Writing & Expression: Writing as a VocationThe long game · Reader relationships · The reality of publishing · Income models
BigCat's Writing
For a seasoned technologist, writing isn't "quit your job to become a novelist." It's a craft you can practice for life — and one that compounds. Today isn't about inspiration; it's about vocation: how to see writing on a ten-year timescale rather than a one-week one — how it accumulates, how it connects you to readers, what publishing really looks like, and how it actually pays (usually not the way you think).
Principle 01
The Long Game: One Post Is a Bet; a Body of Work Compounds
The Long Game — Compounding a Body of Work
Vocation · Compounding
The Principle + a Master's Words
Any single piece pays almost nothing today, but a public body of work built over a decade compounds. Don't judge writing by the fate of one post — judge it by the ten-year curve.
"How we spend our days is, of course, how we spend our lives."
— Annie Dillard, The Writing Life (1989)
A vocation is nothing but the accumulation of thousands of "did I write today?"
Why It Works
Public writing compounds on two axes. First, craft: your 200th piece will inevitably beat your 2nd. Second, assets: old posts keep getting found and cited, turning strangers into readers while you sleep. Most people quit at the "plateau" — a post gets fifty views, so they conclude it "doesn't work." The real shift is from watching "will this one go viral?" (a single point, a gamble) to watching "is my body of work growing?" (a curve, an inevitability). The opponent isn't talent — it's whether you keep shipping on time through the first two unapplauded years.
Flat for a long time — clear the "plateau" and the curve finally lifts
The Rewrite (the core)
(Short game) "My post got 12 likes. Writing doesn't work." Quit after a month.(Long game) Treat each post as a brick stored for a future reader. Set a two-year "weekly" goal; ignore per-post numbers, ask only "did I ship on time?" Post #80 is the one a stranger finds on Google — and the back catalog does the rest.
(Chasing the trend) Whatever's hot this week, I write about it — riding traffic that isn't mine and never settles into a body of work.(Building the system) Write to a durable theme I'll still care about in five years. Each piece deepens the last; the archive becomes an asset, not a pile of expired takes.
When to Use It + Common Mistakes
✓ Personal brand, thought leadership, promo evidence, long-term reach — any goal measured in years
✗ Not for: one-off, time-sensitive output (don't expect today's announcement to compound)
✗ Trap: making stay-or-quit decisions on a single post's stats — that's the gambler's mind; you'll fold at the plateau
✗ Trap: chasing trends instead of building a system — borrowed traffic isn't yours and never settles into a body of work
Key References
Annie Dillard, The Writing Life (1989) · James Clear, Atomic Habits (on compounding & systems > goals)
This Week's Exercise + a Question
Make a writing commitment measured in years (say, 12 pieces a quarter), and write down exactly how you'll ship in "week 6, when no one's watching." Question: The last time you quit writing — was it because writing truly didn't work, or because you judged a "year" project on a "week" timescale?
Principle 02
Reader Relationships: Write for One, Not for All
Reader Relationships — Write for One, Not for All
Readers · Niche
The Principle + a Master's Words
A body of work compounds, but it cashes out in reader relationships. And there's a paradox to building them: try to please everyone and you move no one; write for one specific person and a crowd gathers.
"Write to please just one person. If you open a window and make love to the world, so to speak, your story will get pneumonia."
— Kurt Vonnegut, "How to Write with Style" (1980)
Aim at one heart, and you'll reach the thousand hearts that resemble it.
Why It Works
Readers aren't "traffic" (a countable, anonymous total) — they're relationships (specific people willing to come back). Writing for "everyone" is writing for no one: you instinctively sand off every edge and end up with a piece no one dislikes and no one remembers. Write for one concrete person — a peer you respect, yourself three years ago, the reader who once asked a real question — and your tone, examples, and depth calibrate themselves, hitting a whole crowd of "people like them." That's the power of the niche: the more specific, the more resonant, the more it belongs to someone. And once built, a reader relationship is your most crash-resistant asset — platforms fold, algorithms shift, but the three hundred people who actually subscribe to you won't.
The Rewrite (the core)
(To everyone) "This guide is for anyone who wants to improve their communication skills." (Broad — claimed by no one.)(To one) "For the person I was three years ago, who wrote design docs as flat chronologies and got them bounced three times by the director." (Specific — someone recognizes themselves, and the voice warms up.)
(To everyone) "Anyone who wants to write better memos will find this useful."(To one) "For the senior engineer who writes brilliant code, then buries the point of the memo on page three." (A thousand of them nod.)
When to Use It + Common Mistakes
✓ Personal brand, a newsletter, a column — anything that lives on returning readers, not one-time exposure
✗ Not for: purely functional notices, legal terms (there, "cover everyone" is correct)
✗ Trap: treating readers as a traffic number — you chase metrics instead of relationships, and grow emptier for it
✗ Trap: diluting your view to avoid offending anyone — perfectly balanced means perfectly forgettable
Key References
Kurt Vonnegut, "How to Write with Style" (1980) · Kevin Kelly, "1,000 True Fans" (2008)
This Week's Exercise + a Question
Add a one-line "reader portrait" to whatever you're writing — not "professionals," but one person so specific you can picture their face. Question: Are you afraid of "writing for only a small group"? Is that fear a reasoned judgment, or the compulsion to be liked by everyone?
