (“Nice essay, you’re doing great with X, Y, Z, but you should check out Chapters 3, 5, and 17 to improve your…”).

I still recommend my chapters on thesis, microcosm, response, catalyst, and material, but the mode of turning research into prose is very different from what’s required to make an actually good AI feedback app (one that doesn’t bullshit you). No matter how hard I work, I can’t make a great app and a great book. I need to make an app that is a book. (Not a book that is an app—big difference.5)

So the book isn’t dead; I now get to re-imagine what a digital (text)book can be. How would Christopher Alexander release A Pattern Language in 2025? What format can a non-linear always-evolving corpus of ideas take? What would let me publish a v1 of all 40 chapters by February 1st?

The answer to these three questions is the same: an essay wiki. First I’ll share why I think this format best captures the spirit of the project, and then I’ll get into what you might expect from this Substack moving forward.

The Essay Architecture framework is already wikiesque_

A pattern language has two modes of organization: hierarchy and associations. A wiki captures both. The hierarchy locates a concept in the framework, the associations link it to related concepts. For example, the Image pattern is located under Voice/Sight(9)/Image(9.1), and if you want to know the other patterns that image-making is linked to, you might want to check out Microcosm (2.1), Title/Mystery (3.1), Hook (4.3), Paragraph/Finale (6.3), Motif (9.3), etc.

I could write 5,000 words of prose about imagery, but the inherent linearity of an essay clashes with the curiosity of a self-directed learner. While prose is best at conveying a single arc, it’s not great at conveying complex maps. The only way to learn a hyperobject6 is to burrow through it. A wiki lets you locate, skim, zoom into, and link out to related ideas. The ultimate affirmation here is that Christopher Alexander—the architect who wrote A Pattern Language in 1978, and a big influence on this project—was a direct inspiration to the inventor of the wiki in 1994.7

So the plan now is to build a wiki directly into this app.8 You upload your draft, wait ~3 minutes, and get a feedback report—it gives you insights into your strengths and weaknesses, and each hyperlinked term is a portal into the wikiverse. This switches learning from a push to a pull model: you don’t have to trek through a textbook and cram concepts; instead, the right theory wraps itself around you at the right time.

AI isn’t writing your sentences, AI is the bridge between your shitty first draft and a human-created network of composition theory.

The wiki format also makes the project faster, flexible, collaborative, and sustainable. Unlike essays (which are like tightly-wound puzzles of prose), a wiki page is made of modules that exist in an outline. There doesn’t need to be a final/ultimate order. Over months and years, I can add/edit/arrange/delete. Now the project feels like an infinite game. It’s rejuvenating. I’m on track to release a v1 of all the core pages in February. From there, I hope it evolves into an online home for essayists to learn from and contribute to.

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What to expect from this Substack in 2025_

• Monthly updates: I’ll send updates like this near the beginning of each month. As the project evolves I imagine I’ll share links, forms, videos, the challenges of building something, etc. I’ll also curate any new writings or wikis.

• Essay Architecture posts: The goal here is to send one post a month for paid subscribers. These might take the form of essay reviews, pattern deep-dives, visual breakdowns, or something unpredictable (I want to break from linear chapters, and instead share something I’m actively studying).

• Longform essays: I have three of these that are nearly finished, and hope to ship them monthly. Even though the title of this thing is Essay Architecture, it’s important to me that I ship essays on completely random topics (Apple Vision Pro, human evolution, NPC streamers on TikTok, etc.). By escaping the meta-project and sharing my own essays on anything I feel like, I stay grounded in the process and can speak to it better.

• Essay Club: Last October I started a publishing accountability group on my Founding Members tier. Every month we set a goal, have 6-7 feedback exchanges on Zoom, and then publish by the 1st. I track and share streaks, so if you miss, you restart at 0. If you want to build a longterm writing habit, check it out. I felt compelled to start this after the closing of Write of Passage (the writing course I took in 2020 and have worked closely with since). It’s worth noting, I’m a member of Essay Club too. I have ambitious publishing goals9 and I see this group as a forcing function to make it possible.

• Substack Chat: I just launched this yesterday and want to experiment with it this year. The settings are somewhat cryptic, so I apologize if you get bombed with notifications (you can change these in your app settings). Two goals here: 1) to share emerging ideas, research, and questions around Essay Architecture, and 2) to create a place for Essay Club to chat & share drafts.

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Thanks for reading! I’m aiming to send two more posts this month: one is a review of the 2024 edition of the Best American Essays series, the other is a long-overdue account of my 10 days with the Apple Visio Pro. Until then, say hey in the comments or in the chat (let’s talk wikis).

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Footnotes:

These are ideas that were either (a) originally in the essay but edited out, or (b) triggered in the flow of writing—they seemed too tangential to include, but interesting enough to want to write out after. This is something like a graveyard of thoughts that didn’t make the cut.

I first saw “ur” used as an adjective in a Lawrence Ferlinghetti poem1; it’s a German word for “archetypal,”2 but it also reminds me of the place. Ur was an ancient Sumerian city, the original city, the city that went on to shape all cities.3 It was where all the components of a civilization first intertwined: architecture, law, math, writing, religion, economics. It was a full-stack city.

I’d define an “Ur pattern,” then, as a stack of ancient components; they form an archetype that shapes every instance in a genre, even if we don’t easily recognize it.

“... And if you find it, it’s the mother lode.”4

Earlier this year I applied for an O’Shaughnessy Fellowship grant. The chances were something like 1 in 500, and although it may sound unlikely that a company with roots in quantitative asset management would invest in a writing textbook, I sensed there was a parallel. The opening line of my application—under the “unique insight” section—was a claim that is unorthodox in the writing community:

“Quality isn’t subjective, it’s statistical.”

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Turning the Ur pattern into code_

For half-a-millennia, the medium of the essay has evaded classification, measure, and standards. This creates in-fighting and needless confusion, especially for new writers looking to learn.

I’m reading a book called Essayists on the Essay, which curates a 450-year async debate on WTF an essay even is, from Montaigne to Paul Graham. The opening line says, “the essay has yet to find its Aristotle.” It’s a mystery that no one has mapped the medium. The discord is clear in how Phillip Lopate—known for the “personal” essay—excluded Emerson and Bacon from his anthology. Some writers claim that their type of writing is all that matters. Other writers insist that essays are meandering streams of thought, allergic to rules.

Despite the radical range of essay types, and despite the wrinkles through history, culture, and readers, I sense there’s an Ur pattern under everything. Well, where does it come from? Why does it exist? You can find similar moves across all essays, not because of influence, but because every reader is human.

We all have limited bandwidth, we all read text linearly, and we all (generally) process reality through sight, sound, and emotion.5 Our neuropsychology matters; it invisibly shapes our constraints.

My goal is to unify the scattered schools of thought under a shared rubric.

I believe the essay is a unifier of opposites. An essay can be confessional and persuasive. An essay can be academic and psychedelic. It encompasses all corners of the human psyche. Whichever “type” of essay, it can be analyzed along a shared set of patterns.6

Quality is elegance across many patterns (more patterns than the mind can consciously hold at once). 

This system is paradoxically objective and subjective. The Ur pattern is the universal archetype under everything, and your essay is a unique instance. It is an original work on ancient scaffolding.

None of these patterns are “new,” but no one has 1) assembled them into an hierarchical framework, 2) insisted that each one holds equal importance, and 3) created a scoring criteria so each one can be measured.

The real question: what is the best way to teach this? By next year I’ll have a 500 page textbook, but surely the best way to learn isn’t by cramming your head with rules. You learn by isolating one pattern at a time and practicing it through editing until it becomes second-nature.

But which pattern do you start with? (And how well can you articulate your own writing weaknesses?)

If there is an Ur pattern below the galaxaic range of essays, and if it were machine-readable, then any writer could use software to see their strengths and weaknesses. It would read your drafts and point you to the lessons you need to learn. This would give writers a path to bring their ideas to maximum, historic potency.

I applied for the O’Shaughnessy Fellowship, not just to finish my textbook, but to turn my philosophy of writing into code, and to elevate the quality of essays across the Internet. I heard back recently, and have an exciting update to share:

I won an O’Shaughnessy Fellowship Grant!_

I’m thrilled for this opportunity: it fuses the past threads of my life (architecture, technology, and writing), and it gives me the clarity, guidance, and resources to bring Essay Architecture into its fullest form. 

Since 2020, my main goal has been—and still is—to master the essay. This next year I’ll dive deeper into the craft than I ever have, and distill what I learn into a product to help other writers. I’ve edited and coached and built courses before, but this can scale who I can help (if you’re one of the few who half-jokingly pitched that I turn myself into code, well then good news: Deanbot is happening).

What I’m building is quite different from the other AI writing apps you’ve tried. It’s not a chatbot. It’s not about automating your process, but guiding you on a life-long one. I’d rather alchemize minds than automate words. Jim made an elegant distinction in last Friday’s press release on the difference between AI doing the writing and AI helping the writer:

"Despite the influx of new and exciting technologies, writing—one of our oldest technologies—has remained as central to our civilization as ever, and while AI alone will never fulfill our need for great writing, it has the potential to be an incredibly valuable tool for the writers of the future.”

My product won’t write sentences for you. The slow process of writing is what clarifies thought, shapes identity, and cultivates a lens to the world. Writing is the whole point; it isn’t a chore to optimize, it’s an infinite game. 

What I’m building is more like an editor turned into software. Think of it like Grammarly, but instead of neutering your prose through line-edits, it asks you profound questions that help you formulate Draft #2.

I want to give you a high-resolution mirror into your craft and draft. Imagine getting instant and thorough reports through a gDoc plug-in. Not only will it give you big picture feedback, but it’ll score your writing 1-5 across all 27 patterns. By clicking into a point, you’ll find paragraphs of feedback, examples, questions, resources, and exercises.

I’ve made a few of these reports for friends, manually. They take a few hours to make, and usually they’re 3x longer than the essay itself. People say it gives them clarity around the writing snags they’ve felt, but could never see or articulate. A year from now, I want to make this available to everybody in a single click.

The core technical challenge is making an AI editor reliable. Even though GPT-4o has binged trillions of words, it doesn’t inherently know the Ur pattern. As you probably know by now, AI will sometimes give you boondoggle.7 Even though ChatGPT can share feedback on your drafts—and is great for rubberducking8—it’s not exactly consistent (when I ask it to score essays, it acts like a random number generator).

Is it possible for AI to score essays as accurately as I do?

The only way to know is through benchmarking: if I manually scored 200 essays out of 135 points and then tested AI against my control set, I could see precisely how wrong it is. My manual score set is the north star for my AI development.

I’ll keep iterating through different methods—prompts, transformations, fine-tuning, syntax stats, etc.—to close the gap between my scores and machine scores.

This means I’m going to be reading a lot of essays, and that leads to the next announcement:

My list of scored essays is public_

This year I’ve been making monthly trips to The Strand Bookstore to build my collection of essay books. I try to read and score one every day. Each one gets graded out of 135 points. It’s manual, but enjoyable, and it also powers the whole project. My reading habit will lead me to a dataset of 5,400 points that I’ll use to interrogate a LLM.

It’ll take some time to get the AI scoring accurately, but in the meantime I’ll be sharing the essays I read here.

Currently the list has 37 essays with links to the URL. In some cases, it includes a link to buy the essay book on Amazon. Expect this to keep growing every week. For now, everything is manually scored, but once my AI is reliable, this can rapidly grow to include thousands—heck, millions?—of essays.

As you’ll notice, everything is scored out of 10; this score is a proxy for “formal completeness.”

It doesn’t matter how much I like the subject matter.

It doesn’t matter how famous the author is.

This system is blind to history, culture, and politics. It measures how well the essay scores on the Essay Architecture framework. Each pattern has equal weight. So many of the essays I’ve read excel in one dimension, but neglect others. It’s easy for a reader to get excited over a flash of brilliance, but as writers we want to know the consequence of each weakness.

This list is more a measure of well-roundedness than mono-dimensional power.

I sense that school has programmed our culture to get queasy around grades, and also to see anything south of 9 as some type of failure. In this system, anything above a 5.5 (3 out of 5) is a win and makes the list. Anything above 7.8 (4 out of 5) is great.

I know these scores alone don’t reveal much (why is Self-Reliance an 8.4?), so that’s why twice a month I’ll release detailed essay Reviews. You’ll see the score report, along with insights on how it’s working in each dimension. For the first one, I’ll be reviewing Susan Sontag’s “Against Interpretation.”

Based on the title, I went in thinking she’d oppose my whole project, but it turns out we’re on the same page:

“What kind of criticism, of commentary on the arts, is desirable today? … What is needed, first, is more attention to form in art. If excessive stress on content provokes the arrogance of interpretation, more … thorough descriptions of form would silence. … What is needed is a vocabulary—a descriptive, rather than prescriptive, vocabulary—for forms.” —Susan Sontag, 1964.

Scoring systems usually have an agenda of harvesting attention through acerbic teardowns. That’s not the point here. The purpose of this list is to, 1) give you a reading list of inspiring essays, 2) teach you writing patterns through in-depth reviews, and 3) ground my analysis tool.

For the last year and a half, this newsletter has been called “Dean’s List,” but I think this name is better suited for my mega-list of scored essays. So, here’s the last update for today:

This newsletter is now called Essay Architecture_

Given my focus is to release a textbook and a tool, I figured I’d align my Substack’s name with that mission. That said, I still see Substack as the home for all of my creative projects.

