michael-dean-k/

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.

Something about hyper-logging (capturing your mind in prose) feels desacralized when I see it as the grown-up development/extension of my AIM bio, or my original Facebook bio (which had a whole series of categories, like favorite movies, books, etc.). Why keep an extremely detailed and public log of my self and thoughts? I guess I see it like a change log of my evolving identity. That was sort of Montaigne's whole thing (perpetually in transit). I imagine the norm is to burrow into your shell of self for as long as possible, to avoid the confusion of drift, but I try to harbor a non-static self. I feel a cringe in sharing this self-congratulations. There's the tension.

I think I'm doing an irregular thing by obsessively documenting thoughts, and from my own perspective it does feel like I'm continuously evolving, but an outer perspective might see this as nothing more than a frivolous blog. It's likely that my whole arc is illegible. Some degree of it comes to surface, like my ever-shifting "career," but most of how any of us feel, think, and change is illegible to each other, except in extreme rare cases of friendship, and so the more idiosyncratic your path, the less anyone can understand you.

I suppose my logs could function as a private journal, but it would lose an important quality. While, there are some consequences of writing in public (a subtle self-censorship), there's something more important you gain: the stakes of knowing that your work could be read in the future, if not by a friend or stranger, then at least a future version of yourself. Whoever it is, if they care to spend the time to read, they would understand you more than probably anyone in your life. That slight pressure snaps me into a mode where I try to be coherent, articulate, and sometimes expressive. When I look back at my old chicken scratch journals, I almost always skim and skip and hate it. But when there's a slight care in crafting the language of my thoughts, it becomes something that outlives the moment.

And so if public writing comes with self-censorship, and private writing comes with a lack of stakes, then the way to go is semi-public publishing. It gives you both freedom and stakes. You won't grow your audience this way, but I think you will forge a sense of self and voice that you can bring with you when you try to build an audience, but that's really secondary. It's the self and voice that matters.

My core value is contradiction, for there’s no other trait that leads to freer-thinking. If you are so stable in your beliefs, you run on auto-pilot. But if you are a Christian atheist, a Luddite technologist, a scrappy perfectionist, or any other kind of walking-paradox, a legless man, then you really have some explaining to do. In resolving the conditions between the two true but opposite things you harbor in one body, you think to make sense, and write to speak truth. This is where you find the work that matters. 

Why am I so inspired by the reckless and irresponsible Neal Cassady? It will take me years to find that out, if ever, but in that pursuit I invent some value system that is uniquely my own. This sort of embrace is, by the way, brand suicide. Your consumers are slow to update their mental model of you, and in the high-speed pizza counters of the Internet there is only small talk and one identity per person. To write for a niche, to stay on brand, to hit the same message, to do the things required for you to dominate the soul-gutting mediasphere is to mistake banal desperation for your alien soul. Do not trade oneiromancy for efficiency. Do not have one mind across all essays, let alone in one essay.

The value of playing an infinite game is that when you follow your passion, you move according to a compass that is cryptic to the outside world. You will make decisions that won’t be rationalized/justified by VCs. For example, I still want to be an “essayist” more than a “founder,” and that might confuse business-minded folk I engage with. But if I’m an essayist my whole life, then I’ll be constantly improving and sharing my own composition tech-stack.

"Conditional identity" is the idea that the self is a construction of nested if statements. You can’t accurately describes yourself through a series of variables (“I am kind, fearful, Orthodox, etc.”). Every attribute depends on circumstance. If X, I do this, but if Y I do that. Maybe this sounds obvious, but when you take this seriously, you realize that you behold opposing beliefs that can’t possibly go together. When you embody conditional identity, it’s impossible to be “open-minded” without realizing that you are also its inversion, depending on context.

I wonder if the main bug in the human OS is that there are psychological and sociological incentives to define yourself through variables instead of functions.

You save glucose by automating your thinking. The process of self-discovery requires you to retarget your CPU to optimize its own code (instead of processing incoming tasks with cached CSS). It requires a real-time awareness to re-evaluate your identity logic in every new contexts. It’s tiring, but it’s rewarding.

