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Writing Craft

Writing is not merely communication for Jason — it is the primary tool for clear thinking, personal development, and building a public intellectual practice. From Ben Putano's "Great Founders Write" cohort to early feedback on a first book manuscript to the mechanics of pitching major publications, the collected notes on writing craft converge on a single argument: the quality of your writing is inseparable from the quality of your thinking, and both compound over time in ways that most other skills do not.

Writing as Thinking

The foundational claim, borrowed from William Zinsser via Ben Putano: "Clear thinking is clear writing. One cannot exist without the other." This sounds like a truism until you watch someone who is bright and articulate in conversation produce muddled prose. The reason is that spoken conversation lets you iterate in real time — you can see your listener's face, backtrack, rephrase, use gesture. Writing strips all of that away. The sentence either works or it doesn't.

For founders and knowledge workers, this creates a specific kind of leverage. In a remote, globally distributed economy, written communication is the primary mode of influence. You cannot rely on charisma, timing, or the energy of a room. What you send is what people have. Jason's participation in the Great Founders Write cohort (run by Ben Putano) reinforced this: writing forces externalization of thinking that would otherwise stay trapped — and once externalized, it can be refined, shared, and built upon.

There's also a compounding argument. Writing multiplies opportunities in ways that a single conversation cannot. A well-crafted post, essay, or thread reaches people you've never met, at times you're not present, in contexts you didn't anticipate. Paul Ford wrote 40,000 words for Bloomberg only after breaking through months of procrastination — the piece became a landmark in tech writing. The value was not proportional to the effort of any single session; it was proportional to the total output that finally existed.

Craft Principles

Specificity Over Abstraction

This is the single most consistent principle across all writing-related notes, appearing in sources as different as Stanford admissions advice, copywriting courses, and business writing frameworks.

The mechanism is attention. Abstractions slide past the brain. Concrete images and specific details stick because the brain is wired to process sensory information — it knows what to do with a journalism ID badge but not with "a formative experience that taught me about professionalism." Stanford admissions essays that worked used concrete subjects: a tennis practice, a crossword puzzle, a specific conversation. Essays that tried to argue for abstract qualities ("leadership," "resilience") came across as preachy rather than persuasive.

David C. Baker's "Business of Expertise" makes the same case for nonfiction: the specific, counterintuitive detail is what earns and holds attention. Generic advice is instantly forgettable because it could apply to anyone. The more precisely you write for a specific person in a specific situation, the more universally it lands — because everyone else recognizes the specificity as evidence of genuine understanding.

"Tell, don't explain" is the shorthand. Essays that explain their own significance — that tell you this was important rather than putting you inside the moment — come across as preachy. Show the scene and trust the reader to feel it.

Voice and Authenticity

Voice emerges from accumulation. You cannot decide to have a voice; you develop one by writing a lot, reading writers you admire, and noticing what resonates with readers when it's yours vs. when it's borrowed. The early feedback on "Unstoppable" (Jason's first book) was consistent: more personal stories, less abstract framework. The blog's strength was its personal specificity — the voice people followed was recognizable and human, not authoritative and distant.

One recurring description of what works: "Posts that were personal, informative and actionable. Or if not actionable, inspiring." The conjunction matters. Purely informational writing becomes a commodity. Purely personal writing becomes navel-gazing. The combination — here is something real about my experience that you can also use — is what builds genuine readership.

Clear Over Clever

From multiple sources (Eddie Shleyner's copywriting course, Brand Builders Group's "Wealthy and Well-Known"): clarity outperforms cleverness every time, especially in titles and headlines.

The "I Want Blank" test: insert your title into the sentence "I want ___" and see if it completes coherently and compellingly. "I want Good to Great" works. "I want Procrastinate on Purpose" doesn't — and the data bore this out. Rory Vaden's book on the clearer topic consistently outsold the one with the more abstract title, despite the latter containing more original ideas.

The clarity continuum runs from Confusing to Intriguing to Enticing to Irresistible. Intriguing is not good enough — "I wonder what that means" is not the same as "I need that." The goal is irresistible. Titles that pass the "I Want Blank" test, signal positive energy (expansive, abundant words over negative or neutral ones), and use the target reader's native vocabulary — their insider terms and familiar phrases — dramatically outperform clever alternatives.

Justin Welsh credits this clarity principle for $2.8M+ in course sales. The principle scales down to every level of writing: email subject lines, LinkedIn posts, article subheadings.

Speed and Imperfection

"If it's worth doing, it's worth doing shitty now and improving as you go." The enemy of writing is perfectionism, which masks itself as quality control but is usually fear. Perfectionists produce less, which means they improve more slowly, which means they have less material to work from. The cycle is self-reinforcing in the wrong direction.