I’ve set up sections so you can customize what you get in your inbox (sections: Essays, Chapters, Reviews, Experiments, Updates). At any time, you can update this in your account settings.

Here’s a reminder of what subscribers get each month.

All subscribers get:

• A monthly essay, covering an eclectic range of topics, like the influence of American Idol on social media architecture, the role of psychedelics in ancient Greek religions, the nature of Beatles fan-fiction post-singularity, a biography of an online writer from 1994, and thoughts on Leap Year.

• 2 essay reviews per month, curated from Dean’s List, where I score and break down essays across history.

• Previews of my textbook Essay Architecture. Once a month you get a full chapter that overviews 3 patterns (like this). While pattern posts are for paid subscribers, you’ll still get a helpful preview of each one.

• A monthly update, aggregating links of my latest posts.

Paid subscribers will get:

• All chapters of Essay Architecture—sent weekly—including visuals, examples, and prompts. Check out the 3 chapters within Thesis: Microcosm, Response, Catalyst.

• A look behind the scenes, including typewriter drafts and the full archive of daily logs.

• As I develop my AI editor, I’ll share beta releases with paid subscribers.

• Founding members get access to The Writing Studio, a community of writers that meet twice a week to exchange drafts for feedback.

Here are some essays I’ve posted since last update:

• The alchemy of the rewrite (on “essay” vs. “assay”)

• A 10% compression cover of Emerson’s Self-Reliance

• A case for cassette tapes over Otter for voice recordings ($)

• On finding the journal of my 12th-grade pre-writer self ($)

• Kairos: on sneaking into baseball games ($)

And also, I went through and tagged all of my old posts. Now you have a tag cloud to visualize the multiple rabbit holes that exist on my site. Enjoy!

FEATURED : #2024, #alchemy, #altered states, #analog, #antiquity, #architecture, #artificial intelligence, #artist in the machine, #auto-bio, #auto-fiction, #cartography, #community, #consciousness, #covers, #culture, #decentralization, #deconstructed, #delirious, #editing, #essay architecture, #futurism, #internet history, #language, #lessons from artists, #logging, #logloglog, #mastery, # music, #nature, #new york, #religion, #social media reform, #synthesis, #techno-selectivism, #time, #transitions, #virtual reality, #warped incentives, #writing online.

Let’s riff:

• What’s a favorite essay of yours you’d like to see reviewed on Dean’s List?

• What’s a key feature you’re looking for in an AI-powered craft companion?

• What’s a pattern you’re starting to notice across everything you read?

Leave a comment

Footnotes:

Welcome to Dean’s List. I’m an architect turned writer. Substack is home for all my creative projects, and a place to think through the craft of essays. This is part of my monthly update series. You can also jump to my essays and daily logs.

Should you savor in the slowness or automate existence? That’s today’s theme. It’s tempting to pick one side, coin it as a jingle, and live by it. But in the last month, I’ve seen value in both ends: unreasonable tedium & unimaginable speed. Maybe we can embrace the paradox: how can we be the tortoise and the hair, the slug and the supercomputer?

33 hours for 3 minutes of totality_

I ended up catching totality (a full solar eclipse) in an ex-hippy-commune town in northern Vermont. My dad and I spent 18 hours driving, 3 hours researching in a motel, 5 hours not being able to sleep on a stiff, small, shared bed, 3.5 hours scouting different sites, and 3.5 hours waiting in blue fold-out chairs. All that for 3 minutes. Our “effort-to-experience ratio” was 660:1. This sounds pretty unreasonable, especially if you don’t grok the numinosity1 of totality. Annie Dillard said the difference between a 99% solar eclipse (through the goofy glasses) and totality is the difference between “kissing a man… [vs.] marrying him.”

Eclipse photos—whether from NASA or an iPhone—can’t capture the thrill of the chase, the extreme anticipation, the fffwwwooooppp moment of a sunset on 200x speed, the 3-minute mystical experience where you confront and overcome death, and the second after totality where beams of light pierce through the mountains of the moon (it’s so beautiful you don’t want to look away; this is how John Quincy Adams went partially blind).

This is one of those experience where prose beats pictures.

When I got home, I wrote on my typewriter to capture the emotional power of the experience. It’s been a while since I’ve done a first-person narrative essay like this, but I’m really happy with how it came out. Hope to do more like this soon. Usually my analog essays are for paid subscribers, but I made this one free.

For some more reading on totality, check out Tim Urban’s post, or Annie Dillard’s essay, Total Eclipse, from 1982 (which I haven’t read yet for anxiety of influence).

2 albums in 2 days_

In the last 10 years I’ve released 2 albums (one where I tried too hard and another where I didn’t try at all—a spoof of the Beatles at Shea Stadium where the screaming crowd is an instrument, and a time traveller brings a synth from future that shuts down the show).

After trying Udio last week, I published albums on Thursday and Friday.

Writers might enjoy the end of the 2nd album, which includes pedagogical hits like, “The Punctuation Family,” “Mr. Dictionary,” and “The Feedback Song.”

There are still huge limitations with AI songwriting. I can’t use my own voice, I can’t play instruments to write riffs, and I have no precise control over song direction. To shape a song in Udio, you: 1) set the mood with a prompt, 2) write lyrics with instructions in parenthesis, and 3) listen through the 30-second variants, make tweaks, and extend clips. Despite the limitations, both the audio quality & the musical intelligence are radically improved from 2020’s Jukebox (the tech behind the AI Beatles music I wrote about).

We’re not at the point of “one-click wonders” yet; it took time to make these. From these 23 tracks you hear, there are maybe 200 bad stems that didn’t make the cut. And while the instrumentation is effortless, I wrote 95% of the lyrics.

Still, the process of writing an album goes down from one year to one day. If I committed to this, I could release a concept album per day.

What’s amazing to me is how the lyrics bear so much influence on what the songs become. My main flaw in songwriting has been that I ignore lyrics until the very end of the process (I use non-sense placeholder lyrics while I shape melodies and song structures). Now, it’s entirely about the words. It is the single given, the center of gravity that harmony and rhythm bend around. Many of these songs include lyrics from songs I wrote in the past, and it shocked me how some of the melodies matched one’s I already wrote, and how some melodies are way better than the ones I came up with. It’s like the words have an invisible inner-logic on how they want to be made musical, and AI helps you quickly discover that.

AI music has a ton of wrenches and philosophical problems (this app was made in collaboration with Will-I-Am, and seeing The Black Eyed Peas perform at Ultra Music Festival in Miami in 2009 was a low point in my life), but I’m mostly excited. This is a tool for poets and writers to add a new dimension to their ideas.

Reading 7 dictionaries A>Z simultaneously

Reading reference manuals in full is some people’s idea of torture, but this is now my preferred form of procrastination. At least once a day, I’ll sit down and read a few pages to mark down the words that stand out; when I get bored, I’ll shift to the next book. I’m up to “Ad—” and hope to finish by EOY.

I never appreciated the weird niches of physical dictionaries that exist: dictionaries for myths, symbols, theories, literature, rhetoric, origins, etc. I found something like “a dictionary of time” (a record of all events that ever happened) but it was too big to carry. While there’s something clean and efficient with a searchable database, an obscure physical dictionary is like a landscape with hidden gems; I leave each session with something like 50 new words. I come across concepts I’d never find in my normal reading routes.

It’s not just about reading these dictionaries, but sifting through noise, finding hits, researching them, and then redefining them in my own way. I’m slowly building a collection on my site (link below).

I also got Roget’s Thesaurus—in dictionary (A>Z) form—and was pretty disappointed. The word “belief” has a 187-word word-cloud; are we to assume these are all swappable synonyms? Each word should have a unique usage. I’ve been doing some thinking on a better architecture for the thesaurus; the scope is unfortunately ridiculous (the entire English language lol), but maybe I’ll work on that after Essay Architecture.

Essay Architecture_

Sometimes I’ll isolate essay patterns, but sometimes I’ll deconstruct a full essay. In case you missed showing vs. telling, here’s a video breakdown of David Foster Wallace’s, “How Tracey Austin Broke My Heart.”

The next post in the EA series is about a response. It’s one of the patterns in how to craft a thesis. Where the microcosm pattern is about scoping down your frame to reveal a larger truth, the response is about getting out of a vacuum. Even the most original ideas exist in context of things already said in the culture. The book They Say, I Say, is about framing your thesis as a response to an existing idea.

Here’s a WIP diagram on the different ways to do it:

Go touch paper_

Still chugging through my essay on the Apple Vision Pro, but wanted to share a picture from 10 years ago that shows my “spatial operating system” in architecture school.

06: Alchemy for writing and being

Check out my post on assay vs. essay. The word “essay” comes from Michel Montaigne, but it’s cousin-word, “assay” was used by the alchemists 100 years before. These words represent two opposite halves of a process. When you constantly shift back and forth between them, you turn ordinary insights into linguistic gold.

I’ve been getting into the alchemists; it seems like their whole philosophical worldview is about the fusion of opposites, which is a pattern I’m seeing more and more in my own life (ie: this post about efficiency vs. inefficiency).

I’ll have to do a deeper dive on the alchemists one day, but wanted to share these two quotes for now:

From Brene Brown (quoting Jung, quoting the alchemists):

“Carl Jung wrote, 'Only the paradox comes anywhere near to comprehending the fullness of life.' We are complex beings who wake up every day and fight against being labeled and diminished with stereotypes and characterizations that don't reflect our fullness. Yet when we don't risk standing on our own and speaking out, when the options laid before us force us into the very categories we resist, we perpetuate our own disconnections and loneliness. When we are willing to risk venturing into the wilderness, and even becoming our own wilderness, we feel the deepest connection to our true self and to what matters the most.”

From Hermes Trismegistus (the OG alchemist):

"If then you do not make yourself equal to God, you cannot apprehend God; for like is known by like. Leap clear of all that is corporeal, and make yourself grown to a like expanse with that greatness which is beyond all measure; rise above all time and become eternal; then you will apprehend God. Think that for you too nothing is impossible; deem that you too are immortal, and that you are able to grasp all things in your thought, to know every craft and science; find your home in the haunts of every living creature; make yourself higher than all heights and lower than all depths; bring together in yourself all opposites of quality, heat and cold, dryness and fluidity; think that you are everywhere at once, on land, at sea, in heaven; think that you are not yet begotten, that you are in the womb, that you are young, that you are old, that you have died, that you are in the world beyond the grave; grasp in your thought all of this at once, all times and places, all substances and qualities and magnitudes together; then you can apprehend God."

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Let’s riff:

• The eclipse, the hype …

• AI music…

• Words, language, essays…

• Alchemy…

• Convenience vs. inconvenience…

I expected to love this thing. I daydreamed about a writing workflow where information levitated around my typewriter. I’d fuse analog and digital. I’d be a pioneer.

I returned it after 2 weeks, not just disappointed, not just disgusted, but so paranoid about technology that I’m questioning the whole foundation of my digital life.

My Notion system was transferred to a system of legal pads and index cards. My logs now get captured in a college-ruled Composition book. I’m reading the dictionary. I hand draw maps of my neighborhood. I shop in stores. I walk, too. Most extreme, I’ve been “off the clocks” for 10 days now: my lock screen is in Cambodian, and every device is in military time, set to different time zones. Once a day, I set timers so I can catch trains and meetings. I haven’t missed one yet (I’m remarkably early for the first time ever). If I ever really need the time (I rarely do), I can either go to my stove or time.gov.

Now I get that this sounds like an extreme overreaction, and if you’re anything like Chris Wong (the first reviewer of this draft), you might be asking, “did you see a monster in there?” No. I saw peaceful lakes and magical maps and full-scale memories. I turned my fig tree into ChatGPT. Notion windows, everywhere. My heroes sung to me on massive screens while I washed dishes and vacuumed dirt. I watched the Superbowl on a 165” crystal pane, and it made my 65” Samsung Frame look like the small TV in my parent’s kitchen.

Any given feature is profoundly cool the first few times you use it (this is why the Apple Store demos are a hit), but they all conspire together for a more sinister truth. If you actually want all this magic functionality in your life, you have to wear the brick all day. You can, and when you do, you get accustomed to your consciousness being locked into clear, huge, mesmerizing screens, everywhere you go; by contrast your own apartment is seen through grayish, fuzzy, CCTV camera feeds: good enough to get around, but too fuzzy to read the words in a printed book.

It’s the epitome of a Faustian bargain:

The Vision Pro brought a lucidity to my (/our) relationship with technology: a fetish for technological awe and an unspoken religion of tyrannical convenience. We are in a cult of efficiency. Each year we’re pulled further into a frictionless sensorium; the reasons to upgrade are a no-brainer, but the amputations are invisible.

So the last few weeks have been a slow process of experimentation. I’ve been re-evaluating all the technology I’ve uncritically adopted. What might I gain back? I’m neither Luddite nor Cyborg. Instead, I scrutinize my tools. Does adding or removing this feature make me more or less embodied, creative, social, or grateful? The goal is to design a mosaic of doohickeys that work together to bring me closer to my own idiosyncratic sense of purpose. It results in a weird and seemingly bizarre combination of the old and new. I’m calling this stance: “techno-selectivism.”

If I build a sundial, I’ll make sure to record it with AI-powered smart glasses.

Here’s what I’ve published recently:

Typewriter essays_

I published 12 typewriter essays last month to a secret sub-list of Dean’s List (this is another bonus of becoming a paid subscriber). If you want them in real-time, you can opt-in through your account settings by turning on the Analog section. This batch covers reflections on technology, analog life, some dreams, memories, and film reviews, and an experiment on what it’s like to be a Batman.

