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On Monday 6/15, I'm hosting a workshop to kick off a reading group for classic essays: RSVP here.

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Michael Dean
michael-dean-k/

Architect-turned-writer, founder of Essay Architecture. Building pattern languages, software, anthologies, and community for essayists.

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Michael Dean
michael-dean-k/

Architect-turned-writer, founder of Essay Architecture. Building pattern languages, software, anthologies, and community for essayists.

Essay Club ↗
Michael Dean
Michael Dean

Architect-turned-writer, founder of Essay Architecture. Building pattern languages, software, anthologies, and community for essayists.

Michael Dean
Michael Dean

Architect-turned-writer, founder of Essay Architecture. Building pattern languages, software, anthologies, and community for essayists.

Essay Club ↗
Michael Dean
Michael Dean

Architect-turned-writer, founder of Essay Architecture. Building pattern languages, software, anthologies, and community for essayists.

Entering the bible

· 924 words

A goal of mine has to read the majority of the Bible—New and Old Testaments—by next Easter, which means I need to start soon, next month, September, and carve out 15 hours per month or so. My original plan was too simple. I decided on the The Oxford Annotated 5th edition, but that has limitations. It's academic and “non-confessional,” meaning, it’s not any particular church’s perspective; it’s the best in terms of secular scholarship, and is the standard in Ivy league religious departments. It’s probably great for the historical perspective, but it doesn’t include the other perspectives at all.

I do want to contemplate the allegorical, typological, and moral angles of the Bible too, but my decision is whether I want (1) a single perspective (the Orthodox perspective), (2) no perspective (so I’m forced to derive my own), or (3) a range of perspectives (which I would have to critically triangulate). Each approach would offer something different. I already have Kallistos Ware on my reading list—on theology, on the church, on the Philokalia: focused on Orthodox prayer—but all that doesn't include the Orthodox angle on the Bible.

I'm not necessarily looking for a traditional Orthodox outlook, but rather an Orthodox foundation for a personal and idiosyncratic outlook. I think creative liberty in interpretation is how to best engage with a religious text.

This ties into an idea I have about seeing religion through the three lenses of philosophy: ethics, metaphysics, and epistemology. I find myself agreeing with the ethics and metaphysics of Orthodoxy (how to live, and the nature of reality), but disagreeing with the epistemology of religion in general; epistemology is about how we attain knowledge, and most religions are anchored in fixed answers to life’s biggest mysteries. (...Yes, even within a sealed worldview, there is still work to do in building a personal relationship with the material, but this does not include doubting the core dogmas...). My view is that the deepest form of spiritual practice comes from tolerating ambiguity and directly grappling with the mysteries; this involves questioning central axioms, inventing original interpretations, and extending scripture forward.

Here's the latest game plan on how to achieve this—it involves five different Bibles:

  • I found three specialized translations (one for the Old Testament, one for the Gospels, another for Acts/Letters/Revelations) that are most faithful to the original linguistic intent. They’re translated by philologists/classicists/philosophers. After reading samples from a bunch, I found these to be the most literary and engaging to read. I’ll read these without commentary, and take notes with my own interpretations.

  • After reading a book (ie: Genesis), I’ll read the The New Oxford Annotated Bible (Fifth Edition), but only for the historical introduction for that book (ie: Genesis has about 10 pages, where the Orthodox Study Bible only has 2). The Oxford commentary felt a little too unstructured and pedantic, though I imagine for some books, I will dive in.

  • Before moving onto the next book, I’ll read the commentary from The Orthodox Study Bible. In addition to line-by-line commentary, it also has short essays which I found great for synthesizing everything. This gives the frame for my church and the specific religious tradition I grew up in.

The value in this process is: (1) I start with the source text, without commentary, meaning I get to record my own idiosyncratic first impressions; but then, really, (2) I compare those impressions with a range of sources that don't agree. This ties to some good general reading advice I recently heard: simultaneously read books on a topic that have diverging conclusions. There's a tension when three different books interpret Genesis differently. Is the snake the devil? By levitating above any singular perspective, but taking all sides seriously, I can build a better understanding of the hyper-object (rather than a fixed perspective).