The counterintuitive claim: readers almost always want more rather than better. More specificity, more story, more of you — not more polished and less human. The missing chapter in "Unstoppable," identified by early readers, was "what if it all goes wrong?" — a more vulnerable, less curated perspective that would have made the whole manuscript more credible.

Getting Published

Pitching Publications

Publication pitches fail for predictable reasons: they're too long, they don't establish urgency, they target the wrong person, or they don't demonstrate knowledge of the outlet's existing categories.

The mechanics that work:

  • Keep pitches short. The Guardian wants two paragraphs maximum. HBR wants a short outline first. Length signals that you don't understand their time constraints.
  • Explain why this piece is urgent right now — what just happened, what trend just crested, why the timing is not arbitrary.
  • Match the outlet's existing structure. HBR runs pieces organized around specific management questions; a pitch should mirror that. The Guardian Opinion runs first-person essays on specific current events; pitch the angle, not the topic.
  • Go to section editors directly, not generic submission forms. Generic forms reach nobody in particular.
  • For HBR specifically: What is new or counterintuitive? Why do managers need this right now? What is your source of authority on the subject?

The Pitching Lenny example illustrates the pitch format that works: warm connection, clear topic with a specific hook (Medium hit 1M paid subscribers + breakeven), named interview subjects (CEO Tony Stubblebine already confirmed), comparable prior work, and a clean ask. It's a paragraph of credibility, a paragraph of content, and a paragraph of invitation.

Book Publishing Reality

The data from the DOJ vs. Penguin Random House antitrust trial is clarifying in ways that are uncomfortable for anyone with traditional publishing ambitions:

  • 96% of books sell fewer than 1,000 copies
  • 50% of titles sell fewer than a dozen copies
  • 2% of titles earn advances over $250,000; 85% of those never earn out
  • Billie Eilish (97M followers) sold 64,000 copies — a massive platform does not translate automatically to book sales
  • The Big Five publishers operate like VCs: many small bets, most of which fail, sustained by rare "gushers" (Twilight, Fifty Shades of Grey, Colleen Hoover) that come along every five to ten years

The implication is not that books are pointless — it's that the mental model of "write a book, get published, build an audience" is backwards. The audience comes first. Publishers want built-in audiences because that's how they reduce risk. A Substack with 20,000 engaged subscribers is more valuable to a publisher than a manuscript alone.

For writers who want to reach readers without playing the traditional odds, Substack, direct-to-audience models, and platform-first thinking are rational alternatives — not consolation prizes.

Query Letters

The standard nonfiction query letter format:

  1. Hook and concept — your setup, the title and proposed word count, and what makes this urgent. If it reads like a textbook, you've already lost.
  2. Credentials — qualifications, experience, prior publications, anything that answers "why is this person the right author." For nonfiction, author platform and media exposure are treated as near-equal to writing quality.
  3. Competitive differentiation — how your book differs from comparable titles. Never claim yours is the first on the subject; it isn't.
  4. Invitation — ask for representation, state how long completion will take. For nonfiction, a completed manuscript is not required — a well-constructed proposal suffices.

The author bio and media exposure carry more weight than most writers expect. Agents and editors are also salespeople; they need to believe they can sell you to their acquisition committee, and they need to believe your book is promotable. Credentials are evidence that it is.

Book Projects

"Prime Time" (30s Book)

The core thesis: your 20s are about living in a way that "looks good" (external validation, mimetic desire — chasing prestige because everyone around you is chasing prestige). Your 30s are the first chance to live in a way that "feels right" (intrinsic interest, personal values). The shift is partly developmental: the prefrontal cortex finishes forming in the late 20s, meaning thirty-year-olds literally think differently — with more capacity for nuance, long-term planning, and genuine self-knowledge.

The book's Four A's Playbook (Agency, Authorship, Attunement, Acceptance) provides a framework for the transition. The target reader is an achievement-oriented millennial or Gen Z professional who has done many things "right" and still feels off — what the book calls the "blah" of early established adulthood, when the career is okay and the relationships are okay but something isn't clicking. The diagnosis is that they've been running someone else's race.

The structural challenge the book addresses: the 30s are a transition period with compounding consequences. Dating pools change significantly by 40. Career changes in your 30s still leave decades to develop in a new direction; career changes in your 50s don't. Physical investments that were optional at 25 become non-negotiable at 35. The urgency is real, and the book earns its focus on a specific decade rather than offering timeless advice that applies everywhere and grips nowhere.