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Logloglog_

1. Tim Cook’s eyes
   February 1st, 1:24 pm — Tim Cook is on the cover of Vanity Fair with the title "Moon Shoot." It’s the first time we see him in a headset. He’s not embarrassed! Unlike the quirky TIME cover of Palmer Lucky in 2015—where he’s levitating on a beach with a big wired headset—Cook is calm. In an ergonomic chair, he’s got casual shoes and a sleek watch, against a minimalist wood desk in a bright room, with a background that shows a football helmet and some unhung art—he’s a regular guy, just like us. But something is off with his eyes. It is technically marvelous that inner cameras can detect his retinas and re-project them onto the outer glass of the headset, but in this very clutch moment where the world sees TCook in VR for the first time, his eyes are dreary like hell. Is he asleep? They’re barely open, a half-squint, shrouded in blue fog, as if he’s preserved in digital submission, some eerie limbo where he can’t be fully conscious.
   
   

2. On getting stuck in holes
   February 5th, 6:41 am — On the LIRR to Grand Central, everyone is on their phones (it’s almost not even worth reporting on this because it is obviously the default and has been so for a decade). It just feels notable to observe this on route to try out the new AVP headset, which some people have described as a “religious experience,” and also a “BC/AD” moment (meaning once you try it on, there is no coming out). This is roughly the 10-year anniversary of me trying my first virtual reality headset. I went to my friend’s apartment in Astoria and tried the DK-2: a plastic, taped together rectangle, 960x1080 and only 1 million pixels in each eye (23 times less than what I’m trying today). It had the screen door effect, it was impossible to read text, and was at times extremely nauseating, but I remember looking at a digital horizon from that Oculus Villa and noticing my eyes adjust, and probably said some true cliche like: “wow, this is the future.” That was produced by a kid on Kickstarter, and today’s experience will be by one of the world’s leading technology companies.
   
   

3. I prefer Ping Pong
   February 7th, 9:11 pm — I’ve put my finger on what bothers me about the Vision Pro compared to other wearable tech I own. The Quest has clear, limited use-cases: I can jump in for a 3D architectural review, or to get my heart rate up with Beat Saber, or to play mini-golf or ping-pong with friends across the country. I’m in and out in 20-60 minutes.The Rayban Stories are an always-on-your-face technology, but they disappear. I forget they’re there, and yet when I need them, I’m actually “augmenting” something—taking video, listening to music, or on a call. But the Vision Pro is an intrusive, all-encompassing device. It doesn’t (yet) offer new use cases, it’s an OS that magnifies the core things you already do. The implication then is for you to wear this all day; and in-exchange for surreal and powerful digital experiences, your eyes are replaced with a CCTV feed—one that is surprisingly good, but is still—filled with blurriness, artifacts, and glitches. The AVP is the philosophical opposite of the iPod, the Apple Watch, and the Airpods: those disappear, while this one replaces your window to reality. It intrudes on your sight, your most fundamental tool of sensemaking. It asks you to trade in the core part of your human experience for $4,000 and $25/month insurance.
   
   

4. Aliens at the Super Bowl
   February 11th, 6:30 pm — Commercial 1: features the apocalypse and aliens (a Quiet Place 3?). Commercial 2: an unrecognizable quarterback gets sucked into a street portal and the other actors don’t seem to mind (to sell Dr. Pepper). Commercial 3: opens with a red, swirling hypnosis portal. What’s with the alien theme? The biggest event in our culture was peppered with 10-15 allusions to extraterrestrial life. A conspiracy theorist would call this predictive programming, but it likely boils down to marketers all coming to the same conclusion independently. A social media analysis probably determined that the top 2 things on people’s minds in 2024 are celebrities and UFOs. It’s just market research. Give us shape-shifting Tom Brady.
   
   

5. Philosophers, directors, poets
   February 15th, 9:00 pm — A writer is a philosopher, a director, and a poet. They’re a philosopher in their concern for truth and in mapping webs of ideas. They’re a director in the sense that they have to produce a single linear cut through all possible cuts. They’re a poet in the sense that every sentence is a work of art.
   
   

6. Electronic tribalism > personal hallucinations
   February 15th, 6:09 pm — AI and the death of Hollywood; that’s the theme of X today. From a simple prompt, you got a multi-shot 60 second trailer. Unlike last years’ grotesque demo of Will Smith eating spaghetti medieval style, this is smooth. What are the second order effects? For one, if everyone is watching their own custom-generated films, then shared culture dissolves. If the Internet brought us from mass-media to electronic tribalism, then AI brings us from electronic tribalism to personal hallucinations. Media no longer serves the role of a unifying fabric. I can’t go to a friend and rant about the movie The Lobster and immediately get into conversation about it—instead I’ll have to go, “do you have 90 minutes to check out this wacky thing I “made?” The answer will be no; they’ll have a whole playlist of wacky things they “made.”
   
   

7. The point of scoring essays
   February 18th, 9:40 pm — I’ve been scoring the classic essays I read; so far the scores range from 5.9 to 8.5 (out of 10). I’m definitely wrong on many sub-points, but the exercise is helpful. An important note: an essay score can’t access the originality or merit of an idea. Instead, it measures the completeness in the components that good essays are known to have. There are patterns in ideas, structure, and voice, that can all be synthesized together into a unity. Brilliant ideas might ignore these patterns, and find a hard time resonating with an audience. A brilliant idea in a bad essay might be in the 6s, but an okay idea with solid form could be in the 8s. Learning the core components lets you shape a sound vessel for whatever experience or theory you want to share.
   
   

8. Clocks go TikToK
   February 18th, 9:55 pm — There’s a lot to the name “TikTok;” it’s not just an alliteration, but an onomatopoeia: the app is named after the physical sound of the second hand on an analog clock. It’s an allusion to the passage of time, that in some fundamental way, TikTok is re-writing. They are delivering a carousel of media universes that can be flicked through faster than the clock ticks. Empty time is replaced by delirious saturation. We are not built to occupy 60 worlds-per-minute (relevant: addled)
   
   

9. Go for a walk and try Plexus
   February 19th, 1:02 pm — The “playlist” feature on Plexus makes the whole concept of voices click for me. It’s meant for walking outside. You start by unpacking what’s on your mind, and then you surrender to the resulting stream. It’s a flow of unoptimized 60 second rambles that have the associative nature of the movie Waking Life. The experience of the app feels like a late-night winding conversation, an intimate experience once reserved for dorm-room friends, now undertaken with strangers from around the world. It is screenless, feedless, honest, and inviting— the opposite of today’s paradigm—and could be a monumental force in finding the others. The key challenge is that it asks someone to change their clock speed. There’s no skimming or scrolling, no navigating to find that “aha.” You have to be patient and open with what’s presented to you. As Plexus scales, the level of uncanny resonance could be so high that it overrides the need for cheap hits.
   
   

10. Platonic relationships
    February 20th, 12:49 pm — platonic : (adj) A “platonic relationship” has come to mean a non-sexual one, which is revealing. Google it. It’s seen as a second-rate, friend zone situation (“you mean you’re spending all that time together and not fucking?”). “Platonic,” comes from Plato, who sought to break things down into their purest forms. Any realm is composed of invisible underlying components. In the same way “the platonic solids” refer to the elementary 3D shapes, Plato’s writing on love outlined the full range of dimensions that could exist within a relationship. Through this lens, you might think a “platonic relationship,” is one that includes all possible facets (compatibility, trust, respect, vulnerability, coevolution, insider slang, shared values, shared stakes, a common history, etc.). By re-defining platonic as “not sexual,” we’ve not only declared sex as the pinnacle of what a relationship can and should be, we’ve not only collapsed the rich nature of a human bond into “sex” or “not sex,” but we’ve lost the word to describe Plato’s method of thinking. The word “platonic” could refer to things outside of relationships, but when I tell people that my Essay Architecture project is platonic, they look at me funny. Horniness hijacked the name of our best philosopher.

    Load 312 more

Let’s riff:

• Do you keep any analog habits that are hard to justify to others?

• Thoughts and feelings on emerging technology in 2024?

• Which logs stand out? What should I bake into an essay?

I had the pleasure of spending my last half of January in Athens. Greece is obviously a summer place, but if you enjoy ruins, go in the winter. In August there are over 20,000 daily visitors on the Acropolis, but I watched the sun rise over the Parthenon with approximately 9 people. At lunch I had the Roman Agora entirely to myself.

The point of this trip was to meet my nephew, a 6-month old international traveler whose passport says, “Occupation: Baby.”

During the days I’d see family or archaeological sites (I finally went to Eleusis), but thanks to jet lag I wrote a lot between 1-5 am. Half that time was writing about my trip (see: logs from Jan 17-28), and the other half was drafting out the upcoming chapters for Essay Architecture.

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ANNOUNCEMENTS_

1. What makes a good thesis?

   1. Thanks to everyone who signed up for Essay Architecture!

   2. I’ve drafted out the first 4 chapters and can’t wait to share them with you. In February we’re unpacking the idea of a thesis. When you hear the word “thesis,” what possibly comes to mind is a 426-page typewritten dissertation that took three 3 years of library hunkering before it got ransacked by a committee of heads in suits. That’s not what I mean. A thesis is the central (but elusive) idea that unifies all the material in your essay. A good one has 3 facets:

      1. a microcosm (a small frame that illustrates a bigger pattern);

      2. a response (that puts your idea in context of existing ones); and,

      3. a catalyst (how someone might change after reading it).

   3. Paid subscribers will get a full essay for each concept (you can join for $10/month).

   4. Here’s a preview of some visuals I’m working out for the first post.

      

      ---

2. Daily Feedback Sessions in February!

   1. Feedback is the key to refinement. I’ve set up the Writer’s Studio so you can book live feedback calls whenever you need them. You’ll leave each call knowing if your sentences land, and also: the best part, the worst part, and an open question. Bring a draft, get feedback, edit, then bring it again, as many times as you want. More details here.

   2. For $300/month (the Founding Members tier), you can join a network of craft-focused writers.

      

ANALOG_

I published 7 of these one-pagers last month. They’re around 500 words each and take 45-60 minutes to write. Some of my favorite essays are now coming through the typewriter.

These are all on my paid tier, but I figured I’d share one so you get a sense of what it’s like. Everything exists in the Analog section, and you can choose your frequency: you can opt-in to get them in real-time, or, you can binge them all at once in my monthly listicle (list below).

Typewriter essays in the last 30 days:

• aliens in miami, when portal-peddlers are also growth hackers

• lucid dreaming on-demand, the century of the subconscious

• the art vandelay effect, george costanza & the creator economy

• AI george carlin, entering the fan-fiction hallucination vortex

• on tinnitus, what to do with the humming in your head

• a private universe of practice, audiences and accountability

• shapeshifting calligraphy, a handwritten essay on graph paper

Unlock the typewriter show

10 logs on Eleusis, historical encryption, the terrible future of news, VR, the demise of typewriters, the ideal vice president, religious reform, where to hide the nuclear codes, polymathic websites, and how to type 360 words per minute.

1. Writing as literal architecture | Jan 27, 12:52 pm — On the site of Eleusis, there were dozens of eroded columns that had long paragraphs (/atomic essays) of Greek writing on them. I hadn’t seen such a volume of text on anything in the Acropolis or in its museum. Reading was part of the initiation that helped frame the psychedelic experience (read: Resurrections on Demand). Makes sense that you couldn’t “pledge” unless you could read Greek. Very cool to see medium-form writing as an architectural element.
   

2. Why are the Eleusinian Mysteries encrypted from history? | Jan 25, 1:05 am — Eleusis was such a massive part of antiquity’s religion, but it was barely mentioned or studied in the Renaissance. Interest in it didn’t really emerge until the 20th century. Some thoughts on why:

   • Greece was under Ottoman control, and it was hard to access archaeological sites. After the Renaissance, it took 200 years to re-discover Eleusis, and then 400 years to excavate it (1882).

   • The site was completely demolished unlike some other ruins, making it hard to appreciate its grandiosity (the Telesterion temple at Eleusis was 13% bigger than the Parthenon).

   • It was a walled “necropolis” that was 13 miles away from Athens, meaning it was out of sight and far from where most were drawn to studying.

   • The secret nature of the cult meant that it was historically encrypted. There is little written record of the rituals, either because they were destroyed, or because much of it was passed down orally.

   • Religion was a sensitive topic in the Renaissance; humanism was already a challenge to the established Christian church. Paganism was a non-starter; the revival was more around aesthetic and intellectual fields: art, architecture, sculpture, literature, law, democracy, etc.
     

3. When bots create news clips based on what’s trending on X | Jan 16, 2:36 pm — Right now, the #1 thing going viral on X is—ironically, under fashion and beauty—pornstar Mia Khalifa. Bots read everything in the feed, pull it into a dossier, and that gets fed it into an AI prompt like, “summarize this into a 1-paragraph statement.” It outputs something bland and shallow like: "Popular Lebanese adult film star Mia Khalifa is trending today after being confronted by an Israeli woman outside an airport in a video that has since gone viral." Content is born. Along with it is an unrelated video of Mia dancing in lingerie and making stupid faces as she sings to the Arctic Monkeys. This whole thing is wrapped in a CNN-looking UI, with a “breaking news” sub-header, the time, and a ticker. It’s called GNN. The punchline is that the statement is being read by an AI-generated news anchor, a plastic supermodel who calls herself Leslie Bombshell, stopping all the scrolls, making it more likely for this video to hack the algorithm.
   

