michael-dean-k/

What and how you read should heavily depend on what your goal is. Outputs shape inputs. When someone insists you go back to read The Great Books, in order, in their entirety, they're giving you bad advice. It's not that those books aren't great—I hope to read Paradise Lost and Dante's Inferno and Finnegan's Wake and the Odyssey before I die— the problem is it's too generic a suggestion. To spend thousands of hours deep in the canon will obviously change you, but that's equivalent of throwing a beginner into the depths of the Atlantic Ocean, hoping they'll figure it out, with no sense of what their goals are.

If your goal is to write essays (every day, week, or month), then you're reading diet should look very different from a philosopher, professor, or researcher. You might not need to be a professional reader, but you should still strive to be a serious one. 3-4 hours a day might not be feasible, but 30-60 minutes per day through an intentionally selected list of sources will slowly build maps of material to fuse into your work.

If you're an essayist, you read so that concepts, forms, feelings, and words are always within reach from an idea of your own. It's no use quoting Aristotle from memory if you can't bend Aristotle to augment an original idea of your own.

It's time to make a syllabus. I've been guilty my whole life of haphazardly reading books and essays as I come across them, but now that I'm over 5 years into writing essays, I feel it's time to be more intentional. This essay is the artifact of me mapping out what, why, and how I'll be reading in the next 2-3 years. I've broken it into four practices: reading for ideas, reading for craft, reading for words, reading for feeling.

Reading for ideas

Since essays are so personal, it's very possible to draw from nothing else than the bank of your own life experience. Memory is absolutely one realm of material, but also, it helps to pull concepts from the world around you, in your time and in all times before. Anyone is exposed to some sliver of culture, and I suppose you could just rely on that. But there's another path which involves actively educating yourself.

Before I dive into the details of philosophy or history, I'm going to build a map. I want to go wide, not deep, because my existing maps are too fuzzy. ie: Who was Thomas Aquinas? Who influenced him, who did he influence, and could I hand write an essay on three of his big ideas? Until I can do that with 100 figures from antiquity to now, all interconnected in a web, I'm not prepared to dive into any Great Book. It would be a tremendous waste of time, for me at this moment in my life, to read The Leviathan by Hobbes in full, especially when I could read 30 pages on it from Alan Ryan, a philosopher-curator, whose prose is 400 years more modern, and who can contextualize old ideas into the full history. In the time I could finish one book from Hobbes, I could read Ryan's entire textbook and know 30 different thinkers at much higher resolution than I know now. By the end, I'll have an updated index on the history of political philosophy, and maybe I'll know that—based on my current writings—it makes more sense to dive into Rousseau in full.

How would my mind be different if I found and read the best curator across every field?

There's a specific kind of book I'm looking for to update my maps. It's not a textbook. It's similar in it's encyclopedic range, except it is slanted by a thesis, animated through a fervent voice, and concerned with the psychology behind the person known for an idea (instead of just biographical facts). Each chapter focuses on a figure for 25-50 pages, which feels like the right level of immersion. It might take 2 hours, compared to 20 hours for the source, and 20 seconds for Claude. While AI can surface historical ideas perfectly suited for your working draft, the problem is you outsourcing your recall. The recommendations are mechanical, impersonal, and worst of all, disembodied: you can't do it in your own head. By reading a sharp longform essay on Aquinas, his ideas will crystallize in my head and load into my subconscious; I'll know when he's relevant to my ideas at the layer of thinking itself.

The nudge to read all of Aquinas from scratch, on principle, is like asking a software developer to derive Internet standards from scratch instead of using libraries and plug-ins. For any thinker that matters, there's at least one person who spent a good deal of their life deeply understanding the source and distilling the concepts for you.

I'm going to share my working list, but the main caveat here is I'm not going in any particular order, and it's not necessary to read cover-to-cover. In any given month I'll be reading 1-2 chapters from 10 of these 24 books. In 45 minutes per day, I can get through most of this by the end of 2028 (2.5 years from now). Everything was published within the last one hundred years, and the whole thing costs $327.