"Unstoppable" (Early Work)

The earliest completed book manuscript. Feedback from early readers converged on several consistent points:

  • Go deeper, not broader — depth over breadth signals conviction and serves readers better
  • Personal stories sell ideas; the framework only works when a human experience is underneath it
  • Concreteness beats inspiration — specific moments and outcomes more than abstract encouragements
  • The missing chapter was "what if it all goes wrong?" — resilience in the face of actual failure, not just general resilience

These notes shaped subsequent thinking about the craft: a book that doesn't risk something personal doesn't earn the reader's trust.

The WhatsApp Group Story

A pivotal moment in the writing life: completing Kelly's 30-day book writing cohort, being invited to join an exclusive creator WhatsApp group (Tiago Forte, Nat Ellison, others), spending days crafting a bio, and then having the invitation rescinded — someone in the group had objected, for reasons never disclosed.

The moment was painful in a specific way because the book itself was about being an outlier and the difficulty of finding belonging. To be rejected from a belonging-space in that exact moment had the texture of dark irony.

The resolution came slowly: the purpose of writing is not to gain admission to existing circles but to create spaces where others can belong. The next keystroke after a rejection is a small act of defiance and a bridge to unknown readers. "The best way to find belonging is to create it yourself, one word at a time."

The Ladder of Abstraction

Roy Peter Clark and Tomas Alex Tizon's essay "Every Profile Is an Epic Story" distills S. I. Hayakawa's ladder of abstraction into a working instrument for narrative journalism. Hayakawa's 1939 formulation (from Language in Thought and Action) imagines meaning as a ladder: the concrete, sensory particulars of an event sit at the bottom; the abstract generalizations that draw meaning out of those particulars sit at the top. A stool has four legs, two feet tall, pine — that's the bottom. "Furniture" is higher. "Assets" is higher still. At the very top sit categories like "value" or "justice" that have no sensory content at all.

Clark and Tizon's claim is that the best narrative writing moves fluidly up and down the ladder within a single piece. You open with a specific image — a boy running up a flight of stairs, a man folding a paper crane, a sound from a particular doorway at a particular hour — and then, without abandoning that specificity, you climb to meaning. The meaning lands because it is tethered to the concrete. Then you descend again, to another specific image that shows the meaning in action, and climb again, slightly differently. The movement is the craft.

Writers who stay at the bottom produce journalism that is vivid but inert — all color, no weight, readers unsure why they're being told this. Writers who stay at the top produce essays that are abstract and forgettable — all argument, no grounding, the reader skimming for a concrete moment that never arrives. The latter is the more common failure mode for ambitious nonfiction writers, particularly coaches, consultants, and intellectuals whose professional discourse runs in abstractions. The signal of this failure: the piece is "interesting" but the reader can't quote a single sentence back.

For Jason's work the ladder is the explanatory frame for a pattern his editors and readers have been pointing at for years: "the framework only works when a human experience is underneath it" (from the Unstoppable feedback), "Tell, don't explain," the insistence on opening anecdotes followed by principle. These are all ladder moves. The opening anecdote is the bottom rung — a specific client, a specific conversation, a specific moment at a specific time. The reversal move, where the apparent lesson flips into its opposite, is the climb up. The declarative hammers that close sections are the top-of-ladder meaning. The next anecdote drops the ladder back down. This pattern, documented in jason-voice-and-style, is the ladder being walked.

Clark and Tizon give two practical tests for whether a passage is working. First, the specificity test: can the reader see what the writer saw? If the verbs are vague and the nouns are categorical, the writer has parked at the top of the ladder. Second, the meaning test: does the specificity carry weight beyond itself? If not, the writer is at the bottom with no climb — pure description, forgettable. Good narrative passes both tests simultaneously: each specific detail carries meaning because the writer has moved up and back down the ladder enough times that the pattern of ascent is practiced.

The ladder also clarifies what paul-graham-influence is doing. PG's essays open with a concrete observation (a conversation at YC, a pattern in a batch of applications, a specific startup's trajectory), climb to an abstract principle that names the pattern, and descend again with a second or third specific application. The rhythm is the ladder. The reason PG's prose is so transmissible — quotable, citable, memetic — is that the abstract principles are always grounded in specific cases, so readers have both the label and a concrete referent.

For drafting, the ladder suggests a self-edit pass. Read the draft and mark each paragraph as "bottom," "middle," or "top" rung. If three consecutive paragraphs are all top-rung, the reader is lost — add a specific scene. If three consecutive paragraphs are all bottom-rung, the meaning is absent — add a line that names what the scene is showing. The movement is the craft.

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