4. Apple Vision Pro | Jan 30, 9:43 am — Many of the Apple Vision Pro unboxing reviews feel off in tone and perspective. They tap into the average consumer’s cliches about VR and don’t acknowledge any of the 50+ year history behind this moment. They’re all anchored in cheekiness: a Wall Street journalist rented a cabin in Camelback to go skiing in the headset, because yes, they look like goggles. She even implied that the killer-app was cutting onions. Many other reviewers made jokes on how it would be weird to masturbate inside of the AVP because it’s always tracking your hands. Another reviewer showed 8 apps floating in a sphere around them, including one on the ceiling—an ergonomic nightmare. The Verge insisted on comparing this device to our perceptual system instead of consumer device. Since it can only display 92% of the industry-standard color space, it’s a deal-breaker. Semi-realistic avatars are created in under a minute, but they’re not absolutely perfect. FFS, the pixels are smaller than red blood cells, but it’s still a screen. These reviews have a weird anti-VR peskiness to them; they don’t think it’s feasible until it’s a weightless, perfect, tyrannical illusion. I’m happy the wire is gone.
   

5. Typewriter as endangered species | Jan 23, 1:31 am — In 2011, the last typewriter production facility—in Mumbai—closed down. After 150 years of production, they now only exist through second-hand stores, flea markets, and Etsy. I wonder how the total volume will decay through the decades. It’s crazy to imagine how all screens might undergo this same fate (TVs, laptops, monitors, and phones). Someone in 1942 would have never imagined that typewriters would become obsolete. Computing as we know it might be halfway through it’s life-cycle, and by 2100, we could be in a completely different paradigm.
   

6. AI VP | Jan 6, 9:28 am — Short story idea: a politician’s vice president is an AI bot named Washington II. It can simultaneously talk to millions of Americans at once, understand their problems, synthesize them in real-time, and guide the policy for a politician. The human figurehead is just the face, a familiar looking and trustworthy person, honest about the fact that his invention is better at “representing the people,” than him or anyone else running.
   

7. Rejectionists vs. reformists | Jan 26, 10:43 am — There are two ways to be critical about religion. One is to see its faults and write off the whole premise; a rejectionist might value non-denominational spirituality. The other sees the momentum and values of the established faiths, and seeks to reform them so that they can:

   1. encourage fundamental questions (around our origins, purpose, ethics, and death) instead of fundamental answers, and,

   2. offer rites of mysticism, transcendence, and consciousness-expansion, instead of literary and moral beliefs.

   As a reformist, I’m isolated without a camp: atheists don’t get my respect for Christianity, and Christians find me slightly heretical.
   

8. Fischer Protocol (nukes) Jan 5, 11:50 pm | The Fisher Protocol was a proposal to embed the nuclear launch codes into the heart of one of the President’s advisors. If he wanted to launch a bomb (and kill millions of people), he’d have to personally kill his own advisor, cut open his chest, and take the codes out himself. It takes the abstraction out of mass destruction. It’s not just numbers and buttons, but the embodied nausea of taking a human life. It would be far less likely to ever happen.
   

9. Website advice for polymaths | Jan 13, 11:42 pm — Internet bloggers are often advised to start with extreme legibility, so much so that they’ll have different websites to house the different sides of themselves. I think you should start the opposite way: centralize the chaos and then gradually organize.

   • Keep everything in one place; my obvious vote is Substack. A fragmented self is hard to maintain and sustain. Create a single place that has the permission to contain everything and anything. This lets it evolve with you. A branded channel is bound to die, but your personal time capsule could live as long as you do.

   • Start with as little segmentation as possible. Don’t worry about sections or tags before you have any posts. Allow random topics to co-exist. Little by little, you can add legibility and make it easier for people to navigate your maze. I try to revisit my “cartography” every 6-12 months. I look back at my old posts, find patterns, group things, and move on. Anarchy forward, order in retrograde.

   • Use sections and tags. You can organize posts across two dimensions. Sections are the “major” mode, since subscribers can opt-in and opt-out of specific streams. I group sections by medium (essays, updates, analog, craft, etc.) Tags are the “minor” mode, and can connect ideas across your sections. I might have posts across different sections that mention “Greece,” so I can make a tag for that. Every section and tag get their own URL. This means if someone says, “Do you write about Greece?” I can send them michaeldean.site/t/greece for a full curation.

   • You don’t have to blast everything. The default is to send every post to your whole email list. However, if your site is an aggregator of everything you think, then you might annoy your audience by emailing them 5-10 times per week. Consider ghost posting. You can curate the best of what you make in a weekly/monthly round-up (ie: this).
     

10. Stenography | Jan 1, 11:19 am — I’m fascinated by stenography and shorthand for the opposite reasons of cursive and typewriting: speed. Gregg Shorthand was taught in US schools in the 1920s, but my generation has never heard of it (what’s bound to happen to cursive). Shorthand is a phonetic system; each sound is a specific pen squiggle, and you connect the sounds to create a pictogram. They even have “StenoKeyboards”— instead of typing, you do something called “chording” which involves hitting multiple keys at the same time. The speed is remarkable. A professional stenographer can type 360 words per minute (with 99% accuracy)! I’m a pretty fast typer, and that’s at least 3x faster. A stenographer can even reach 250 wpm by hand. Stenographers are known to capture conversations, but they can capture ideas faster than the mouth can talk. What if I mastered shorthand? How would that effect the transcription of mind to page? Might be interesting to practice two modes at the same time: slow cursive and fast steno-chording.

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• What have you found to be the most important dimensions of a good idea?

• Thoughts on Apple’s Vision Pro?

• What most irks you about February? (Super Bowl Ads? Valentines? The 29th?)

• Favorite log?

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I’d like to put speculation to rest; this newsletter is going high-concept…

Dean’s List is now a listicle.

There’s a cosmic irony here; I set out to create timeless essays that would one day get featured in anthologies curated by Phillip Lopate, but hidden in my name is the medium known for clickbait, SEO-filler, and quizzes like “10 questions to know if your OCD is life-threatening.” I feel the call to hijack the listicle and use it to structure my creative spatters.

Plus, a monthly list is a functional move that aligns with an announcement I’m eager to share:

I’m grateful you’re here, and find it surreal and fulfilling to have many of you read and respond to my essays. I’m starting my 4th year of writing online, and it’s the year I make it my main thing. I consider myself fortunate to even have a chance to make an independent living writing, reading, editing, and teaching the architecture of essays. 

It’s weird and significant to me that my origin point is my destination. My first published essay—Studio Culture, in July of 2020—was about what writers could learn from architecture school. Half-a-million words later, it’s now the shape of my future.

I’ll be sharing more specifics on paid subscriptions in my next post, but here’s the gist.

• For $10/month (or $100 a year), you’ll get Essay Architecture, and everything in the Craft and Analog sections of my site.

• For $250/year, you’ll get a Calendly link to get (live) flash feedback from me or someone in the Dean’s List community, whenever you need it. 

• I’m also looking to work closely with ~10 writers in 2024 to shape essays at the edge of our shared ability.

The introduction to my textbook comes out soon, and I’m offering a 20% discount if you sign up before it launches.

Now let’s do the listicle-from-hell thing. I’ll reflect on the ripples of some 2023 essays, introduce you to my typewriter experiment, and share 10 logs worth reading from December 2023.

3 unexpected side effects of spending too much time on long-form essays that have nothing to do with metrics (or, the consolation prizes for someone who sucks at self-promotion)

Exactly a year ago I shifted my whole website to Substack. Before that I was posting essays into the void of Squarespace, Notion, and Ghost with basically zero response, recognition, or growth. In 2023 I grew from 216 subscribers to 878. Even though I get completely absorbed in the refinement process, spend basically zero time promoting my work after I’ve essentially slaved over it, and then immediately move to a different rabbit hole, the Substack network must have given me the minimum viable juice to gain some traction.

I’d like to learn to love promoting my work. But what’s actually more amazing to me is the tangible serendipity that came into my life without having a basic handle on distribution. By existing online and trying to do the best work I possibly can, things seem to happen.

So here’s a collection of essays from 2023. Instead of focusing on the subject matter or the stats, I want to share the unexpected side effects that came from chasing great work instead of metrics. I haven’t really talked about this dimension of “opportunity,” but the point is to maybe inspire you to pursue a slower cadence, get an extra re-write in, or try something that pushes you out of your comfort zone.

• I found the others— Just as soon as I figured out Twitter growth, I completely disappeared from the Internet and spent 50 hours in isolation working on Burn Down the Stage, shifting through 8 versions, spending a lot of time researching. I had serious tunnel vision. At a meetup someone asked me, “what do you write about?” and I just said, “American Idol.” When I first published it was anti-climactic, but over the weeks I started to hear from people in the social media counter-culture. I was emailed by writers I admire, got invited to meet with a NYC founder who is building a new feed-architecture, and got published in a physical zine. I’d been ranting about this idea for ~5 years to friends and family, but writing about it put me in contact with the others who were doing something about it.

• I was mentioned on Ribbonfarm— Without realizing, I published Lucy in the Sky of Large Language Models on the same day the Beatles released their AI-produced song: Now and Then. It was bizarre timing, especially since my stretch goal for Write of Passage was to meet Paul McCartney. I imagine I could’ve gone viral if I promoted myself, and naturally I froze. When I saw another AI Beatles essay get featured on Substack Reads, it confirmed that I fumbled. But weeks later, I was reading Oozy Intelligence in Slow Time, an article on Ribbonfarm by Venkatesh Rao—who I think is one of the best sense-makers of our time—and unexpectedly saw my essay linked at the bottom. I forgot I tagged him. It’s a reminder for me to not only write from experience, but to link my ideas into the conceptual currents around me. My essay wasn’t seen by a 100,000 people, but it was seen by a specific person I have extreme respect for.

• I connected with my hero from Internet history— My whole logging practice started in 2021 after I came across links.net, a website started by Justin Hall in 1994. Walter Isaacson wrote about him, and Justin even made his own 40-minute documentary, Overshare, but I felt compelled to write my version of his story from the angle that inspired me.

• In September I spent an incalculable amount of time navigating his HTML maze, reading every single DAZE entry from his 1996 logs (probably over 100,000 words). It was more research than I’ve ever done for an essay. I ended up with The First Online Writer, a 7,900 word curation piece with 128 links.

• On a call with my writing group, we were reflecting on how we’d each share our monthly essay with the world. Instead of trying to promote this, I said, “the ultimate win would be if I sent this to Justin and he started writing again.” He hasn’t been posting much since 2005, but I found his email on his website. I wrote him a fairly long message in response to something he posted in 1996–28 years ago!–and linked to my essay.

• Two weeks later, he wrote back and was extremely kind. I checked his website on New Years Eve, and he said he’s itching to write in 2024. I have no idea if I had any influence on this, but either way it’s a reminder to me that an essay doesn’t have to be written for the world, it could be done just to thank one person.

11 things I may one day regret sharing, but by putting them behind a paywall I’m semi-confident I won’t get in too much trouble

Analog habits are refreshing. I’ve been writing one-page essays each morning on my typewriter from 1956. Unlike my long-form pieces that are slow and structural, these are fast and unhinged. It’s my shadow practice. It sharpens my prose and it’s a space to unpack anxieties, dreams, memories, theories, and elf languages without much of a filter. For that reason, I want as few people to see these as possible. By putting these on a paid tier, it means I know I’m speaking to people who support me and are curious to learn how writers practice outside of publishing.

• Dec 31st — one year I’ll piss my diaper at the center of the world as they reset the calendar

• Dec 30th — my made-up word for 2024

• Dec 29th — an ode to CansaFis Foote

• Dec 28th — 98% of my readers…

• Dec 27th — tring doobayonkie foofa foofa

• Dec 26th — one-page annual review

• Dec 24th — how to rewrite Infinite Jest lol

• Dec 22nd — the geometry of writer’s block

• Dec 21st — brief excursions in the dark arts

• Dec 19th — when your destiny is a listicle

• Dec 18th — heart surgery & xmas tree farmers

All my typewriting experiments can be found in the new Analog section. I’ll continue to curate these in Dean’s List, but if you want them in real-time you can opt-in here: manage your subscription.

10 logs on trash content, prompting the subconscious, editing, leap years, leap seconds, Christmas trees, career legibility at holiday parties, patience, marketing, Substack economics, and calligraphy-based New Year’s Eve celebrations.

1. Scenes from X | Dec 13th, 6:04 pm: 1)  A dead body sliding down Mount Everest, 2) the Microsoft Excel Championship tournament in Las Vegas (won by Andrew the Annihilator 3 years in a row). 3) A Congressman has cloned himself into a voice-powered AI so he can personally call each voter and have a 1:1 chat with them.
   

2. Prompting and psychedelics | Dec 18th, 7:34 am: Terence McKenna implied that he can "prompt his subconscious" during heroic-dose psilocybin trips. "Show me Art Deco," and then thousands of objects with that vernacular appear. He can cycle through aesthetic epochs. Then he says, "surprise me," to find objects that are otherworldly. There's a feeling of "my god, if I could just take a hold of this," but it's all lodged within the trip. Then he says, '"show me what you really are," and then the room darkens and everything turns ominous and he says, "alright, back to the dancing squirrels and carpet patterns." It just points to the almost identical nature between the deep reservoirs of machine intelligence and the unconscious, matched by the tiny human's ability to use small phrases to "refocus the camera," on particular regions. The implication is that everything we've ever seen gets stored and logged away into some incomprehensible system, only retrievable again through when the visual centers of the imagination are fired up: dreams, drugs, and maybe death.
   

