michael-dean-k/

Sometimes the coolest website is the least readable.¹

I recently came across gwern.net and quickly sensed it would be a personal-website-as-labyrinth that I'll venture into for weeks. It has an alien feel to it, or at least foreign relative to the optimized and foolproof UIs you find across templated social networks. He is a Wikipedia editor with 34,569 edits (on English Wikipedia as of 6/1/26) and so naturally his personal website is a personal wiki, documenting his self, his site, his links, his tech stack and writing, each adorned with hierarchical outlines on the left (1, 1.2, 1.2.6, ... ). I sense him to be something of a techno-Montaignean, capturing his mind and culture, interweaving quotes, and pseudonymously appearing on the Dwarkesh podcast as a real-time avatar.

So yes, lots of diving and mapping to do, but I need to note one observation of my experience here, which I want to be careful not to recreate on my own site. Most of my time is spent marveling at the structure and navigating what exists, but I'm presented with so many hyperlinks that I can rarely ever focus on and absorb a single page. There are 53 links in my current view. Maybe I'm exposing myself as someone who reads linear essays a lot more than I read Wikipedia articles.

I suppose there are two ways to know a person, in breadth and in depth. Technically this site has both; once you wade through the peculiar structures and get a gestalt of the person, you do find linear essays that are well written. But even those are nested in scaffolding; 60% of the opening view is dedicated to metadata: nav links, title, tags, a summary, ratings of completion, certainty, and importance, links to similar notes and a bibliography (many of which, if clicked, opens a pop-up with more information), and then an opening quote, all before the opening sentence.

Even if I think this meta-data is misplaced, I personally love having it all accessible. I get frustrated by a popular online writer (/marketer) who refuses to date the essays on his website, probably from the thought that datelessness is timelessness, or the fear that the median reader will see something dated 2019 and think ugh, that's old, and click away. Marketers want a simplicity that's legible at scale; I am a complexophile. A personal website (or anything, really) should be as dense as can be contained, for that gives the super-reader the ability to grok you at a resolution closer to reality, but only as long as it can be progressively revealed, giving the first encounter an on ramp into the beast.

I'm now arriving at what I think I believe: if your website contains a collection of essays, then drop the reader directly into prose, and withhold structure until the end of an experience. "Prose before portals" could be a simple, multi-scale maxim. A standalone essay page should have a header of only 15% metadata, and even the frontpage, instead of providing a traditional orientation, could drop you directly into a stream of recent essays (a design decision I haven't committed to yet, but am leaning towards). Perhaps portals could exist minimally at the beginning, but maximally at the end. An essay's footer should be entirely portals.

Another debatable decision is that an essay should rarely include internal hyperlinks. Contrast this to Justin Hall's links.net of the mid-90s, whose whole website was a hyperlink maze. Gwern's site, much like Wikipedia, is also maze-like. These are conceptually neat, and of course native to the Internet, but I always catch myself skimming rather than reading deeply. I am astonished at the size and grandeur of the park, but I am distracted. Essays demand depth. My ideal would be to fuse the medium of physical reading with the navigation of the web: uninterrupted prose, bookended by optionality. Maybe you could refer to this as "extrastitial" instead of "interstitial": the internal modules aren't connected, but the wholes are connected end-to-end. (This actually mirrors how ChristopherAlexander structures his chapters in A Pattern Language, the original wiki: the beginning and end points out to other chapters, but the body is uninterrupted.)

A final note on skimming: I catch myself doing "Inspectional Reading" a lot here, the second level of Adler's How to Read a Book. There are many possible causes for this. To start, it could just be my fault: right now I'm reading as I write this essay, and I have much to do this morning, and so to some degree I'm reading to the level that it enables me to write, for if I read everything full, all the tabs, I could become absorbed for hours and get nothing else done before it's time to watch my 5-month-old daughter for the rest of the day. But aside from self-blame, there's a FOMO that comes with any thriving website: when you're aware of a sprawling network of high-quality information, it becomes hard to sink into any one piece because you're too aware of what you're missing. And so there might be something to intentional concealment and revelation.

I want a reader to come to my site and experience flow, not analysis paralysis, but this opens a new question. Who is a personal website for? The answer is in the name. The reason I'm shifting from Substack back to a site of my own is because I want to write in a place where I set the rules. And so there's a risk of leaning too far into becoming a self-archivist, where I try to convey to you the totality of myself, the full hyper-object, instead of letting you compile me one file at at time. If the full extents of my writing are something like a national park, I need to make sure you get on the curated trails and experience nature, instead of presenting you a network of maps.