The syllabus: (NT = New Testament; OT = Old Testament; DSS = Dead Sea Scrolls)

  • August 2026: (430 pages)
    • The Gospel of Mark (NT)—145 pages
    • Psalms, Book I (OT)—155 pages
    • The Book of Isaiah, Ch. 40-55 (OT)—130 pages
  • September 2026: (500 pages)
    • Genesis (OT)—425 pages
    • Psalms, Book IV (OT)—75 pages
  • October 2026: (440 pages)
    • Exodus (OT)—365 pages
    • Psalms, Book II (OT)—130 pages
  • November 2026: (525 pages)
    • Samuel 1-2 (OT)—445 pages
    • Ecclesiastes (OT)—80 pages
  • December 2026: (480 pages)
    • Letters of Paul, T,G,C2,R,Pp,Pm (NT)—330 pages
    • Damascus Document (DSS)—25 pages
    • Habakkuk (OT) + Habakkuk Pesher (DSS)—40 pages
    • Psalms, Book III (OT)—85 pages
  • January 2027: (550 pages)
    • The Gospel of Matthew (NT)—225 pages
    • Deuteronomy, Ch. 1-11, 27-34 (OT)—120 pages
    • The Book of Jeremiah, Ch 1, 7, 11, 28-44 (OT)—160 pages
    • The Minor Prophets, Micah—45 pages
  • February 2027: (525 pages)
    • The Gospel of Luke (NT)—240 pages
    • Acts (NT)—225 pages
    • Minor Prophets, Jonah (OT)—15 pages
    • Minor Prophets, Joel (OT)—30 pages
    • The Community Rule (DSS)—15 pages
  • March 2027: (425 pages)
    • The Gospel of John (NT)—185 pages
    • The Gospel of Thomas (DSS)—30 pages
    • Proverbs (OT)—210 pages
  • April 2027: (495 pages)
    • The Book of Ezekiel, Ch 1-3, 8-11, 18, 33-39, 43, 47 (OT)—130 pages
    • Minor Prophets, Zechariah (OT)—80 pages
    • The War Scroll (DSS)—20 pages
    • Psalms, Book V (OT)—140 pages
    • The Revelation of John (NT)—125 pages

Reading Malfunctions

· 338 words

Given I’m slightly sleep deprived these days—less so from a baby that wakes up too often (she often sleeps through the night); more so from waking up very early to get in a work shift before my wife leaves for work—I often fall asleep reading.

Mortimer Adler said if you fall asleep reading, you should stop. If you’re drowsy, you aren’t sharp enough to read analytically. He’s probably right. I notice a gradient in how active I am with my reading: sometimes I’m punching mini-essays into my Kindle for each highlight; other times I highlight and move on.

Nonetheless, I have noticed some interesting recurring phenomenon as I fall asleep reading, which I’ll call “reading malfunctions.”

The first malfunction is when, as I drift off, I notice the text on the page get slightly blurry, and find myself reading text that actually isn’t there. It’s like a hypnopompic literary hallucination. I’ll read a string of words, wake up, and then look for that string of words to continue, but it’s nowhere in the paragraph, nowhere on the page. It must be something like the subconscious filling in detail to the larger gestalt of the page.

The second malfunction is when my eyes actually close, yet there’s still the inertia of gliding across strings of prose, but at this point I’m seeing an image or idea instead of text, and I’ll notice that it’s often not even directly related to the text, just some association that I can’ quite connect.

The third malfunction, and maybe my favorite, is when I doze off and process only the geometry of the spaces between the text. I stop seeing letters or words, but the void between words, and the patterns that happen to occur from that particular combination of words. Sometimes they look like clouds, or mountains, or aztec symbols; it’s the similar pareidolia effect from cloud gazing. (I imagine AI might get to a point where it can simultaneously compose “void art” that matches the meaning of a paragraph).

Canonical centers

Which five books are at the center of western civilization?

· 263 words

After reading The Odyssey, I now appreciate how the Faust story is an Odyssean story. I realize there’s a whole range of books that will resnoate more now that I have more context into Homer (ie: I’m inspired to read Dante's Divine Comedy, knowing Odysseus is in it). The Odyssey unlocked Joyce’s Ulysses, Virgil’s Aenid, Gulliver’s Travels, O Brother Where Art Thou?, as well as books that are extensions and reimaginings of Homer’s World—like Atwood’s The Pennelopiad, and Kazantazkis’ sequel.