3. The simplest way to not hate re-drafting | Dec 21, 5:55 pm: The secret hope that "this draft is it" will get you to cling. Don’t confuse a discovery medium for a final artifact. Know when a draft is a draft.
   

4. Leap years and leap seconds | Dec 22, 11:21 am: I have gone down a rabbit hole researching leap years. Did you know there are leap seconds too? The whole reason we have these units of time is to coordinate our abstract calendars with absolute solar time. Despite our insane system, we're still 26 seconds off per year, meaning this subtle solar drift over 600,000 years will result in a "solstice reversal."
   

5. Rockefeller center tree | Dec 22, 5:29 pm: The grower of the Rockefeller Center Tree doesn't get paid. Despite losing a Norway Spruce with a market value of over $1,000, the monetary value is less than the honor of being scouted and selected. It's not like this carries any kind of prestige or credential for future selections, it's more like the rare cultural honor of being the main benefactor of Christmas; you get to sacrifice a living thing on your property for the whole morale of the country.
   

6. When your relatives have no idea what online writing is | Dec 28, 8:22 pm: In those holiday exchanges with semi-distant relatives, where you're crammed in the corner of a loud kitchen–probably blocking your aunt–and you know you only have 10 back-and-forths max to fill each other in on the last year's worth of 526,000+ hours of complex human experience, there's a tragic and comic act of compression that takes place. "How's that architecture virtual reality thing, Chris?" First off, that's the name of my very-similar-looking brother, and second, I realize I've done a very bad job updating my blood-kin on my molts. "Oh actually I write essays on the Internet now." I get that familiar what-the-fuck-are-you-talking-about smile I also get from dentists, gym trainers, Uber drivers, and other acquaintance who rightfully ask, "how's work?" I've learned to accept the illegibility that comes with freedom.
   

7. The slow lane of craft | Dec 29, 2:26 pm: Internet time is measured in hours and days, and so the solutions for transformation (more creative, more productive, more fit), are presented in terms of weeks. Truth is, personal evolution takes years and decades. It's a time scale that extremely online people can't process. The web itself has only been around 30 years, still a decade shorter than Rick Ruben's whole career. Young and restless creators should shift gears, see the long game, and exist in an entirely different lane without disappearing completely. If I had a vulturic mind, I'd say it's an "arbitrage opportunity," but the whole point is that the lane of mastery is about intense intrinsic focus, and strategy gets replaced with unpredictable opportunities that emerge because of the strange lens you've cultivated.
   

8. I’ve been thinking a lot about “marketing for artists” | Dec 31, 5:01 pm: I'm skeptical that the customer first mindset of high-growth venture-backed startups entirely translates to creators. The fragile psyche of an artist is very different than that of a Delaware C-Corp. As an artist, it makes more sense to get into the infinite game of craft, follow your own intuition, be online, and see how to make your process valuable to your audience. At a certain velocity, this artist becomes an unmistakable force, and they can get by on the patronage model. Artists make things because there's a mysterious pipeline of visions filling their head and they go insane if they don't get it out. Without making things, I'd be restless and aimless.
   

9. I spend $59/month on Substack | Dec 31, 5:48 pm: 2023 was a big year for Substack, and I've noticed more writers going paid. I'm currently paying $59/month for 9 writers; if a good heuristic is to invest 2% of your expenses to artists you enjoy, then I'm under-paying. Before October, I paid $0/month for 0 writers. This is the norm. There's a certain flip where you go from, "I don't know why I'd pay for anything since there's infinite content," to, "a healthy information diet is crucial, and if I don't pay for this, it risks disappearing."
   

10. Handwriting and calligraphy on New Year Eve | Dec 31, 11:30 pm: My New Year's Eve plans got canceled (COVID/flu), and so my wife and I found ourselves watching calligraphy and handwriting videos (YouTube algo). I've put basically no thought into this in the last 25 years. My mode of handwriting has always been fast. Get the thought down. But my experience with a typewriter got me to see the value of slower transmission; what if I wrote slow too? I ended up writing out 10-11 pages by hand. My attention would shift between shaping letters, watching the grid, minding spacing, seeing the overall page, and the thought itself. Sometimes elements would blend together in synthesis. I could definitely see this leading to some mental rewiring.

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Let’s riff:

• What are you thinking re: cadences in the new year? (weekly/monthly, essay/log, blast/ghost)

• Any stories of serendipity from publishing last year?

• Share your worst listicles (looking for inspiration).

• If you’re a champion of progress and would like to get involved in an “ABOLISH LEAP YEAR BY 2035” movement, reach out at michael@michaeldean.site.

Leave a comment

• The frustrations of a 17-unit apartment tour.

• How I failed in building “Zillow in VR.”

• Using the history of the Internet to estimate its future.

Essay flashback:

• VR will change how you hunt for apartments and houses. That’s today’s theme (with a heady theory at the end). If you want to read more about spatial technology, check out my two most recent essays on VR/AR. In Teleportation, $97/month, coming soon, I write about Apple’s Vision Pro, and how it’s the first device good enough to enable remote “co-presence.” In Dharma-Vision I unpack my 2023 experiment to wear glasses every day and record my memories.

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The nuisance of real estate tours_

Envisioning your new future on Zillow is fun, maybe even therapeutic; but touring is still an absolute nuisance. I hope future generations never have to slide into the backseat of some stranger’s car to get corralled around the city to view ripoff after ripoff.

September 10th, 2023, 10:07 am (EST)
Yesterday I coordinated an apartment hunt for my mother-in-lawn where 5 appointments were spaced out by 45 minutes. I was the driver this time. One was a maze-like 2-family with a built-in landlord, another was in a decrepit “tudor village” with a bedroom that could not fit a bed, the next two were across-the-street-replicas with unreasonably steep entry stairs, and the winner was a 3rd story unit in an elevator building with an epic “bridge view” (never thought that would be an amenity); perfect in every respect, except for the one application ahead of us submitted by the broker’s brother with a sub-500 credit score.

After 4 weeks and 17 apartments, we did it. My wife and I found a 4th floor one-BR for her mother. It was exhausting. Even though Zillow empowers the buyer in many ways, you can never trust the photoshopped pictures you see online. You have to see it in person.

Around 2017, I was the co-founder of a startup trying to fix this.

I remember carrying a glowing-red gaming computer into Zillow’s NYC headquarters. It had a handle and kind of looked like a bomb. What is that? “We’re putting Manhattan in a briefcase (give us your money).” After some bold claims, we piped our digital hallucinations into the eyes of executives.

They were impressed. Our VR-UX was definitely ahead of the curve (albeit, completely unscalable).

“Keep us posted.”

How I failed at building “Zillow in VR” (the short version)_

Our “marketplace” only ever grew to 12 units and we were out of business by 2018. Even though we failed in a commercial sense, it was quite trippy to build and experience something so futuristic. Step-by-step, you could walk around a photo-realistic 3D model of an unbuilt property. An AI-sounding voice actress explained to you all the amenities, and as soon as you found the deal-breaker, you could open a glass panel and teleport into another property. No car ride necessary.

September 15th, 2023, 12:11 am (EST)
Started a VR company in 2015, around 22 years too early.

I still believe that VR is destined to transform architecture, real estate, and basically any industry whose primary feature is it’s “spatiality” (3D-ness), but I was way off on the timing. Smart friends warned me, “isn’t it too early to build a business around this?”

Maybe I ignored their warnings because I was young, putting thousands of people into their first VR experience, and seeing them flip from skepticism to flabbergast. At least one person cried.

But when you’re working with emerging technology, timing matters.

We thought real estate companies could be the “access nodes” of our marketplace. We setup VR stations in sales centers. Traditionally, you can view ~1 building per hour in a standard drive-around. We enabled them to show 12 per hour. Despite the upgrade, they had a critical beef with our product.

“Can’t you stretch the walls in the bedroom to make it look bigger?”

Absolutely not. VR reveals 7’ Manhattan-bedrooms to be exactly as they are, completely unreasonable for a multi-million dollar penthouse. Brokers don’t benefit from a massive catalog with true spatial impressions, buyers do.

“Zillow in VR” isn’t possible until a billion people have their own headset (we’re currently over 20 million, or 2% of the way there).

Doesn’t Apple’s Vision Pro change this? Isn’t this their iPhone moment? Not quite. Think of cell phones in 1992; revolutionary for its 2G, SMS, address book, and pocket-size, but still short of it’s final form.

In 2037, everyone will have a VR headset.

Using the history of the Internet to estimate its future_

As you might know, I’ve been recently enamored with cyclical histories and the Internet’s past. It got me wondering if there were any repeating patterns in the history of computing.

Maybe you think that we’re on an exponential bend, and there are no loops. Since Moore’s Law in 1965, it appears like we’ve been on a relentless march into new territory.

But if you look carefully, it seems like the last 60 years can be broken up into two 30 year loops, each with four seasons that last 7-8 years:

• I, VISION: A cycle starts when a new technology inspires a new generation of original thinkers. [The rise of computing (1962), the rise of the web browser (1992), the rise of generative AI (2022)].

• II, CONTROL: Following this, a few institutions seize tremendous power that they’ll continue to hold through future seasons [The founding of ARPANET (1969) & the rise of Web 2 companies (1999)].

• III, ACCESS: As hardware matures, new segments of the population can get online in new ways. [Personal computing revolution (1977) & the smartphone era (2007)].

• IV, DIVISION: Once software & hardware reach maturity, we face their ultimate ramifications. We feud over it until a radical innovation resets the cycle and changes the axis of power. [Debates on online rights (1984) & digital dystopia (2014)].

Here’s a visual I made showing ~10 key milestones per phase:

We only have two full loops, but the arrival of generative AI gives us a third data point (three makes a pattern). The current moment (triggered by Chat GPT) has a spirit of divergent exploration, similar to 1962 and 1992; we’re seeing new, ambitious, and profoundly weird visions of the future.

If Moore’s law can estimate the power of the future, maybe a cyclical theory can estimate the spirit of the eras ahead. This isn’t about precisely predicting the details of the next 30 years. It’s about accurately forecasting the upcoming seasons that everything will unfold within.

Now I’ll undergo the foolish act:

September 15, 2023, 11:38 am (ET)

2022 | Vision | Generative AI is sparking “everything is about to change” sentiments. Will it change the nature of creativity? Will it take our jobs? What happens when content is infinite? It’s terrifying to some, while seizing the imagination of others. Right now we’re in the early “look what it can do!” part of the phase: writing, art, music. But soon, we’ll see it applied in increasingly specific and almost absurd ways, such as “1 million new Beatles songs by 2030.” Take any prior paradigm, and remove the constraints of cost, time, and imagination. In such a shockingly open landscape, it’s one where visions will dominate.

2029 | Control | After this divergent phase, the pendulum swings back to centralization. Institutions will learn the limits and begin to take control. Every emerging category (crypto, AR/VR, AI) could fall into a winner-take-all situation. It’s worth noting the potential curveball here. In 1979 it was the government who took control. In 2009, it was Silicon Valley startups that took control. Some fear AGI itself might experience a “takeoff event,” surpassing human intelligence, becoming sentient, and quickly amassing enough power to compete with companies and governments.

2037 | Access | The Metaverse will finally be possible when spatial hardware reaches maturity. Imagine a sleek pair of glasses paired with upgrades in human computer interfaces and AI. It will kill the need for monitors and phones. This is the logical conclusion of the “remote work” era, and also the last breakthrough in communication tech. We break out of symbolic representations on screens, and extend our perception and (holographic) bodies to anywhere on the planet. The feeling of “teleportation” will be common. Society will adjust to a world where the constraint of location no longer matters, fundamentally changing where and how people live and work.

2045 | Division | A “Singularity” type of situation could radically divide the population on big ethical issues around consciousness, technology, and death. Technology will take on the paradox of being both existential (questioning humanity) and magical (taking on the aesthetic of dreams, psychedelics, and religions). Imagine a cultural awakening similar to the 1960s, but through the vernacular of machines. Science fiction authors like Bruce Sterling (1985) and Greg Egan (1994) painted futures where people were divided into two camps, the “naturalists” and the “cyborgs” (essentially). They disagreed over how far humans should use technology to augment their minds and body. This season might be when debates on transhumanism become real. Should we alter, augment, upload, prolong, extend, or replicate our consciousness?

These seasons happen to fall in line with some notable predictions:

• Elon, Open AI, and others anticipate AGI by the end of this decade.

• Meta/Apple anticipate spatial tech will mature by mid next decade.

• Ray Kurzweil has long said that 2045 will be a “technological singularity.”

The 4 seasons all make sense to me at a zoomed out level; but when you zoom into the details of every day life (like a “real estate tour of the future”), the details seem outlandish.

By the end of this cycle, when I’m old and in my sixties, I won’t need to bug anyone to drive me around for 3 weeks, and I won’t even need a real estate agent. I’ll have an agent — a super-intelligence named Justin II.1 He can scan all of North America’s inventory in 5 seconds, layout all my possessions in each unit, and then run parallel simulations to see how a synthetic version of my consciousness enjoys his quality of life. My VR tour is simply a formality, because Justin II is never wrong.

Another 30 year loop might summon a future that isn’t just stranger than we suppose, but stranger than we can suppose.

Let’s riff:

• Are you annoyed with real estate marketplaces as much as I am?

• Are you convinced VR/AR technology can replace screens?

• Thoughts on my cyclical theory? Any add-ons or pushbacks?

Leave a comment

Check out my About page for context, and my Index for all published work.

But where did my logging inspiration come from?