Ironically the first essay I read by Gwern was on Tools for Thought, a wonderful takedown or Rome, Zettlekasten, and networked thought:

"Most people simply have no need for lots of half-formed ideas, random lists of research papers, and so on. This is what people always miss about “Zettelkasten”: are you writing a book? Are you a historian or Teutonic scholar like Niklas Luhmann? Do you publish a dozen papers a year? Are you the 1% of the 1%? No? Then why do you think you need a Zettelkasten?"

A rule I've had to set for myself is to never link my notes; they should live scattered in an epiphany swamp of atomic ramblings, only to be given name, date, and tag at the moment of publishing. Most won't make it out of the swamp. So many writers suffocate themself in PKM hell; instead they should open the pipeline to get finished prosed onto their website. And now, I find myself reaching for heuristics on how to present essays, a whole body of work, and the very self behind it. I think there are similar risks with public hyperlinked structures, along with ways to let the atomic nodes of a network speak for themselves, without severing from the hive.

This is all just first wind from second impressions, but as I understand Gwern more deeply and build out my new site—after existing only on Substack for 3.5 years—, I'm sure I'll come away with something useful.

1. As a writer needs a site of one's own, a place designed for their particular psychology so they can be the most prolific, honest, adventurous version of themselves. Solitude is important. Montaigne, the founder of the essay, wrote up in his tower for a decade. When you are your own audience, your practice is self-justifying. You are intrinsically fulfilled, and do it regardless of validation, growth, or revenue. To become self-validating is to become a nuclear engine of creativity. When you write on your own site, chances are you will spend much time on ideas that no one will read. That's inefficient, but essays are inefficient. I need to ruthlessly follow what matters to me, with no fear of being illegible or invisible to others.
2. That said, you can and should invite others into your garage. I still plan to keep my Substack and post there, but it will be more like a newsletter, a digest of the controlled explosions happening in my own neighborhood. I do believe in the value, even, the responsibility, of writing in public. By making your place tidy enough for friends, strangers, students, customers, mentors, heroes, whoever, to come in, it makes you put an extra oomph in your crafting of language, and it creates seeds from which relationships can grow. When you have visitors in your territory, they play by your own rules, so you're generally safe from mobs and barbarians. They will not trample over your furniture and throw the books from your shelf like they would in the town square.
3. In 2023, I was hopeful that Substack could be an all-in-one platform—a website/newsletter/discovery engine—but it has heavily shifted into an app-centric social media platform. The app starts you off in an endless, algorithmic, engagement-ranked feed, and the design has slowly evolved to trap you in the app. When you click in article, the default URL is the Substack one. When you click into a person, you can't even go to their site anymore; you can only view them through their profile template. This means all the customization and self-archiving and mythologizing that goes into your site is off limits to the app, the thing they're trying to corrall attention through.
4. I'm very allergic to "Substack is dead" posts, and most of the critique is often a projection of their own weaknesses (ie: when people naturally stop growing, it's easy to blame the algorithm than to take responsibility for it). In my case, the Substack algorithm has worked pretty well over the last two years, and I'd be stupid to abandon it. But the whole system has limited my intrinsic passion to write, and that matters more, enough that I'm willing to take the risk with a split publishing system: Substack newsletters that link out to my site.
5. Back in 2020, a Write of Passage concept was the "public to private bridge," meaning you find people in social media feeds, but then redirect them back to a place of your own. Now that Substack is mostly a social media network, I think that same strategy applies. It's not where I want to host my essays anymore. I'll host newsletters and paid content there, but the timeless stuff wants to live in a place that is timeless.
6. If you have a portfolio of writing, Substack feels like a pretty bad way to make your old work legible, especially within the app. There are no tags or sections. No about page. No navigation system. No ability to frame call to actions as visually dominant. The beauty of your website, especially if you build it from local markdown files, is (1) you have a single source of truth for all your writing, and (2) you can just respawn new interface and navigation systems as your portfolio evolves.
7. Even though Substack lets you export your essays, it's really more like a failsafe, a backup incase you ever decide to leave. Of course, it's very nice to have that! But it's still a cloud-based system, where editing your past files is slow and clunky, and you have limited ability to point your essays elsewhere. When I have a local folder of my essays, I can very easily spin up a stylized website around any essay, or any group of essays (say, for example, if I'm making a proposal and I want to curate a handful of essays. I can point my AI at any combination of files and folders for context.

