michael-dean-k/

Hey [ * ],

Don’t apologize for rambling; a good part of essay writing is just following a train of thought to see where it leads (and editing after). I enjoy your letters. You can articulate things well, and shouldn’t feel insecure about your words, or feel like you need to use AI.

I think your problem might be the need for certainty before you start. It sounds like you want to know your topic in advance (*), frameworks on how to make an essay, and the standards on what makes it great. These are all important, but I think you’re clinging to them pre-maturely; I don’t think you need to worry about topic, process, or quality until you’ve published 50-100 things. To start, it’s more about establishing the routine of becoming a writer, and once that is flowing, and once it’s almost guaranteed that you will publish something at your ideal interval, then you can start tinkering with other variables, testing if you can incorporate some new goal without interrupting the momentum.

I went through a very similar thing. I took a writing course, Write of Passage, published 2-3 essays, but then stalled. After it was over, I showed up for 100 days straight to my small writing group, and even though I thought, wrote, and edited every day for 1-2 hours, I didn’t publish anything. The core realization is that the process was getting in the way, and I was held back by my own standards prematurely. It’s all about publishing. Thinking and editing don’t count unless you bring a thought to a point where you’re willing to share it. Starting January 2021, I published 1 idea every single day for 45 days, and from there I’ve been publishing semi-regularly for 5.5 years (and through that time, the process continually evolves, and the quality bar varies but generally averages upwards). I’m almost at a million words now. All my thoughts from 2020 and before are mysterious and fuzzy, because I never froze them, and so I can’t know exactly what I thought back then. My most important thoughts since are all legible, and even if they’re poorly written and wrong, I’m happy I have them, for they’re a record of my own evolution.

My advice to you is to start a simple website where you can publish your thoughts every day. Daily publishing is a strong way to break out of a rut. It’s surprisingly doable, and forces you to get out of your head. You should have no expectation for it to be good, no sense of process (imagine writing a stream of consciousness letter like you did to me, but every day, on different topics), and no commitment to a topic (no more than 25-50% on X or Y). These don’t have to be good. Most of them won’t be. But by having them in public, you’ll care about them more, you’ll re-read them, maybe retroactively edit them; but of your first 30, you might have 3 that you’re really proud of, which is 3x more than if you tried to make 1 perfect piece per month.

I don’t think Substack is a conducive place to start this project, personally. If you publish 30 times and get 0-2 likes on each, it will feel like a failed project; if you do that same thing on your own website, it will feel like a massive success. If you don’t have an idea of where you would host your writing, let me know and I can offer suggestions. I’ve created my own site recently with Obsidian/Claude/Github/Netlify, but to start it’s not worth getting hung up on infrastructure. Spend no more than 15 minutes on your setup. There are plenty of minimal blogging platforms that will let you get started.

Let me know if you’re up to experiment with hyper-publishing. It’s about publishing every day, regardless of length (could be 40 words or 400 words).

Note to David on podcast scope:

"Then we can bridge this into writing by comparing 'Consider the Lobster' & 'Shooting an Elephant' (a popular essay by Orwell). In many ways they’re opposite (saving vs. shooting an animal, digressions vs. plot, maximalist vs. minimalist), yet they both score 9/10. Each has a high-concept title (like “snakes on a plane”) which makes the context load light. I’m thinking the majority of X-ray examples can come from these two essays. And since “essay” is part of the framing for my project, it makes sense to deconstruct a DFW essay in high detail (probably the most famous essay since 2000)."

I've been reading through modern writing classics, and I realize that essays aren’t a great way to teach essay writing. Take the book Draft No. 4 by John McPhee. I sense that, naturally, writers care more about their writing than teaching. These craft essays take on the form of short memoirs with beautiful literary voice, but the theory is vague, peppered in, without nuance, and dislocated from related concepts.

I asked AI to read 4 years of posts from the Write of Passage Circle community and make some inferences about me. “Please make elaborate and nuanced observations about the writer in this writing community. This includes most of their posts over 4 years:”

[Thought about writing journey and evolution for 4 seconds]

Then I asked it to review and summarize all of my feedback:

“This person’s feedback style is comprehensive, encouraging, and highly attuned to the writer’s goals and potential blind spots. They typically begin by reading a piece in full, noting both the high-level structure and the sentence-level details, then they leave a warm yet direct set of in-line comments and an overarching summary at the end. On a technical level, they pay attention to flow (pointing out where transitions feel jarring), the rhythm and length of sentences (citing tools like Hemingway to reduce complexity), and the integrity of the introduction and conclusion (urging the writer to hook the reader early and tie loose threads later). They have a particular knack for spotting an essay’s “shiny dime”—the focal insight or big question—and suggesting ways to make that thread more explicit. More personally, they encourage writers to dig deeper into their experiences and vulnerabilities, often recommending they add or expand on anecdotes that bring a concept to life. Emotionally, they aim to both reassure and push the writer; they highlight what’s working well so the author feels confident, while showing them how certain passages might confuse or overwhelm readers. On a psychological level, they aren’t afraid to address hesitations or anxieties about publishing, reminding people that the aim is personal expression and growth, not robotic perfection. Their feedback also has a subtle empathetic dimension: even as they recommend major cuts, restructuring paragraphs, or clarifying language, they do so by linking those decisions back to the writer’s intent, audience expectations, and the unique voice that should shine through. They encourage the writer to remain playful, observant, and personal (the POP framework), and to see revision less as “fixing mistakes” and more as a creative opportunity to clarify the core idea. Across their many comments—whether they’re dissecting a tricky hook, advising a friendlier tone, or praising a bold personal story—they balance methodical critique with genuine enthusiasm, prompting writers to embrace edits as part of discovering the essay’s essence and pushing it to the next level.”

(Note for an essay contest with LWS:)

Whatever genre you write in, if it’s made of prose, it’s made of paragraphs. E.B. White said the paragraph is “the unit of composition.” The idea that each paragraph contains a unique thought is an ancient one. Before there were spaces on the page (between paragraphs, and even between words), there were symbols in the margins to let the reader know when the writer was shifting to a new idea.

I like the idea of scoping this week’s contest to a paragraph for two reasons. 1) It’s a small scope, and I hope it might trigger a daily practice where you record your ideas and thoughts as paragraphs (I recommend writing a few and submitting your favorite), and 2) It will get you to think more analytically about the atomic unit that makes up all of your writing.

My project, Essay Architecture, has caused me to think extensively about what a paragraph is. Of course, there are galaxies of possible paragraphs. Each one should be different. The commonalities between them are almost too obvious: a paragraph has a beginning, and end, and a path to get there. This sounds obvious, but

• Frame: How can the opening sentence serve as a hook? The opening of a paragraph is more than a factual summary of the information contained in it; it is often a concise statement with an embedded mystery. Orient us, while leaving something unresolved.
• Fabric: How can you build a compelling chain of sentences? If your paragraph is a single idea or scene, you can “rotate” around it to show different facets of it. As you move through ideas, consider how synonyms, transition words, and sentence forms can be used to create forward momentum.
• Finale: How can the closing sentence have power in the subtext? Some writers end paragraphs on a punchline, and others end with an emotional punch. Some paragraphs can close on an epic, long sentence, and others on a short quip, but in either case, there can be an implication that rings bigger than the words in the sentence. When you close by showing rather then telling, it gives the reader something to see, feel, and reflect on in the space between paragraphs.

Great writers aren't necessarily great educators. If you're trying to actually transfer knowledge that a stranger across space and time can realistically implement, you might need a level of explicitness that would curl and destroy a memoiristic essay. Both McPhee and Gornick feel as if they care more about their own prose than their readers ability to write prose.