Justin Hall, the first online writer_

I started logging in 2021 after finding links.net, a personal website built by Justin Hall in 1994. He’s hailed as “the founding father of blogging.”

Yes, being the first online writer is a neat moniker to claim.

But he wasn’t just the first; he had a vision for what a personal website could be that’s still beyond anything I’ve seen today.

In ‘94, the web was small enough that you could browse everything new over the weekend. So Justin set out to make his personal website site the ultimate curation project, to show the world what was possible on this weird new thing called “the Internet.”

At its peak, links.net had 27,000 daily viewers, which at the time was (to my best guess) 1% of all web traffic (for context, Mr. Beast captures 1% of today’s traffic).

But Justin didn’t just curate the Internet, he shared his whole self online. He influenced a group of writers that came to be known as “escribitionists.” The word is a cross between “scribe” and “exhibitionist” (Justin has no issues with nudity).

His website contains an autobiography, family history, write-ups about his friends, poetry, essays… just about anything he could imagine, and it’s all linked together in an insane, choose-your-own-adventure HTML maze. There are 5,000 pages in there, and I’d guess near 2 million words.

This was the original rabbit hole.

Starting in January of 1996, he updated the front-page of his website with a journal entry of what he did the day before. These were his “logs.”

September 8th, 7:32 pm (EST)
It’s written in chaotic free-verse, holds nothing back, and finds a balance between “scholarly schizophrenia,” intimate personal details, and an evangelism around the self-publishing revolution. It’s known as, “On the Road of the Internet Age.” He did a road trip across the country on Greyhound busses, where he’d crash with his readers in exchange for building them a website. There’s even a William S. Burroughs appearance (a character in Kerouac’s “On the Road” from 1957).

As I binged his daze pages, I got a high-resolution approximation of the life and mind of this 22-year old stranger. It’s not a brand, a front, or a caricature. It’s a full human sublimated into hypertext.

I’m fascinated with the idea that writing can capture and share the potent moments of life that would typically fade to memory. I already regret not writing daily when I started a virtual reality company in 2014.

So in December 2021, I decided, what if I published all my thoughts on my website?

6 lessons from 21 months of logging_

Since the end of 2021, I’ve uploaded ~3 logs a day, with the average one being 50-100 words. These are small thoughts, usually epiphanies jotted into my phone in a rush, touched up and published the next morning onto a pinned Substack page.

I’ve started a lot of weird experiments, but this one stuck.

I’ll even admit that I consider my logging practice to be more important than my practice of publishing essays.

Here’s why:

1. Practice your prose — Logging lets you practice shaping ideas into sentences, without having to worry about the puzzle of essay writing. Structuring and refining thousands of words is a different skill. With logging, all you have to do is write one great paragraph. The reduced scope is liberating. It’s writing without headache. I publish 3x more words through logs than essays.

2. You see the world differently — Logging forces me to snap out of auto-pilot and pay attention. Once you build a habit of recording your observations, it gets you to look at things more closely and from different perspectives. Any ordinary day is filled with revelations, but only if you care to notice. After I capture something, it clears out my thought loop, and gives me a fresh slate to see new things. It’s a feedback loop: the more you log, the more you notice.

3. It's a lo-fi second brain — My old note-taking systems were impersonal and mechanical. I’d hoard quotes from books or articles, and then manually organize them into some private structure that was impossible to maintain. Logging inverts the typical note-taking habits in three big ways.

   1. Original — These are your original reflections. Through logging, you build a mosaic-portrait of your life. It doubles as an archive of your memories and a bank of personal sources to draw from.

   2. Loose — No organization required. I have over 200,000 words jammed into 21 monthly text files. Categorizing, linking, and grouping is forbidden. It’s just reverse chronological. All my past thoughts are searchable, and I’m building Margin Muse so that relevant logs pop into my margins as I write.

   3. In public — Sharing my logs in public forces me to write in coherent sentences. Private note-taking systems tend to devolve into chicken scratch.

4. Freedom to go off-brand — Logging is anti-strategic. I don't have the self-consciousness of a tweet or the perfectionism of an essay. I assume most people don’t binge-read my logs, so I have no pressure to perform or narrow my scope like an entrepreneur would. It’s pure capture and expression.

5. Momentum — So many of my essays and tweets start out as logs. I often scan the past few days to sense the themes that are emerging. These are the ideas ready to be written. If ever I get stuck on an essay, it’s often because it felt urgent, but had no presence in my latest logs. Instead of starting from a blank page, you can copy in some recent logs and thread them together (this is my exact strategy for loglogog). It comes out easily.

6. It works even when you're busy — I was slammed in April and May and had no bandwidth to write essays. I still logged. I wrote 13,000 words. Logging is resilient. You don't need to make time for it. It's ambient. It's simply about making the habit to write down the thoughts you’re already having.

September 4th, 2023_

What does a day of logging look like?

Check out the list below. It shows the time that I logged, and the nature of the thing logged (if you’re on desktop, you can hover over the numbers for footnotes, otherwise you’ll find them at the bottom).

This example is from Labor Day, where I logged about every half hour. Check out the range of things captured: dreams, quotes, theories, small moments, prices of food, stupid thoughts.

Logging is about recognizing that something novel has just happened. It’s an “aha.” It’s pairing the act of surprise, insight, humor, or struggle with the habit of grabbing your phone.

• 8:42 am — Analyzing dreams from the night before1

• 9:07 am — A Hunter S. Thompson quote on the 1960s2

• 10:11 am — A Lichtenstein quote on language3

• 10:34 am — Speculating on factors that might break the Strauss-Howe cycle4

• 11:15 am — On how fame punishes those who express themselves 5

• 11:52 am — Abstract idea: history is a womb6

• 1:14 pm — Why artists shouldn’t obsess over their work7

• 1:30 pm — An analysis on the 4 era of music since 19408

• 1:49 pm — Getting high in a parking garage outside a mall9

• 2:02 pm — Idea to go viral on Reddit with a “reverse munchies” post10

• 2:04 pm — $25.17 for a quinoa salad11

• 2:13 pm — Paranoid thoughts in a public restroom12

• 2:16 pm — Making fun of aggressive police dog signs13

• 3:03 pm — Idea for a band as my wife tries on jeans14

• 3:50 pm — On solving the problem of finding clothes that fit15

• 3:51 pm — Declaring the death of malls16

Let’s riff:

• Dive into the links.net rabbit hole — what are your impressions?

• What stops you from capturing your thoughts through the day?

• If you logged, would you post them on your website?

• Would you join a “Log 100 Logs” challenge? Should I start that?

Leave a comment

Footnotes:

• I’m building an AI-powered text editor.

• The insane power of picking One Thing.

• My dad logged the first 5 years of my life.

But first, some links On Writing I published recently.

• 🔗 Perfect Practice Makes Perfect
  Writing lessons from Fat Joe, my baseball coach.

• 🔗 DEVO & Deconstructing Covers
  Permission to make weird remixes.

• 🔗 Catch the Fish or Chase the Whale?
  Advice for tackling big projects.

And also, a quick Essay Flashback:

• Burn Down the Stage — This essay looks at the influence of American Idol on social media. No matter how different each platform might seem, each is centered around a stage, with the right to be famous, and the duty to vote. It leads to a Lurker < > Idol dynamic, with a ratio of 99:1. Our goal should be to eliminate stage fright and increase posting rates. We need a “middle context,” something between the stage and DM. Imagine being able to share honest and unrestricted thoughts, but each one is somehow delivered to only the “right” people. We could use our algorithms to connect instead of addict. We need better online social circles, not a bigger spectacle. Check it out.

I’m building an AI-powered text editor.

How is a 21st century writer different from writers of the past? Probably, technology. Since GPT-4 came out in March, there’s been a shared sense that the rules of the game are about to radically change. I’m less excited about a babbling chatbot juicing out free essays, and way more excited about AI teaching me to code my own writing tools.

I’ve wanted to “learn to code” for over a decade. I know the basics (variables, functions, loops, events) through a visual syntax in Unreal Engine, but I’ve never been able to whip together an idea into a useful app. I’d always get stuck half way through a 40 hour Udemy course to learn the abstract foundations. Now, you speak detailed English into a chatbot and it spits out a broken app in 45 seconds. Through fixing feature by feature, I’ve been learning Python and Typescript.

With patience, ChatGPT, and the advice of a close friend who builds software professionally, I’m able to close the gap between an idea in my imagination and functioning code. After 3 months of fiddling, I finally have something worth sharing.

Remember Margin Matchmaker? I built it.

I strung together a crude text editor that has an AI-powered “second brain” living in the margin. It’s different from Evernote (or whatever app you use or don’t use) in two big ways: it’s semantic1 and automatic.2 Meaning, as you write an essay, it automatically pulls notes based on each sentence you write.

Writers can benefit from AI without having it write their sentences for them.

Here’s a demo of what I now call “Margin Muse” (open in full screen on desktop):

This changes how I think about my note-taking system. It’s not about organizing anymore, but capturing.

There’s no longer a need to tag, link, and groom notes. Now it’s about stockpiling sources that might be relevant to your writing. You don’t want to scrape the whole Internet, but you’ll want your own curated “hyper library,” a personal but unorganized “epiphany swamp” of things you care about.

This prototype only has 1.5 months of logs, or around 10,000 words in it. My next step is to get all my logs and essays in there, which would bring it to 300,000 words. At this scale, I’ll need to improve the UI and add a note-sorting algorithm. And once those foundations are in place, it’s a “scrape race.” 3

Maybe I’ll make this available as an app in the future, but for now my goals are: 1) getting good at coding, and 2) augmenting my writing. I don’t want to start a software company and write on the side as a hobby. I want to be a professional writer and editor that uses software to accelerate my own practice.

AI is changing the paradigm in how software gets made. GPT-4 is like a 3D printer of software. When users are empowered to make their own tools, they can design their own 1 of 1 applications.

Here’s a log from July on this:

July 19th, 2023 6:56 pm (ET) —

Consumer software manifests itself through economic constraints. I remember when Evernote cut back features to make it “simple” and accessible. The bottom line for growing software companies is that they need to onboard hoards of new users to stay alive. This means the feature set is optimized for people in their first 60 seconds in the app. This might be terrible for the power user who is 30 hours into the app.

Compare this to 3DS Max, a computer graphics app by Autodesk, with little competition or alternatives. The learning curve is huge, and the average user is 6 years deep. Beginners are tremendously overwhelmed, but the power users are super-human. The complex interfaces are extensions of their nervous systems.

If AI & no-code reach new levels of accessibility, this might enable an average person without coding experience to design their own “power tools,” features and interfaces, custom tailored to their own minds and needs, that gradually evolve over the course of their whole life.

The insane power of picking one thing.

For the last 6 weeks I was stuck on finishing this MVP of Margin Muse. I wasn’t prioritizing it, and so I squeezed it in between other tasks, giving up when I got blocked after an hour. But my wife went to the Poconos for a Bachelorette party last Saturday and I finished the whole thing in 6 hours by 2pm.

This happened because on Saturday I had only one goal: Margin Muse.

I’ve been intrigued by “the one thing” philosophy for 2 years, but I only ever considered it at the most macro scale. Some companies (Basecamp?) will only let each employee cover one project per quarter so they don’t get distracted, and so accountability is clear. In 2021, I shed some stale dreams around architecture, songwriting, and virtual reality so I could focus on one career as a writer.

But I never considered how the philosophy applies to a day’s work.

August 19th, 2023 2:25 pm (ET) —

When I have clarity on what to focus on, everything seems to magically happen. A problem will haunt me for weeks because I never commit to it, but if I just say "this is my sole focus for today," weeks worth of stress dissolves. Less micro-management and more bold decisions. Otherwise you get stuck in the valley of despair, with 5-10 things lingering, and you feel stuck and unaccomplished. Your attention is a beam. Use it. The wins compound and you feel unstoppable.

Now I start each day with one non-negotiable thing I have to finish. I have permission to ignore almost everything else until it’s done. There’s no system needed. Just a bold decision.

In the afternoons I have the opposite strategy. I have a specific 27-point checklist, that I (try to) run every day, and I even use a stopwatch to measure how long each item takes. The whole list gets done in under 60 minutes. By limiting this extremely-optimized hyper-diligent “checklist consciousness” to one hour every day, I can get away with tangents and rabbit holes with the rest of my time. The checklist is a way to “get centered,” so the next morning I can plunge into the next one thing without worrying about all the loose ends.

My dad logged the first 5 years of my life.

My brother just had a baby, and he’s experiencing a bunch of “firsts,” like the first laugh (triggered by snoring). This got my dad to remember he logged the first few years of our lives. He sent over a text file through WhatsApp. These aren’t basic milestones. I have 8,500 words of one-line logs that cover my first 5 years. They’re perfectly specific, triggering memories and connecting dots from my past.

Imagine 883 lines like this: 4

• 90,10,13, Michael Growls when he Plays with String & Gets Frustrated

• 91,07,06, Solved Compuserve Problem by Reseting Computer

• 91,08,28, Tried to Brush the Teeth of a Neighborhood Cat

• 91,11,09, Likes to get dizzy & fall down

• 92,03,15, Knows how to Eject Tape from VCR

• 92,05,08, Michael Scared of Thunder, Says I'm Sorry When He Hears It

• 93,07,31, Knows over 60 of the 84 dinosaurs in his book

• 93,08,01, Steered Golf Cart in Circles while Stephen Pushed Gas Pedal

• 93,11,22, All Concerned that Priest told him Jesus is in his Heart

• 94,09,20, Asks Daddy; when he gets old will he die?