What would a 3D essay look or feel like? The "video essay" is a format, but that's really more like a performed/spoken essay with picture and video over it. I'm curious what it could be if we keep reading prose as the core mode.

Here's a prototype where scrolling brings you in instead of down. Instead of feeling like you're just reading a wall of text, it feels like you're moving forward into a series of spaces.

This breaks the essay into paragraph blocks, where you only see one at a time, which works something like focus mode (and I suppose there could be a way where you could preview the paragraphs behind and ahead). There's opportunity for each paragraph to have unique color, imagery, a distinct vibe to match the content. Additionally, each paragraph can have portals to jet out from this essay into different ones, making it something like a choose your own adventure.

Is anything gained from this? Or is it just a novelty? Best case, it's a new medium to bring prose into the short-form video era; it's much less intimidating to be presented with a single screen of text than a whole wall of it.

My personal website is “out of the bag.” Meaning, it’s not a private thing shared among 3-5 friends anymore; I excitedly shared it with Essay Club yesterday (60 people or so). I am leaking it prematurely because of the giddy hope, that personal websites are the new paradigm for writers, an escape from the enshittified commons. But I have to admit that I haven’t thought through two important questions yet, so here it goes:

1) Does this kill discovery?

If I were to instead publish all my ideas in real-time on Substack notes, would my audience grow more? Probably. The reality is we all self-censor ourselves in public feeds, in a thousand different ways, so it’s not like all of this could naturally emerge in feed. I tried this in January. I killed my logging practice with the goal of trying to just do it all on Notes. For two weeks, I was able to post spontaneously, but I find that if you ever stop momentum, it’s very hard to get back out of your head and into that groove. Overall, I just wrote less. I wonder if there’s truth to the idea that all writing practices grow/incubate/evolve better in semi-public spaces. It’s not that you should ignore the occasional blast. It’s that there’s a natural progression of nurturing ideas.

Another angle is, “I’m not interested in audience growth,” which is true because it’s not motivating for me, but I am in several ways entangled by growth, meaning, a complete lack of growth could threaten the sustainability of my writing. And so a middle ground is to incubate on my website and then selectively drip ideas through notes and newsletters. I could do a weekly or bi-weekly digest, Austin Kleon-style (“10 logs from last week” + essay visualization + updates, etc.). Not as sure how I would do it on Notes. Daily? Sporadically? Something else? Either way, this brings back the whole "public-to-private bridge" concept from Write of Passage. I think some people abandoned websites and just accepted the feeds. I know in 2023 I shifted entirely to Substack thinking it could be my entire digital home, but now it feels like rented land.

So my website gets maybe an A- in unlocking my writing practice, but only a C in growth, but maybe it’s a B in conversion? As in, if someone spends a lot of time on my site (and people have told me they’ve spent hours in my logs), they’re more likely to trust me—due to the sprawling, unoptimized, honest nature of things—and more likely to get a paid subscription or join Essay Club? Unexpectedly, personal writing could be a more honest and more effective form of “marketing” than strategic value-focused content (“Are you in hell? Well I’ve got the thing for you…”).

2) Is there risk in having all my ideas public?

Now that I’m in my own place, relatively unchained, saying what I want, and reading and writing about political science a bit more (I have a draft comparing Karp’s Technorepublic to Leviathan by Hobbes), I’m a bit paranoid to share ideas so openly. It’s hard to imagine facing any real-life consequences for the words I write; I’m just a nobody! It feels hubristic to think that I’d be considered a threat to the state for my thinking, but maybe these thoughts are natural, considering we’re being pleaded to accept an AI-powered surveillance state in exchange for security. (It's not that I think any of my writing is particularly rogue, but let's say I start thinking through a scheme to organize a million swing state voters to rally around a single-issue voting boycott in order to pass a bill on election campaign reform, you can see how democratic ideas might seem threatening to a state.)

It’s effortless for a state agency to scrape the Internet, build psychographic profiles on its citizens, and give them a “loyalty score.” Let’s imagine they also have an “influence score” too, determining how much sway you have over your citizens. If you have medium levels of loyalty and influence, you’re probably not being actively monitored; but if you have extremely low loyalty (L=5/100), it’s a threat even if you’re low influence (I=0) because you might be a terrorist; but also if you have extremely high influence (I=95), and even slight disloyalty (L=45), then that’s a risk too. And if it’s not the state absorbing my context, it could be independent actors scraping my site to clone me and do what they will…

I guess the point is that AI creates such a leverage over information, that you’re own personal data becomes extremely valuable. It can be leveraged not just by you, but anyone who has it. A personal website of an unfiltered nature is a higher-resolution signal than a social media profile where most interactions are shallow.