It got me asking: what are the 5 cornerstone works of western civilization? Which five books, if read, would give you the context to appreciate almost any other book? I came up with The Odyssey (narrative), Plato (reason), The Bible (morality), Shakespeare (psychology), Montaigne (inquiry?).

I share the category in parenthesis to note that each one has to live within a distinct sphere (ie: you can't have Plato and Aristotle, nor can you have Lord of the Rings, because the Odyssey has the narrative/mythic/epic slot). Also, a work should have a minimum of 500 years of influence.

Montaigne may be a stretch (related mini-essay on this here), but it does seems like the entire form of essays points back to him.

Worth noting other picks I considered: Arthurian legend, One Thousand and One Nights, Frankenstein, Sherlock Holmes, A Christmas Carol, Alice in Wonderland, Moby Dick, Dracula, Lord of the Rings, something by Kafka, One Thousand Years of Solitude, Harry Potter, Augustine’s Confessions, Paradise Lost, Infinite Jest, Faust, The Divine Comedy, Hesiod’s Theogony, and Ovid’s Metamorphosis.

I have become a creature of reading

· 450 words

After being a father for six months, here’s a predictable observation: days feel similar. I bring my daughter out, of course, to parks and pools, so we’re not entirely homebound. But I can’t, for example, spontaneously take a train to Manhattan the night of July 3rd to see the ball drop before the semiquincentennial—it’s not that I particularly want to do that, it’s just that every impulse to “get out” is filtered through, an is-it-worth-doing-this-with-a-stroller-and-supplies filter, or an is-this-even-possible filter, or a would-this-be-inconvenient-to-my-wife filter. There is a common groove: work bright and early, baby stuff all day, and then resetting, relaxing, and recalibrating at night.

So, at least for now, there is notable change in “experience.” Not a change in quality, but in type; it’s a lapse in variety of experience, which personally doesn’t bother me. Your mental fortitude for early parenting probably bears some resemblance to how you fared during the pandemic. There is no virus, but a similar warping in the nature of days.

But, the pearl and point of having kids is the experience of raising a child; it lacks the variety that a single nomad in Bali might have, but it is a singular channel of experience with extreme depth, meaning, and change. Once you figure out how to make your kid laugh, and how to intuitively communicate without language, and where they are ticklish, and how to guide their attention to get them to focus on books—you discover the tremendous variety within the thing that matters most.

As a writer though, it seems like I prevent myself from writing about parenting. I tend to mention it loosely, without my daughter’s name and without much detail. I always find myself not thinking linguistically in moments with my kid. Maybe I should? I just usually forget. There feels like so much nuance packed in a single event and glance, that to stop and write it both severs me from the potency of it, and sever me from them.

So, while I find myself in recent months with few “stories” I’d happily share an essay around, I do find myself reading more than I ever have in my life. Considering she sleeps a lot, on me, it’s just a space I have. I imagine when she starts walking, or gets older, this might evaporate, but for now I’m reading 1,000+ pages per month. I feel less anxious about the lapse of new experiences, knowing that in a few years it all comes back, and I’ll come back with a new head, a new constellation of nodes to bring to the variety of experiences, along with a little person who will force me to see everything anew.

1% Compression

· 282 words

A summary is maybe 1% of the original, but notably it loses all of the source—this is what defines the flat blurb, the just-in-time factoid. A functional interpretation.

A compression is different in that it can only draw from the source. I’m finding that 40-70% compressions reduce length but increase information density.

What would a 1% compression look like? In a 10,000 word essay, which 100 words might contain the smallest fractal of the whole, both in terms of substance and style? This doesn’t amount to selecting your favorite paragraph, but finding your favorite 5-10 sentences from across a piece, and stitching them together, so that the kernel of the idea, the thing that’s likely to remain after the brutal compression of memory, is right there in front of you.

For every essay I read, what if I required myself to make that 1% compression? What if I returned to that list often, quickly refreshing the way a piece moved me. Would I actually remember them over time? Would I actually enact those lessons and change my life?