I fed the complete Baby Logs into AI and started asking it questions (I used Claude 2 for its larger context window). I asked it to come to conclusions about my personality, my parents, and eventually I asked it to predict the career that this child from the logs would grow into.

Results:

1. Computer programmer/developer - The early interest and aptitude with technology stands out, and his problem solving and logical thinking align well with programming.

2. Teacher - His verbal skills, empathy, imagination, and ability to relate to children make a strong case for a teaching career. He seems to thrive working with younger kids.

Check out my About page for context, and my Index for all published work.

Let’s riff:

• Have you tried coding with AI? What would you build first?

• What are your pain points in the writing process?

• What annoys you about text editors?

• What prevents you from committing to a single thing at a time?

• What’s your most treasured artifact from childhood?

Leave a comment

Footnotes:

The peak of the trip was an 8-mile hike to Kaaterskill Falls, an upstate New York gem that became the object of affection for “The Hudson River School” (of landscape painting) 198 years ago. From a 10 foot cantilevered wooden plank I saw the canopies bend and swirl in exaggerated motions. I wasn’t on drugs though; the waterfall itself generates illusions if you look at it right.

August 12th, 2023 11:33 AM (ET)
Whenever at a waterfall, I’ll stare at it for 1-2 minutes. Instead of seeing it as a whole object, I try to see it as hundreds of individual currents of water. It takes focus. Then I look away and the woods look like they’re breathing. There’s definitely a technique to it. Sometimes it only lasts a second. Sometimes a minute. Sometimes it turns my gaze telekinetic where anything I look at propels 60 feet up into the air. It’s a visual puzzle. A perception hack. I feel like I’m at a James Turrell exhibit.

This is called the “motion aftereffect.” It’s nature’s version of those YouTube videos where you stare into a spiral for 60 seconds and then look away and everything looks trippy bro. It’s a mushroom simulator, but only for the shallow visual distortions. It’s a rational and explainable optical illusion; but it can’t recreate the “self-transforming” objects from the subconscious. For that, you need to actually get stoned.

Around a campfire the night before, we passed around “Gazzurple” and “Poddy Mouth,” strains of weed legally grown and sold in New York. I have a long and tricky history with weed. It’s rarely a chill-and-relax situation. I’m blessed with weak tolerance, and so a few hits can spiral me in good or bad directions. Marijuana has given me both life-changing introspections and delusional thoughts, creative breakthroughs and physical discomfort, transcendent visions and multi-day panic attacks. Usually the good outweighs the bad, but I’ve been in a weed funk since the pandemic (less insight, more paranoia). I haven’t smoked in 6 months, but I was eager to give it another chance.

August 11th, 2023 9:23 PM (ET)
2-3 hits off the Pax. Was doing a simple, soft beatbox with my mouth (something I often do without realizing) but then the “rendering engine” kicked in. I could hear my lips as a full drum set. Other sounds came in, and it started warping, from a Ty Segal grunge song, into an acoustic Grizzly Bear picking pattern in open-tuning, onto the next thing, and the next thing. And as it changed, I could see it: colors, forms, and motion, fast and erratic, like some kind of synesthesia. I wasn’t actively daydreaming songs, it was just this wild beautiful self-transforming thing I could hear and watch, warping time signatures, and shifting through inconceivable timbres. It was alien. It wasn’t a “song” with repeating motifs. It was this sonic self-destructive force that would shimmer for 5-10 seconds before collapsing into the next thing. It was like a sonic collage, or an extra-terrestrial radio. Imagine a beautiful pattern mutating into violent nuclear noise, but then it all converges into a tight sliver, a blue highway in dark silent space, that grows forward to the sound of a silky-falsetto-out-of-tune cello, resetting time so a straight 4/4 krautrock beat fades in, with a face popping through the road on every snare hit. It’s impossible to transcribe. The second you think, or the second someone talks, it disappears.

“How is it?” [Short pause. Reaching for words. Cycling through explanations.] “I’m hallucinating music?”

I immediately thought, alright, I need to go to the dispensary and get this exact strain so I can test it in my writing practice. When I enjoyed weed (college and beyond), I typically did it with intention. Similar to how people will have a cup of coffee before a day at the office, I would take a few hits before a 3-hour jam session, or the night before an architectural deadline where I needed a design miracle. All my publishing in the last 3 years (other than this post) have been written and edited sober (as far as I can remember). If I commit to a daily weed habit over the next 3 years, would my craft evolve differently than if I stayed sober?

People are quick to label weed with universal effects. The couch-lock. The auto-munchies. The lazy-poison. To my mother, it’s a “drug,” in the same class as heroin, roach-poison, and Tranq. People will tell you with certainty that weed does this or that, but it’s actually a shape-shifter. The dose, the strain, your age, your health, your genetics, your highly intricate endocannabinoid system that I won’t pretend to understand, your setting, your mindset — these all fuse together to create specific experiences. Meaning, weed is half-chemistry and half-hypnosis. Weed doesn’t inherently breed creative epiphanies, but if that’s your expectation and goal, it might. To the self-suggestible, weed is programmable.

But the chemistry is real, and hard to pin down if your source is some faceless 17-year old who baked an indeterminate amount of weed into an indeterminate amount of butter, and the only data you have on it is the second-hand promise: “this is good shit.” It’s a different world with dispensaries.

I headed to “Union Square Travel Agency,” one of the first places to source weed from New York farms instead of California. The space was surrounded by a construction fence because they’re working on a triple-height “Apple Store for weed” destination. This was the moment the younger version of myself dreamed of. It’s been a long 95 years of weed prohibition, and I’m lucky to have caught the end of it. In “Tales of Beatnick Glory” by Ed Sanders, he writes about police raiding NY poetry cafes in the 50s to arrest artists for marijuana possession. Now here I am, surrounded by helpful pot clerks, branded weed in every consumable form factor you can imagine, light displays, tablets, and credit card machines.

August 15th, 2023 12:07 PM (ET)
Even though I’ve bought weed through a tablet before, this was my first time doing it through a 35” vertical touch screen in my birth state. On the left was an intricate set of filters where I could search by delivery mechanism (flower, wax, edible), potency (20% or 70% THC?), brand, strain, and even effects (”creative,” “focused,” “inspired”). Through an Amazon interface, you get to design your consciousness. I appreciated the control you had over quantity too. I got an 1/8th oz. of Poddy Mouth, a dime page of Sour Glue, a 2 pack of edibles, and 2 loose cans of infused lemonade. Laughably restrained, but since this place isn’t far, I can get low quantities, try different things, log the effects, and build a practice around it. $71.85 total, with $9.34 in taxes. For the price of 1 night of stupid cocktails, I have weeks worth of low-grade mind-altering writing lube.

After that I met up with a writing friend passing through from Milwaukee to Brussels. We had winding talks and winding walks that ended up in a Barnes and Noble; my first time back to a big chain book store since the GPT craze. I took pictures of books, and pictures of tables of books, knowing I could get 180 gists per hour without having to cram my backpack. I did leave with 4 physical books though; books with great prose, short lengths, or daily intervals:

• God Bless You, Mr. Rosewater (a Kurt Vonnegut book, 27 pages in, a riot)

• Be Here Now (source material from the 60s, wisdom rendered in hippy lingo)

• The Daily Stoic (Ryan Holliday)

• Jorge Luis Borges: Collected Fictions

The books cost more than the weed. For under $200, including the train tickets, I went into the city, stocked up on a month’s worth of inspiration, and commuted home. Associating weed with books makes it feel less like a hooligan hobby. The irony is that in high school the codeword for sneaking out to smoke was “going to the library,” except nobody read anything.

Let’s riff about:

• Perception hacks (from waterfalls, visualizers, to James Turrell)

• Weed (legalization, effects on you, in the creative process)

• Bookstores (strategies, in the age of AI, physical vs. digital)

Leave a comment

It’s like I’m a stenographer at the New Circus. I have 7,626 words of fractured cubist prose1 that I need to wrangle into an essay. I probably have 150 excerpts like this that I need to decipher:

July 26th, 2023 9:05 am (ET) —
“Post its on his eyebrows, but half shredded, thousands of curly strings blocking his eyes — “Free the pandas!” — 472 people watching — Head slanted — Seems like a schizophrenic poet around “panda liberation” (?) with a new train of thought every 3 seconds, a possessed oracle — Hands bouncing in a looping motion — 480 — In one hand a finger-strength grip, in the other an Xbox controller. — The crowd is heckling. Mean comments. He speaks calmly: “I am not AI, thank you for the rose” — Red scarf, red shorts on his heads, red bicycle helmet. — Virtual panda gifts flash on the screen (valued at $0.07 each). “STOP SENDING THE PANDAS!” Fake devastation. Face in pain. Pretend anger — 500 people watching — 30k likes — 12x panda emojis = a dramatic 10 second seizure — then, leans in, slowly, and in the deepest voice of Satan, he howls “no more Pandas” — this is torture porn —some guy in Kenya is milking the Internet for its sadism.”

Even though I’m active, analytical, and self-aware through this whole ordeal, I’m not immune to the contact high. The medium is inherently hypnotic. Throughout the day, I’ll catch myself repeating catchphrases like “gang ganggg,” out loud to nobody. “Thank you for the… fuck.” There’s probably a science to this. I’ve been exposed to the Wii theme song2 at least 17 times at a spaced interval, and now it’s looping in my head all day as if I’m in some cartoon lounge. My subconscious is poisoned.

During this TikTok phase, I took up another new hobby of the opposite nature: “GPT-philosophy.” Maybe this is a reaction to my brain getting flooded with soul-deafening noise, but I had the sudden urge to wield a working knowledge of all the best ideas ever thought.

August 1st, 2023 7:29 pm (ET) —
Yesterday I started making a “genealogy of ideas.” I’ll start with one thinker and use GPT to build a foundational knowledge: years alive, main books, main ideas, heroes, influence, etc. My follow-up questions help me link their concepts with the things I already know. Instead of trekking through a dense 300-page philosophy manifesto in old-English prose, I can have a simple conversation to quickly get it. Then I’ll plot them in Miro, connect them to other thinkers, and continue building the map. It’s like a family tree of thought.

I won’t claim that 10 minutes of GPT-noodling will give me a complete understanding of Kierkegaard. That’s not the point here. I’m not looking to become an academic scholar, or to acquire a new lexicon of dense fancy words to sound smart (ie: the determinism of Hegelian dialectics).

I’m a writer. I want to build fuzzy maps of knowledge across every discipline so I can connect them to my own original ideas.

If you search “hilariously wrong maps” on Google, you’ll find something like the map below, drawn by Sebastian Munster in 1569. It’s laughably off compared to the satellite images of today. But it’s close. It has the continents in the right place, some key geographic features, two oceans. It’s a lot better than the previous maps. Above all, it’s useful. I could use this map to sail to Florida, even though they’ve rendered it as a sad nub. If all I have is a proportionally perfect map of Cuba with nothing beyond it’s beaches, I wouldn’t be able to get Florida despite it being next door.

Go wide before you go deep.3

So I built fuzzy maps of ~35 thinkers last week, but there’s one idea I’m going deep on: The Fourth Turning: An American Prophecy. The authors (William Strauss and Neil Howe) didn’t just define and name our modern generations (they coined the phrase “millennials”), they also studied every decade for the last 400 years.

They claim that history isn’t a linear chain of chaotic events. Rather, there’s an invisible cycle of 80-100 years (one human lifetime), with four generational “archetypes” that repeat themselves. Here’s my interpretation of it:

August 5th, 2023 11:43 am (ET) —

“The Golden Spiral of History”

• Gen-I: As we emerge from a crisis, a new world emerges. It’s a new thesis4 on how we should live and organize society.

• Gen-II: There’s a flaw in the new line of thinking, and it triggers a spiritual revolt, the antithesis of Generation 1.

• Gen-III: There’s an attempt to incorporate the new ethos into the original order, and while it leads to an era of brief comfort, it’s ultimately unstable. It’s a false synthesis.

• Gen-IV: We erupt into chaos, polarization, war, and a general feeling of “this is the end.” It’s a crisis, but we emerge from it stronger.

Again, this is a fuzzy but useful model of history. Marshall McLuhan says the only way to deal with information overload is to find patterns that give order to chaos. History is vast.5 We obviously aren’t looping in place, but maybe we’re spiraling outwards according to a pattern, with each cycle becoming larger and more complex.

A model like this is useful for connecting the past, present, and future. Take TikTok. It’s radical novelly, a product of our times. But if history rhymes, have we been here before? In the 1840s, didn’t P.T. Barnum use gimmick marketing to unleash a traveling circus of freaks, outliers, famous opera singers, deformed creatures, and automatons on America? Is TikTok just a traveling circus turned into software? What would Andy Warhol, Ernst Junger, David Foster Wallace, Lewis Mumford, Marshall McLuhan, or Erich Fromm have to say about NPC streamers?

By embodying the minds of great dead thinkers, a writer can channel forgotten wisdom to make sense of weird times.

Let’s riff:

• Who are your favorite writers, artists, and thinkers that I should add to my Miro map? Why?

• What is your stance on going wide vs. going deep?

• Are you convinced that history is cyclical?

• What other historical analogies could help make sense of TikTok?

Leave a comment

Footnotes:

I have the opposite problem. I’m almost embarrassed to admit I spent 50 hours on “Burn Down the Stage.” 2 I diagrammed it in Miro, tortured it with GPT, and retyped it from scratch 5 times. Troubled by “this-is-the-one syndrome,” I even devised an intricate (but aborted) “promotion plan” that involved tricking Elon Musk to boost it.3 I didn’t publish anything else in July because of obsessive perfectionism (someone asked me what I did for work, and I swear I just said, “American Idol.”)