Grasping at a solution_

If all these concerns are justified (and maybe they’re not), then what are the practical methods of maintaining privacy? I’ve already written ideas about security gates and embedding-based encryption, and that’s all technologically neat, but it creates friction for the readers! Maybe that’s okay? But then this ignores the “entangled with growth” constraint from above…

And so maybe the Third and only way through is to make the encryption solution that is both an alluring and enjoyable UX for the reader.

This starts by understanding how websites get scraped, building solutions to avoid it, and then shaping them to be reader-first. You can only really do this by scraping yourself. I’ve scraped full portfolios from Substack in two different ways, and even a decade’s worth of Marginal Revolution posts. At a minimum this means avoiding RSS and HTML, which this (current) site already violates (ie: it’s ideally on a server and requires permissions to load).

Scrapers can prevent against automated gathering; but not against a person or agency that has already found your site and is willing to sit through slower and manual methods to extract information. A defense here would require gating and admin approval, another hinderance. There is something here about taking monetization dynamics (paywalls) but reinventing them for privacy’s sake. Maybe the way around this is to only encrypt a portion of the content, say 50%, with cryptic previews of what lies beyond (either through titles or redactions or chaos).

To try to synthesize this all together, what if a website were a video game?

Website as gamified maze?

As smart as today’s AI’s are, they still can’t beat Pokemon. They can transform text and code better than the world’s best engineers, but if you ask them to navigate an environment where vision and long-term memory are required, they bomb. Pokemon has very simple inputs too: 4 navigational directions and then a Click/Cancel boolean. If you were to make it more challenging, with inputs that required hand-eye coordination, that could solve two problems: it scrambles existing scrapers, and creates a novel UX.

I also sense there’s something to turning a website into a literal maze, not just an overwhelming sprawl of hyperlinks, but an actual video game you have to navigate through (it would be neat if somehow notes were semantically distributed across a map so there are “towns” of ideas). Can friction be made gamified, exploratory, enjoyable? Maybe it’s not only a matter of walking around, but solving puzzles/riddles at gates to advance deeper into the labyrinth to find more sensitive ideas. Maybe some gates require passphrases, or interactions with me. There could even be a minotaur at the center who holds my deepest memories, aspirations, and fears and if you can kill the Minotaur you get the passphrase to my Bitcoin wallet.

I was able to launch this website in <15 minutes. The setup is local and simple. I have a /writing file in my Obsidian vault, and then subfolders for /code, /publish, /working. /Code holds the site design, /publish my archive, and /working files have .gitignore to not push templates and notes and such. Claude Code handles the website, and different skills help me manage tags, do the menial ops stuff, and push to the Internet. All I have to do is sync a single folder to Github, and the changes are live (hosted on Netlify for free).

Compare this with my first website prototype. I was endlessly iterating on designs and fonts, and thought that I had to organize, filter, and polish my five year archive before I could get started. Probably spent hours on it before burning out on the haul. With this second version, the principle is essentially, "if it doesn't immediately produce something of long-term value, it's not worth systematizing." Now the approach is to move forward here, and slowly fill in the backlog as I'm inspired.

No need to widely share this yet. I'll make little changes day-by-day until it becomes my main place. So many things to consider. For example, I decided to add an initial on the name ("michael-dean-k"), but without hyphens ("michaeldeank"), my wife confused me with "Michael Dank."

Screens are unfairly tainted. I'd love to write a post about how screens are underrated, a glorious technology that would be marveled at by basically any other generation in history. Screens are the scapegoat because they are the point-of-contact, the portal through which bad or selfish actors bend your pixels to their whims. I know people lament over "blue light" and the physical strain from staring at something for many hours, and of course that is real at excessive doses, but might that then be an software or psychology issue?

