michael-dean-k/

250 years ago lived an arbitrary man who I can call my ancestor. He was one of 256 of my great great great great great great grandparents. It is unlikely that any of them ever met, but there was very possibly a moment where two strangers crossed in a street, or shared a boat unknowingly, or exchanged pleasantries in insignificant and instantly forgettable ways, not knowing their great great grandchildren would give birth to my great great grandparents. My existence depended on the whims of those 256 people—their triumphs and disappointments, decision and indecision, love and otherwise. Compelled by nature or eros or God to breed with a specific person at a specific time, they continued casting down the great chain of being.

How alike am I to any one of them? If my parents can each claim 50% of my traits, then my great^6 grandparents each only claim 0.39%.

In one sense, I bear almost no resemblance to any of them. Maybe, in an Empedoclean sense, you might see my nose roaming around a town square, or my hairy feet wading through a field. Any one ancestor might feel no affinity towards me; if I knocked on their door after accidental time travel and needed a place to stay, they might just past off the responsibility to one of my other 255 ancestors. Over enough centuries, your descendants balloon past a scale you can adequately care for. My wife, for example, is part of an old royal Welsh family that goes back to the 1250s. She even has a family ring. Yet, by the theoretical logic above, she is one of millions with a claim to the throne.

In another sense, a more romantic sense, my 256 great^6 grandparents represent a still very small sliver of the human population. 0.000000256%. If any of them had any resemblances to me, physical or mental, I’d like to know. Of course, our consciousnesses would be quite different, for identity is forged from circumstance, but I don’t doubt that I would find uncanny resemblances. When I hear the lore of my great^2 grandparent, a peasant on a dry, rustic, Greek Island, and how he was able to harvest and sell rain water to get rich, I wonder if his entrepreneurship speaks to my own entrepreneurship. It is quite vague to trace influence back even 1-2 generations, let alone 8 or more, but nonetheless, the actions of those people did eventually lead to me, and there are all sorts of ways their myths and interiors might shed context into my own circumstance, at least symbolically.

Unfortunately though, none of my 256 were writers. At least, not that I know of. Some may have written journals, or written for administrative reasons, but as far as I know, none left a body of work that was meant to be cast and continued through time. One grandfather did have three chapters of an abandoned novel on a 1980s hard drive that my father was able to recover. My other grandfather is uneducated, barely literate, and only writes English in capital letters. Now that I think of it, it’s probable that +95% of my great^6 grandparents could not read or write. Mass literacy wasn’t realized until the early 20th century.

Even though we shifted from oral to written history in Ancient Greece, most family history today is only passed down through spoken stories. They’re etched into memory and unreliably translated down the chain. I can barely trust the stories I pull from my head, planted decades ago, either misdelivered or misremembered. Was she really a psychic midwife that predicted winning horse numbers in her dreams making her son rich until a black hand cut her off? Did he really drive Nixon in a cab?

It would be strange for a society to sleepwalk forward, with no sense of what truly happened before the 1900s. How is that not strange for any of us individually? What if I become the family’s Plutarch? How might a child’s identity differ if they had detailed accounts of their relatives, generations up the chain? I suppose you could ask the great^6 grandchildren of writers. Claude tells me there are 700 members of the Monticello Association, each a genetically-confirmed descendant of Thomas Jefferson, who wrote 19,000 letters, books, and a Bible. A few of them have problems with him being a slaveowner, with one publishing an essay called “Take Down His Memorial.” At least they have 255 other ancestors to respect.

In October of 2024 I sliced history into eras of my own. Prior to that, my historical timeline was built on sandy approximates. The challenge here is that so many historical eras have different time periods (10, 50, 250 years), and so it requires you to remember specific date ranges for specific things. Unless you’re a historian, you most definitely won’t.

I’ve been long drawn to the Strauss-Howe generational theory, and decided to use this as a historical map of even intervals. They break history into “saeculas,” 80-year cycles, the interval of an average human life, and perhaps not coincidentally, the interval between major world conflicts. They go back to the 1370s, I think, but I’m trying to work through the major milestones in the 400 years before that (which includes the Schism, the Crusades, the founding of Oxford, the Magna Cart, Thomas Aquinas, which all seem relevant to the millennia and the rise from the Dark Ages).

The point of a historical timelines of equal intervals is that (1) it’s easy to remember—and I’ve even given my own names to make them stick—so that (2) any new information, ie: ideas or people, can easily slot into that model. It helps to know the Renaissance Era is 1370, Discovery Era 1487, Scientific Era 1594, and Enlightenment Era 1704, so that when I come across Hobbes in 1600s, I know, oh, that’s the Scientific Era, which makes sense because Hobbes brought the first scientific understanding of political philosophy. Today I made some progress on updating my October 2024 map, which I started in 1095 (the Shism) and wrongly named “the scholastic era” (which is better for the following phase).

Instead I think the start should be in 962, and called “The Schism Era.” The new order (I) kicks off with Otto I becoming emperor through the Pope, which is significant because in the prior 75 years, there was no emperor due to the peak of viking/barbarian raids, and it was the biggest threat of Christianity being erased. Since Otto, the Holy Roman Empire stuck for 8 centuries, until dissolved by Napolean, so this really is a reconsolidation, the exit from the Dark Ages. The awakening (II) is a spiritual crisis, when Rome adds the “filioque” a term that alters the original trinity, this leads to (III) the Schism between Orthodox and Catholic church, and erupts in (IV) a civil war between the Church (the Pope) and the (Holy Roman) Empire at Canossa in 1077.

Then the “Cathedral Era” kicks off in 1095 with the Crusades, which is it’s own new world order, where a French faction of Catholicism (pope-aligned), helps launch (1) a cross-country military coalition that supports the church, which can (2) take back Jerusalem from turks, (3) prevent anti-pope revolutions, and (4) thrwart internal civil wars of feuding knights. This leads to Worms in 1112 (II), which is really the original separation of church and state (though really it’s like 2 separate governments, where the church still has laws and the right to kill). This period is marked by many crusades, the rise of cathedrals from this new order (church having a better military with more resources)—Saint-Denis, Cartres, Notre Dame, Cantebury. There are also “cathedrals of thought” maybe a stretch, but includes Aquinas’s unification of Aristotle and Christianity, along with proto-scholars that would lead to Oxford. Where in the last Era, Christianity had barely survived from Magyar raids, this Era is continent-wide flourishing of building, writing, thinking (and of course, conquering). The awakening (II) featured new religious ideas (Gothic, cults, scholasticism, classicism, exuberance), and the overall exubernace spiraled into crises of King John (IV). He taxed heavily to fund failed crusades, seized lands, and jailed nobles, so this resolved with the Magna Carta (1215), which bounds the king to laws.

Following is the Scholastic Era (1215 on), which coincides with Oxford officially incorporating at a university, but I can’t do that one now… I have to leave in 20 minutes to make it to my father-in-laws memorial on time. The point is, from this morning I now understand two historical cycles that were extremely fuzzy to me. Of course there is a lot more to learn, but I have a map that other things can lock into. Most relevantly, I have a sense of the different inner-saeculuar moves ()from I>II>III>IV), which help imagine possible scenarios for today (2026 is the predicted beginning of I, a new world order).

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.