Socially, it’s hard to have tribal meme wars with conditional identity. If you say, “typically I believe in X, Y, Z, however if A is big enough problem, that I will consider L, M, N, O, P, but if that crosses a threshold D%, then I’ll default to F until it collapses,” it’s much harder for the pack to know whether to welcome or kill you. To fill in these variables, that might look something like “typically I’m libertarian, but if shadow power conglomerates, I’m open to a transparent authoritarianism so long as it’s deployed on a public blockchain.” That is a salad of contradictions unless you really dig into it. It takes far less bandwidth to process “I”m a Democrat,” or “I’m a Christian,” but while cached thinking is convenient, it severs you from reality, and from the solutions needed for complex problems.

On the Internet, everyone judges you through split-second impressions, and there’s no time for them to work through your nuanced takes. You have a choice: to be understood as a false idol, or to be misunderstood as your true self. While there are ways to turn yourself into a 64-bit self without feeling too phony, I think the real lasting work comes from knowing yourself, which means being okay living in realms of paradox, ambiguity, and burdensome complexity.

I think the key reframe here is to not see the uncertainty of conditional identity as a source of fear, paralysis, and alienation, but as the only place where you sit at the edge of becoming.

Soda bottle and startups need to be hyper legible, but humans are inherently illegible: multi-faceted, contradictory, complex. In a lot of ways, the medium of the Internet requires you to be hyper legible. But I think there’s an interesting paradox where you can be both. You can simultaneously pass the 10-second test before someone subscribes, but then you can offer a cavern of complexity that some choose to wander through. If you’re over-optimized for marketing, you risk becoming over-optimized, perpetually delivering on an old, stale promise. Instead, you can set the expectation to break expectations.

Pretentious > pre-tense > context (I realize this is a stretch, but...). Artists are pretentious when they’re frustrated that others don’t have the context to understand what they’ve made. They’re upstream of culture, and so others don’t have the framing to pick up on it yet. There are two reactions, 1) not caring if they get it, and 2) making work for mass contexts (meeting the culture where the OS currently is)—and maybe both are wrong.

Instead, progressive ideas come with the responsibility to make sure anyone is equipped to download the context to get it. The trick is doing this implicitly without being too on the nose. The bootloader has to be secretly encoded. Deconstructing your own lyrics feels too desperate. Maybe it’s something about building an on-ramp for those who care to try to pierce into something.

There's a foolishness in embracing slop-poetry over real poetry. Yeah, you can ask 100 casual Americans who haven’t put any time into reading or understanding poetry, and they’ll all prefer LLM outputs because they have a tendency for explicit clarity, but maybe it’s worth having some opaque mediums. When it comes to essays, I think accessibility is important. But poetry is supposed to be cryptic and mysterious. It’s a feature that it haunts you and reveals itself to you over decades. For every thousand who balk at it, it finds one person to completely infiltrate. I’d be curious to see this same study among poetry readers.

The only personal brands that survive in the age of AI are the ones that are unoptimized.

I discovered today that I could write a journal entry that is intentionally illegible to my future self. I’m writing letters, but blending them so loosely that it would be undecipherable to anybody. This means I can write fast and say whatever I want, and nobody will be able to return to this, which opens up a certain kind of confessional/abstract valve. It’s a way to use “writing as thinking” but encrypted in a way so the shadow can come out.

It’s totally normal to not know what to expect to happen from writing. Writing generates opportunities you can’t expect. My method is to keep adding things to my website, regardless if they make sense in the moment. Retroactively, you can connect the dots. You can use tags to link posts. So if I wanted to suddenly get into a conversation with a VR founder, I could send them a /virtual-reality sub page.

It’s only a % of what’s on my site, but I can slice specific cross-sections through my full range of interests (which is illegible as a whole). Since I have permission to explore anything, I’m pretty generative, but I've found that when I set specific, restrictive rules, I block myself.

Over time (ie: every 6 months to a year) you might gain clarity on if it’s worth converging around a single direction (ie: band reviews vs. teaching music vs. something unrelated).