The main reason I started writing this was to riff on screen-time with kids. There is a revealing nuance in the advice, "no screen time for kids below 2 years old, but FaceTime with relatives is fine." Why is that? It's not the screen, but the nature of what's on them. FaceTime is fine because there is a fixed and unchanging frame which features a fixed and unchanging person moving within. There is stability and coherence. We take this for granted, but infants haven't modeled this yet! They might not even have object permanence (ie: if they disappear from the frame, are they gone forever?). So by this logic, any piece of media with a stable frame is potentially infant safe; beyond FaceTime that includes single-shot lectures, text editors, etc. Obviously an infant will not be in gDocs, but the point is, if they see you using a static interface, there is little harm, it's simply another object in their environment.

By contrast, cartoons and commercials are the real issue. To explain this to my mother-in-law, I counted out loud the camera cuts in an ad, and it's less than once per second. There is a whole psychology on why they do this, which I can guess, but should probably look into. TLDR you are being addled. But when an infant sees this, I imagine the frame resets are alluring, but disorienting. If the frame changes every second, they're locked trying to make sense of this self-evolving landscape, an experience novel and atypical from every other thing they've seen. It has no continuity.

By this logic, it also explains why feeds are worse than personal websites. You just stream past 100 things per second and have no steady frame. Even though my site is feedish now, it's all from a single person, so at least that's a constant. I'd feel okay with my daughter at 5-years old reading personal websites and having her own, but I wouldn't want her to be using algorithmic social media feeds even at age 15.

I have some neat prototypes for a personal website, but now I actually want to build a stable backend, one that can serve me for 5-10 years, or more (100-year hosting would be ideal), and persist among many different UI or platform changes. This means I’m trying to think forward to where the Internet could be by then. This involves extrapolating a current trend to its extremes, and even if you don’t know for sure it will happen, it’s good to have comfort in knowing you’re protected from extreme edge cases.

The one top of mind is the death of the open Internet. This goes way further than “the dead Internet theory” which only covers the proliferation of bots and slop. This is about bad actors being so leveraged that it becomes dangerous to have any public content of yourself, in text, image, video, or audio. ie: Any hacker or frenemy can clone you and do what they will. Or maybe a rogue government can analyze your psyche and determine your "loyalty score" is only 35% and shadow ban you from getting a mortgage. I will not get into specifics here of the likelihood of different cloning, phishing, or surveillance schemes, because all that does little but bring you to madness, but my point is that if you want your website to be a 5 million word 1:1 representation of your mind (in all it's vulnerability), it's worth designing for the most paranoid future possible (like how engineers design bridges for earthquakes that will likely never happen).

One response to all this is cyber-defense. At the absolute minimum, this means locking most things behind a gate where only the approved can get through. A more clever, technical solution is to share encrypted “coordinates” that represent the semantic nature of an essay, and then let people surf through prompting and approval gates. An even more extreme idea is a mostly-private site with a kill switch, which involves (a) signing in once per month to mark "I'm alive," and also (b) giving my wife a secret key to type in when I die, which then releases all private material. Obviously this throttles reach, but isn’t there psychological value to limiting your audience anyway? Montaigne wrote alone in a tower for a decade, and so if the approach is to use writing to steer you life and mind, at the detriment of audience growth, then this might be the way to go: a literary labyrinth accessible to maybe your 30 closest friends and anyone else via application who can prove they are not a ghoul.

The other alternative is to embrace the weirdness, that no matter what, we will all be rendered through a schizophrenia filter, with no choice but to relinquish control over the non-canonical or rogue versions of ourselves.

I’ve been reflecting on how my writing will change once I have a newborn, and I keep coming back to this idea of releasing a “monthly EP of essay demos.” This means that I’ll send a post with 5-10 links to other essays that I “ghost posted” (publish without sending) earlier in the month.

I currently only have the S and L lanes of writing working. Either it’s a 2-minute log or a 20-hour essay. The goal is to prioritize the M (medium) lane, a 2-hour essay; instead of sending them out in real-time, I’ll batch them and let readers click into the topics they want. Feels like a strategy to be more divergent, more experimental, less formal, without overwhelming people and confusing them from the core mission of Essay Architecture.

I had Coco read through a week of my logs, and she shared three patterns she’d want to read more of: (1) unique, vulnerable experiences that show conflict and inner struggle; (2) lens on for self-improvement regarding life or writing; (3) culture commentary that helps make sense of big ideas. She was less interested in technical topics, or hypothetical scenarios (such as trying to imagine the handicap we’d have to give tennis pro Carlos Alcaraz for us to have a competitive match in tennis). The beauty of the EP strategy is that it gives readers a menu, and each will have their preferences.