So should you write fast or slow? Do both.4 A fast and easy publishing cadence gives you permission to go slow and deep on other ideas without feeling guilty. The slow work improves the quality of your fast work too.

Basically, I need to start a newsletter.5

“What if you just picked 3 logs from your week, wrote an intro, and wove them together?” This issue is dedicated to .

I felt the hype for Oppenheimer. I heard rumors that it was “devastating.” Given the rise of nuclear paranoia in the last year, I thought this could be a culturally significant film, a modern Frankenstein that would warn our generation on what happens when you sever invention & implementation.6 Did it work?

July 22nd, 2023 5:18 pm (ET) —
Oppenheimer was a great story, with great cinematography, with a few historically good scenes [Trinity test, the speech, Truman’s office, etc.] in an overall mess of a movie. I don’t think Chris Nolan knows what he’s good at. I’m curious to learn more about his process. He’s unquestionably brilliant in some dimensions, but then utterly convoluted and frustrating in others. What is his editing process? Does he get feedback?

Parts of it were transcendent; the peak of what cinema could possibly be. These shining moments lasted ~90 seconds, but they were hidden between long stretches of “who’s that?” and “what did he say?” It’s like Nolan has an incredible voice, but completely missed the shiny dime7 and refused editing. 50% of the movie is a cerebral investigation, and I left emotionally unaffected.8

Leaving the theater, I saw crowds dressed in pink. “Barbenheimer” feels like a cultural resurgence of 1990s mass-media, where everyone gets excited over the same Idols. After not going to the theaters for years, some of us went on back-to-back days last weekend.

The clash between old media (movies) and new media (TikTok) can be felt in this single (stolen) meme by Elon. It’s as if short-form vertical-video destroyed our attention span. A 3 hour movie might feel impossible if you’ve been on TikTok.

The fact that Elon posted an image of PinkyDoll feels like “NPC streaming” went mainstream. Maybe you’ve seen these weird TikTok videos but can’t make sense of them. I decided to dive in. I installed TikTok on my phone and “live-wrote” whatever emerged through the Live feed. After 6 hours last week, I’m burnt out, but oriented. I get it. Here’s a deleted paragraph from “Burn Down the Stage” that will turn into it’s own essay.

July 28th, 2023 2:13 pm (ET) —
“Now in 2023, the weirdest incarnation of the stage has emerged through TikTok Live. There’s a new genre called, “NPC streaming,” where the Idol performs memorized, robotic, (sexual) gestures that correspond to virtual gifts that flash across the screen. The Lurkers can buy things from ice cream cone emojis to AR cowboy hats, ranging from 1 cent to $500, each gift animating the virtual Goddess in a different way. This puts the audience in control. A few thousand people “play” the streamer like an instrument. Like in American Idol, the crowd creates the show, except there’s no longer a 24-hour voting lag; now, the Idol is a digital rag doll, and your clicks can literally move its body. The idol is possessed by a faceless other that is hypnotizing itself, making up to $7,000 per stream.”

I’ve seen weird things, including a man slapping himself in the face 250 times to pay for his wedding.9 It’s hard to believe this is being rolled out to a billion people.10 The blitz pace of a TikTok feed probably does something to our culture’s sense of patience. Compare this new form of media to baseball; the boring sport, the country’s past-time. In 1946, 13% of the country went to a baseball game, and now, 20% of the country is on TikTok. I went to a game two weekends ago, the day after NPC streaming emerged.

July 14th, 2023 6:20 pm (ET) —
The beer hustlers, the chanting teenagers, the yellow vested security guards. The rumble of trains and stampedes. A sizable portion of the New York population collectively agrees to shuffle over to CitiField despite the lousy season and grim shot at the playoffs. This is a means of mass leisure, physical leisure. It’s inter-generational fun; the divine relief of spectating, to turn off and have no consequence, to blur out on left-field IPAs and convince yourself you’re connecting with the past times of your childhood and country. Baseball is the last battalion of patience in 2023.

Some people question if baseball will survive into the 2030s.11 I think the pace is refreshing. Really focusing on a game is almost meditative. This sport was the anchor of my childhood, and I want to write an essay that reveals the hidden wonder and mythology behind what seems boring and confusing on the surface.12

Some essays I liked last week by , , and

The Intronaut

The Community of Kansas City

This essay was difficult, time-consuming, and a joy to write. It’s an homage to home — to unbeatable barbecue and the feeling of a summer day at The K. (If you’re a ball fan, read this on my website for the best experience. There, I embedded highlights from the game…

Read more

3 years ago · 8 likes · 8 comments · Garrett Kincaid

The Creativity Gap

Genius is voluntary insanity, not a high IQ

I'm standing backstage, wiggling my mouth to make sure the fake mustache on my face isn't going to come loose. My friend is wearing a wig that you'd probably call a "Karen" haircut. She's going to play the disaffected wife to my idiot husband. For now, though, her expression is anything but disaffected. I see primal human fear in her eyes…

Read more

3 years ago · 9 likes · 11 comments

Sunday Candy

Trivial Treasures

I feel a responsibility. To bring attention to the commonplace by weaving words, to capture the heart of the ordinary, imbuing it with reverence. To be, almost an ambassador of the ordinary, challenging what is valuable, and cultivating an appreciation for the seemingly simple…

Read more

3 years ago · 12 likes · 5 comments · Sandra Yvonne

Let’s riff:

• What did you think of Oppenheimer?

• Have you been on TikTok Live?

• What is your least favorite thing about baseball?

Leave a comment

See you next week.

Michael Dean (Logs, Substack)

Footnotes:

I started this on December 9th, 2021, and have averaged 15 posts a day (~1,000 words), separate from my published essays.

I’m inspired by the first online writers who built HTML-sites from 1993 to 1998, before Xanga, OpenDiary, and the wave of platforms that simplified online-writing. Writers like Justin Hall and Gus Mueller saw self-publishing as a revolution; an opportunity to pour their consciousness into the Internet in real-time. They were scrappy, prolific, unedited, and unfiltered; embodying Kerouac’s spirit of “On the Road,” but native to the Internet. Their websites feel like mazes; endless rabbit-holes through the neurons of some strangers psyche.

What I’m doing here is an extreme form of “ambient capture.” It’s a practice of capturing thoughts immediately as they occur. I used to privately jot down frantic, illegible notes to remember things, but since logloglog is on my public site, I’ve been capturing my ideas in semi-coherent prose. It’s a game-changer.

Over the last ten years I’ve cycled through dozens of idea-capture systems. Logloglog has been the most fun, the easiest to maintain, and it’s what I would recommend for anyone who is interested in creating. Many of the note-taking philosophies in the productivity space can resort in a tinker-fest (I’ve been there). They emphasize collecting external “bricks” (articles, links, and highlights), and then over-organizing them in private, with the hope that colliding the right inputs will usher in a higher quality or quantity of outputs.

In the last 50 days I’ve undergone a shift in how I collect ideas:

• From private **to public;

• From external to internal thoughts;

• From chicken-scratch to prose;

• From a systems architecture to a daily page;

First, I’ll unpack the value I’ve found from capturing ideas in this way. Then, I’ll address how the tools we have for expressing and sharing ideas (Twitter) fall short at authentic expression, and why we need new ones.

The value in logloglog

1. Catharsis - Putting thoughts down on paper is easy therapy. Any thought that bounces around your head, good or bad, takes up mental bandwidth. Writing is a release valve. In Julia Cameron’s “morning pages” routine, she explains how “dumping” has value in itself, even if you never return to re-read it.

2. Eruption - It is liberating to write in a format that encourages fragments. Since there are no length-constraints or title-requirements, an idea can express itself as a sentence, a paragraph, or an accidental essay draft. The collage-like nature of this format reduces the demand for structure and “linear coherence.” This gives the writer permission to follow their curiosity.

3. Mindfulness - A real-time capture log implies that your own life is the best source for inspiration; not feeds, articles, or encyclopedias. Having a public log changes how I see the world. Every moment, experience, and conversation is an opportunity. This practice cultivates self-awareness. As interesting thoughts arise through the day, I have to notice them happening, and then have the discipline to record them. I dip into logloglog frequently, and it acts as an interstitial journal.

4. Memory - It’s fascinating to jump back to a random day in the past and relive my full train of thought. This practice is a method of freezing consciousness and preserving it for the future. It’s more than a morning journal; it’s a change-log of my consciousness; a real-time autobiography. The prose I write controls how my future self will remember the current phase of my life.

5. Self-knowledge - You can learn a lot about yourself by retroactively looking through the things that were on your mind. When you capture everything crossing your mind, you get an honest reflection of the landscape within. It’s not a niche; it’s the true, multi-faceted self, rendered as a mosaic. You’ll find patterns about yourself that were impossible to see in the moment. Here’s a word cloud showing the range of concepts that emerged in the first 50 days. Each of these had over 15 mentions. [re-import word cloud]

6. Simplicity - It’s easy to maintain a note-taking system when there is minimal overhead. There’s no process to categorize or link blocks. The priority is to capture thoughts that matter, and to write them well. It only takes me 10 minutes each morning to read through the past day’s log, pluck out the worthy ideas, and archive the rest. The whole system is basically a text-file per day. Sometimes lo-fi works.

7. Social - It feels good when others acknowledge things in your log, or even take action off a note that seemed unimportant. My log has sparked conversations, book purchases, and changes in the daily routine in others. This could theoretically happen on Twitter, but people share such filtered version of themselves in public forums.

8. Momentum - There are some people who check my site and read through my log every day. That fact alone motivates me to never miss a day. It keeps me accountable and wanting to continue the streak. The longer I go, the less likely I am to stop. It’s motivating to know that I’ll have a whole archive of notes that document my life. It’ll be something my kids and I can look back on in the future.

9. Practice - Every next note I create might be the first and only note that a new reader stumbles upon. It forces me to write in semi-coherent prose. There are two great side-effects of this. At a functional level, it means my future self will be able to make sense of what my past self was trying to say. At a craft level, it means I get to practice writing in prose, a lot. In 1 month, I write as much prose as I would’ve in 4 months of essay writing.

10. Seeds - It’s feels good that tweets and essays are accidentally created during the process of transcribing my life. Each morning, I read through my log, and find that 20-30% of what I’ve captured are seeds that can grow into Tweets or Essays. Additionally, I can search any phrase, and find all past references to it, as well as the context for when that idea occurred. I don’t have a shortage of writing material, I have an abundance.

[Note: This essay was assembled from ~30 notes I surfaced from the last 50 days. It made writing this pretty easy.]

Twitter vs. Notion

Michael, this all sounds great, but why don’t you just do this on Twitter? I tried it. I’m inspired by @visakahnv’s approach. I set up an alt-community with some friends and posted 50 tweets a day for a short while. Aside from the social benefits, it was way less enjoyable to actually generate ideas from within Twitter. There were a few that were deal-breakers.

• Bloat: I was hit with advertisements and algorithmic suggestions.

• Distraction: It was easy to get hooked back into feed-scrolling.

• Constraints: Forcing to think in 280-character chunks was choppy.

• Non-editable: Unable to refine and expand on thoughts.

• Templates: No control over how I displayed my body of work.

• Drafts-inbox: The UI to manage a queue of ideas it terrible.

It’s been great using Notion as a place to host logloglog, but it’s not without it’s flaws. My experience with Notion (and my discipline around systems in general) makes it feasible for me to capture within Notion, but others might struggle with it.

• It’s a manual process to review posts & create Date blocks

• Each post isn’t an intelligent database object with properties

• There’s high friction to add images, video, and audio.

• It’s not easy to clip text into the open blog format

After doing logloglog for 50 days, I think it could be valuable for anyone who does it. But there just isn’t a great tool that removes all the friction from the process. I’ve been meeting with Duck and Syslog every week to jam around some of these ideas. They’ve each been making some slick prototypes, and it seems this project is gaining a bit of momentum.

A new capture app

While this is mostly an experiment in capture for now, it’s origins lie in discussions around identity and social media. I’ll be adding more essays to the Streams tag over time. To summarize the issue:

The toxic nature of social media is a result of the “social graph,” which has gone unchanged from MySpace through TikTok. By connecting everyone 1:1 as atomic individuals, and broadcasting ideas in feeds, it turns Twitter into a game of American Idol. These networks don’t reflect human nature. People are multi-dimensional beings, and express different facets in different contexts, but social media doesn’t acknowledge this. It creates a culture of celebrities and consumers.

The driving questions here: how do you actually turn consumers into creators? Then, once people are expressing the full range of their psyche, how do you authentically connect people and strangers around these shared interests?

There are three general problems we’ve been orbiting around:

Create the best capture experience; one that is simple, feels good, has compounding benefits over time, and can be used as a primary form of information and data storage. A “Captain’s Log” style app could unify text, audio, pictures, and video within a daily block system.

A simple experience to assign ideas to a Stream; is there a way to gamify systems maintenance? Instead of having Inboxes to purge, what if there were a Tinder-like system to review your past original ideas? You could swipe-left to archive ideas, or swipe-right to push them to one of your Streams. It’s a type of spaced repetition.

Connect with others around Streams; instead of bulk subscribing to someone’s newsletter or social profile, what if you could connect with specific facets of them? Instead of being pinged with real-time Slack-like notification, what if every user had control over a Digest that featured the Streams they’re subscribed to?

If any of this interests you, shoot me an email.

Michael