• Literature: Harold Bloom, The Western Canon: The Book and School of the Ages (1994) $11
• Essays: Karshan & Murphy, On Essays (2020) $27
• Architecture: Kenneth Frampton, Modern Architecture: A Critical History (1980) $15
• Arts: Kenneth Clark, Civilization (1969) $3
• Design, Christopher Alexander, A Pattern Language (1971), $34
• Poetry: Nineteenth Century American Poetry (1996) $9
• Politics: Alan Ryan, On Politics (2012) $15
• History: William & Ariel Durant, Lessons of History (1968) $14
• Economics: Richard Heilbroner, Worldly Philosophers (1953)
• Science: Bill Bryson, A Short History of Nearly Everything (2003) $11
• Mathematics: Morris Kline, Mathematics: The Loss of Certainty (1980)
• Technology: Walter Isaacson, The Innovators (2014) $17
• Media: Denis D. Cali, Mapping Media Ecology (2017) $47
• Cosmology: Brian Greene, The Hidden Reality: Parallel Universes and the Deep Laws of the Cosmos (2011) $5
• Philosophy: Bertrand Russell, History of Western Philosophy (1945) $8
• Psychology: Morton Hunt, The Story of Psychology (1993) $12
• Antiquity: Arthur Hugh Clough, Plutarch's Lives (Volumes I and II) (2018) $10
• Religion: Huston Smith, The World's Religions (1958) $12
• Christianity: Fifth Edition, The New Oxford Annotated Bible with Apocrypha (2018) $16
• Orthodoxy: Kalliostes Ware, The Orthodox Way (1979) $10
• Mythology: Mircea Eliade, Patterns of Comparative Religion (1949) $17
• Esoterica: Manly P. Hall, The Secret Teachings of All Ages (1928) $1
• Hermeticism: Franz Bardon, Initiation into Hermetics (1956) $20
• Death: The Oxford Book of Death (1983) PDF

You'll notice that all the links above are Kindle. This is because I want to have my highlights as atomic markdown files. The goal is not to read, but to write! Mapping and reading is just the setup so that I can read through and find highlights that spark original reactions. Montaigne's whole idea was to talk to his library, to be in conversation with the past through his books. And so the goal here is not to finish X books per year, but to produce original material. This is close to sounding like a Zettlekasten, but I should clarify that I don't plan to meticulously arrange my private highlights. A highlight is simply a prompt for an original paragraph that will immediately live on my website.

Other ways to read

I haven't spent as much time mapping out the other three modes, so I'll cover them briefly below, knowing I'll expand them later.

• Reading for craft: If you writing essays, then reading them is how you learn through osmosis. It's where you pick up on the patterns on form and voice, consciously and subconsciously. My thinking here is to pick one essayists per week, read as much I'm inspired to, and move on. It's important to cycle here, because hanging too long on any one writer might lock you into a particular influence without realizing. I'm planning a summer syllabus for Essay Club so we can do this as a group.
• Reading for words: Two years ago, I got really into reference books: dictionaries, usage dictionaries, the thesaurus, etymology, and even specialized dictionaries (on architecture, philosophy, scientific concepts). Sometimes I'd read cover to cover (futile), and others I'd practice words in ANKI. Expanding your vocabulary is seen is a pretentious thing to do today, when so much is geared towards simplicity and accessibility. Won't a rare word alienate the average user in your audience? No, because in the right context, ambitious words can increase the resolution in how you describe something. There's a joy in searching for words, but again, this comes back to returning to them repeatedly until it's actually coming through your prose.
• Reading for feeling: Novels and poetry are less about collecting bits to synthesize into your work. This is more an act of expanding your understanding of how words can make you feel. Less about analysis, more about immersion.

Every generation needs to find its invisible canon to solve its crises:

The last 2 years have been a deep dive into essay composition, but I want to think harder about taste. Of course, I believe fundamentals come first. If you don’t have fluency to express thoughts, then it doesn’t matter what your taste it. Taste without articulation is something like a status trap. People take pride in sitting at the intersection of three particular aesthetics, and using it as a razor to justify their artistic decisions, an excuse to avoid the militaristic discipline required to learn the fundies.

I’m sure there are proper terms for this, but I’m going to riff on taste and derive it all from scratch. Could be fun to read back on this in 10 years.

Yes, anyone can have a taste developed through circumstance, but that’s “narrow taste.” Algorithms make it easier to fall into taste traps. You see the same thing over and over; you are a Substack psychographic; confident in your uniqueness, but you’ve been force fed the same slop as 1.2 million other people.

And then there’s “wide taste,” which is a lifelong practice of reading from odd, competing, singular, idiosyncratic silos. Only by being well-read can you actually build proper maps of a culture. There really isn’t a shortcut to cultivate taste, it takes tremendous time and effort; without it you’ll only be able to cling to feeble, flimsy opinions.

But it’s not enough to read widely; there’s “discerning taste,” the ability to selectively pluck out a small percent of the things you’ve read and deem them as special. 

Ultimately there are questions on what to read, and well-read people tend to point to old books, the canon, but that feels like outsourcing your discernment. What good is the canon? Sure, if it's survived for centuries, there's probably something to it, but it risks turning you into a homogenized intellectual if that's your only source (and yet also, it helps to know the classics so you can speak that language, but it's probably best to supplement with 50% nn-canonical sources).