I wonder if there’s both an expansion and compression arc that’s required to fully get something: XS>S>M>L>XL>L>M>S>XS. You start small to even build intrigue to enter a text (ie: a recommendation from a friend); maybe you read smaller compressions, and gradually build up to the XL full version, with all the footnotes, annotations, and liner notes. But then there’s an equally necessary process of unwinding, of distilling and compressing what you uniquely take away from something—perhaps an aphorism; a souvenir on your shelf that is lodging into your working memory each morning.

My personal reading syllabus

· 5,873 words

Here are three maxims that shaped why and how I built the syllabus below:

  • You become your syllabus. An essay writer should read differently from a general reader. Every inspiring quote becomes a seed that could launch an essay, or at least be woven into one. This syllabus is an attempt to shape the books that I want to shape me. I've organized the book into four genres (and each has subdomains): I read Essays to understand the form, since that's the same form I'm creating with; I read History so that a literary curator can help me build maps of people and concepts across different disciplines; I read Non-Fiction to go deep on the ideas I want to write more essays on; and I read Fiction to understand the different emotions and moods that words can render (also, fiction teaches allegory, which is about embedding concepts into tangible symbols; I imagine DFW is the essay writer he is because he was primarily a fiction writer.)

  • Converse with the authors. A Montaigne essay is often filled with dozens of quotes. His essays likely originate from his commonplace book, his collected quotes from Seneca, Plutarch, Epicurius, Augustine, etc. I've been reading on Kindle for two reasons: (1) because when my daughter is sleeping on me, it's much easier to read one-handed; (2) all my highlights get synced form Kindle to Readwise to my own app. This makes it easy to resurface highlights and write short, original essays in response to them. They're all gathered on my website. This helps enforce the idea that it's not about having read the book, but about using the book as a way to inspire original writing. And of course, by writing about and in response to books, I remember them much better.

  • Non-linear reading. Since the end goal is to read to produce writing, I don't necessarily need to finish all 121 books here or go in any particular order. For many of the books in Histories, I'm reading a chapter per month over 2 years. For some works in Non-Fiction, I've done an inspectional read and have selected just a handful of chapters that I think are most relevant to me. Generally, there are many textbooks running in parallel, and then each month includes one work each from Essays, Non-Fiction, and Fiction. I built a "syllabuilder app" to plot out what was possible to read in a given month (which is why I track page numbers below). This month I have 19 books I'm reading simultaneously. In any given day I might jump around 3-4 books. Overall it's less than 1,200 pages per month, or 40 per day, which matches a graduate level syllabus (probably 60-90 minutes per day of reading). I'd say this is like a reading list for a Master of Liberal Arts with a focus on the essay, moral philosophy, and civilizational thinking. This is roughly 6 semesters worth of reading, so it can be done in 2-3 years. The goal is to "finish" this by the 2028 election (acknowledging that I have permission to stop any book if it's not fruitful).


I. ESSAYS

1a) Essay Books

1b) Anthologies & Criticism

II. HISTORIES

2a) Humanities

2b) Civics

2c) Spirit

III. NON-FICTION

3a) Virtues and Ethics

3b) Psyche and Attention

3c) Craft and Education

3d) Politics & Economics

3e) Technology and AI

IV) FICTION

4a) Modern Fiction

4b) Classic Fiction

4c) Science Fiction

Footnotes

  1. (3 units: Nature=115p, Vol I=170p, Vol II=150p)

  2. (selected 230p)

  3. (5U I=15p; 1580=35p; 1900=56p; '60=53p; '90=60p; 219p)

  4. (In+F,Ad/Lm/Hz,Bk/Brg,Th/Bl/L=4u56p/m, 224p)

  5. Books I–III (eudaimonia/virtue), Book VI (phronesis, practical wisdom), Books VIII–IX (friendship), and Book X (contemplation), 2019 (140p)

  6. Ch 1-5,9,14-18, 1981 (176p)

  7. (1-5,15-22 = 225p)

  8. (The Hedgehog and the Fox, Two Concepts of Liberty, Historical Inevitability, The Counter-Enlightenment)

  9. (1851-1854 = ~115p )

  10. (2,4,5,6,11,12=235p)