The question behind the question is this: what is the point of a serious reading habit? I’d argue that you read to understand the range of ways that words can move you, and to accumulate ideas and lenses that help you navigate the circumstance of your life and generation. The western canon might have some overlap, but not all Great Books are the books you need. The western canon is helpful as a history of literature, a record of how the species bursted through with original linguistic concepts and forms. That matters! That’s worth studying if you want to understand your heritage, your species, the norms of older times, and the outer limits of language.

But from a perspective of “renaissance” or “revival,” to surface old ideas to help our current situation, that’s a very different canon. So the word “canon” is flexible. You hear people making “personal canons” all the time now, which are effectively, just the books you like. There are also "tech cannons" and even the "China tech cannon." But you could argue that as society mutates, each generation has their own invisible canon, some combination of obscure books, that if discovered could help them navigate the narrow passage oftheir time.

Can AI have taste in this kind of canon creation? Maybe a culture progressively rots if each generation is unable to find the scattered canon that’s destined to them, and maybe AI can help reverse our fumblings. The question then is, what do humans lose? What matters in the act of canon creation? The orientation (the thesis on what’s worth finding), the mapping (selecting the books), the reading (digesting old books), or the synthesis (making new things from old readings)?

I asked as AI about what we lose, and here's what it said, which I don't buy:

But Taste—true, earned taste—is a byproduct of the inefficiency of finding those things yourself. When you hunt for the “Generational Canon” manually, you have to wade through trash. You have to read ten books that don’t resonate to find the one that vibrates in your hand. That wasted time isn’t waste; it’s calibration. It provides the contrast necessary for “discerning taste.” If an AI hands you a perfect platter of 10/10 bangers that align perfectly with your soul, you lose the ability to detect why they are good. You become a connoisseur who has never tasted a bad wine, which is to say, you aren’t a connoisseur at all; you’re just a consumer of high-quality inputs.

I think there is enough discernment and active reading within a book that helps with calibration. ie: I'd rather read through the right recommended book 5 teams, then wastefully read 4 books that were trash, so that I can find the right book and read it once. My gut says that the beginning and end of the workflows are most important: orientation and synthesis. The mapping work is for specialized canon makers, which could be humans or agents. Even when AI provides you a map, there's still research to do on each book, and discernment on where to plunge.

The reading part is more nuanced. Of course, when you don't read, you can't synthesize. But maybe AI can assist us finding the right things in a given book. As in, maybe Infinite Jest is just so thick that I'm going to procrastinate on starting for a decade. But maybe there's a 50-page excerpt in the middle that is hyper-relevant to the month I'm open to having AI summarize the beginning and end, so that I can dive in and experience the right passage at the right time. This doesn't replace reading the full thing, and maybe that will happen in a future stage of my life. This feels like a middle ground—I'm not saying I want to extract summaries and factoids for other purposes; I do want to immerse in the text for 10-20 hours, I just don't have 100-200 hours in that given month, and so in this case AI is doing what a college professor does: curate.

12:41 PM – On self-taught writers and the crucible of an audience:

Once I have my anthology scored, I can compare it with Best American Essays (2024/2025), at least in terms of “composition quality.” I definitely think it’s possible (we only have to get higher than a 3.7). 

The mystery to me is, how is this possible? How is it possible that a bunch of self-taught writers can put together better essays than people with English degrees, MFAs, and status badges from being featured in notable magazines?

I have a guess: the independent writers who operate in the free market of readers has more incentive to improve. They publish, get instant feedback, and publish again, either a week or month later. They have total autonomy to evolve their topics, their forms, their voice. They need to put in the work to make something great (it’s not enough to get a commission, and to make it good enough to live in the magazines). What the independent writer has is more feedback, more speed, more freedom, more stakes. 

Compare this to the writers who swarm the literary institutions: they often get no feedback, publish maybe only a few times per year, have to conform to the house style, and the magazines carries all the stakes. There is a staleness that comes from being disconneted from your readers.

So even if literary writers have something like a 5 -year head start, self-taught online writers have a higher slope, and can far surpass the average MFA graduate in terms of ability. (And this is without any kind of formal independent writing education! This is a good reminder/anecdote for me to remember in terms of my curriculum/texthbook/app).

The difference between professional writers and independent writers (I think), is that independent writers are more immersed in a life that is less writing-oriented. A professional novelist is writing full-time, but important essays are often written by people doing other things full-time (raising a child, building a company, working in an industry, etc.). Essay anthologies could be so powerful because they aggregate the well-articulated thoughts of normal people—who make their specialized problems universal—into a powerful literary medium that can be digested by the public. A good annual anthology, then, gives the culture a tight feedback loop where they can make sense of a complexifying culture. And given how the essay is about “questioning” and running down alternate modes of thinking; the mainstreaming of the essay is mainstreaming alternate modes of thinking and living. (This is very Adorno in spirit.)