  11. (406p, so break into 2 unit cards for 203 words each, Parts I-II and Parts III-IV)

  12. (Ch 1,2,4,6,9,11,14,16,18 = 221 pages

  13. (245p)

  14. (I, parts of III-V, VI-VIII = 274p)

  15. (first half = 248p))

  16. (excerpts at 200p)

  17. (excerpts at 150p

  18. ("The Dead", "Araby" "The Sisters" "A Painful Case" "Eveline" "Counterparts" "A Little Cloud" "Clay") " (111p)

  19. (Hills Like White Elephants, A Clean Well-Lighted Place, The Snows of Kilimanjaro, Indian Camp, Big Two-Hearted River, Old Man at the Bridge, A Day's Wait, Now I Lay Me, The Gambler the Nun and the Radio, Cross-Country Snow (104p)

  20. (The Jilting of Granny Weatherall, Flowering Judas, Theft, Noon Wine, Pale Horse Pale Rider = 135p)

  21. (The Bear Came Over the Mountain, Family Furnishings, = 68pp)

  22. Break It Down, Story, The Thirteenth Woman, Kafka Cooks Dinner, Varieties of Disturbance, We Miss You & selected shorts = 80p

  23. (The Death of Ivan Illyich, Father Sergius, Alyosha the Pot, Hadji Murat = 232

  24. (Notes from the Underground, The Peasant Marey, A Gentle Creature, The Dream of a Ridiculous Man = 176p)

  25. (A Boring Story, The Darling, The Man in a Case, Gooseberries = 86p)

  26. Harrison Bergeron, Welcome to the Monkey House, Long Walk to Forever, Miss Temptation, All the Kings Horses, Tom Edison's Shaggy Dog, New Dictionary, More Stately Mansions, Report on the Barnhouse Effect, The Euphio Question, Unready to Wear, The Kid Nobody Could Handle, EPICAC, Tomorrow and Tomorrow and Tomorrow = 168p)

  27. (The Library of Babel, Funes the Memorious, The Garden of Forking Paths, The Imortal, Death and the Compass = 64p)

  28. Bloodchild, Speech Sounds, The Evening and the Morning and the Night, Amnesty = 115p)

  29. (Story of Your Life, Understand, Hell Is the Absence of God = 100p)

  30. The Ones Who Walk Away from Omelas, The Wife's Story, Buffalo Gals Won't You Come Out Tonight, Nine Lives, Vaster Than Empires and More Slow = 150p

  31. (Alphinland, Revenant, Dark Lady, The Dead Hand Loves You = 130p)

The voids between letters

· 65 words

I was falling asleep while reading one of Henrik's essays (not because I was bored, but because it was almost midnight), and something weird happened. As I dozed off, I noticed that I stopped processing words and even letters; instead I only registered the black space in-between white words. It was something like prose-paradeolia. I could see accidental faces or objects in each paragraph, composed solely out of spaces. I imagine we’re not far from an AI that can generate paragraphs that have corresponding “shadow art.”

Researching the Essay

· 203 words

I’ve embodied the role of researcher these last 3 days. I fear a disorderly private spiral, yet also, I might be more obsessed with Essay Architecture than I’ve ever been.

If I want to write about “the essay,” I feel like I couldn’t do so in good conscience without reading the top books on criticism (On Essays, Essayists on the Essays), the top guide books (Elements of Style, On Writing Well), a curation of literary forms, and maybe even the introductory essays to The Best American Essays series since 1986. Throw in a few hundred essays too. This isn’t so unreasonable. And it’s definitively not “avoidance,” as long as I write through the whole process.

What definitely has to change though is the nature of publishing. At the year’s start, I set a plan to carve through pattern-by-pattern: 1.1 > 1.2, >1.3 > 2.1. Now, I’m more so like a gas filling all the crevices of the hyper object, collecting specimens, and slotting them into a map. I should probably just be hyper-publishing everything I find, every highlight, without much thought or strategy. If my process is chaotic, my publishing should be chaotic. And yet, at the end, the order will present itself.

Corpus Shock

· 28 words

A word for the shock of unexpectedly finding a whole tome of work from someone you know that is larger than you can digest in a single sitting.