Principle 03
The Reality of Publishing: The Gatekeeper Is Dead, but No One Owes You a Reader
The Reality of Publishing — Show Your Work
Publishing · Being found
The Principle + a Master's Words
Here's the truth about publishing now: technically it's free (anyone can ship with one click), but attention is scarcer than ever — no gatekeeper, and no guaranteed reader. The way through isn't "wait to be discovered" — it's to keep showing your work so the right people can find you.
"You don't really find an audience for your work; they find you."
— Austin Kleon, Show Your Work! (2014)
You don't go out and locate your readers — they locate you.
Why It Works
In the old world, publishing was decided by gatekeepers (editors, publishers); the scarce thing was the right to publish. In the new world, that right is unlimited, and the scarcity becomes being found. Two things flip. First, you no longer need permission — you can publish today, and "ready" never arrives; maturity is what feedback grinds into you after you ship. Second, "cool" work is not seen automatically — search and algorithms favor what is continuous, indexable, and linkable. So the strategy is exactly Kleon's show your work: put the process, the notes, the half-finished pieces out there, manufacturing a large "searchable surface area" so the right person stumbles into you at the right moment. Publishing stops being a one-shot event ("finish → submit → wait") and becomes a continuous process ("keep publishing → get found → get linked → compound").
The Rewrite (the core)
(Waiting to be found) Bottle up the "ultimate long read" for six months, too scared of imperfection to ship; finally post it, then wait for it to go viral.(Showing the work) Publish one small thing weekly — a note, a teardown, a failure. In half a year you've built 25 "doors," and one of them gets found — the one you'd never have bet on.
(Waiting to be found) Polish one magnum opus for a year; ship it; wait for it to go viral.(Showing the work) Post one small thing weekly. In a year you've built 50 doors. The reader walks through the one you'd never have bet on.
When to Use It + Common Mistakes
✓ Building public reach, finding opportunities and collaborators, making your expertise searchable
✗ Not for: confidential material, or half-formed takes so immature they'd mislead (public ≠ irresponsible)
✗ Trap: perfectionism — treating "publish" as a terminal event, so you're forever "not ready"
✗ Trap: shipping only finished products, never the process — the process often builds more trust and connection than the conclusion
Key References
Austin Kleon, Show Your Work! (2014) · Paul Graham, "Writing, Briefly" (on writing a lot, in public)
This Week's Exercise + a Question
Take something you feel "isn't ready to publish," cut it down to the smallest version you could ship today, and ship it. Question: How much of your "not ready yet" is a real standard, and how much is a cover for fear of being judged?
Principle 04
Income Models: Direct Income Is the Tip; Indirect Leverage Is the Mountain
Income Models — The Tip and the Mountain
Money · Leverage
The Principle + a Master's Words
How does writing pay? Most people stare only at direct income (fees, books, subscriptions) — usually the thin tip of the pyramid. For a technologist, the real bulk is indirect leverage: reputation, opportunity, network, bargaining power — the things that turn writing into an amplifier for your career.
"Code and media are permissionless leverage. They're the leverage behind the newly rich."
— Naval Ravikant, "How to Get Rich" (2018)
Content, like code, is leverage you can pull without anyone's approval.
Why It Works
Split writing income into two tiers. The tip is direct income — books, columns, paid subscriptions, courses; real, but thin and slow for almost everyone (Kevin Kelly's "1,000 True Fans" is the optimistic ceiling of this tier). The base is indirect leverage — one widely-shared technical post can become hard evidence in a promo packet, a bargaining chip when you switch jobs, a conference invite, a future co-founder, pre-established trust when you hire. For a technologist with a day job, the rational model isn't "quit to write for money" — it's "writing is a near-zero-marginal-cost lever that compounds the expertise you already have." Naval's keyword is permissionless: unlike capital and labor, which need sign-off, you can pull this lever tonight. Chase the leverage first, and direct income tends to show up on its own, as a by-product.
the mountain — for a technologist with a job, this is the bulk
Don't measure the whole mountain with the tip's tiny ruler
The Rewrite (the core)
(Cash only) "Writing doesn't pay — $50 a post, less than overtime." So he never writes.(Leverage) That post explaining your system-design tradeoffs paid $0 in fees; but it went into your promo packet, got reshared by the CTO, and led to a conference talk. A year on, it was the best-ROI hour you spent.
(Cash only) "Writing pays $50 a post. Overtime pays more." So he never writes.(Leverage) The post earned $0. It also became Exhibit A in his promo packet, got reshared by the VP, and turned into a conference talk. Best-paid hour of his year — just paid on a delay.
When to Use It + Common Mistakes
✓ Technologists and leaders with a day job who want to amplify their expertise — writing as career leverage
✓ On the path to an "AI-powered individual": content is zero-marginal-cost, permissionless leverage
✗ Trap: measuring writing only by direct fees, so it always seems "not worth it"
✗ Trap: reaching for a paywall on day one — build trust and readers first; money is a lagging by-product
Key References
Naval Ravikant, "How to Get Rich" (2018) · Kevin Kelly, "1,000 True Fans" · Paul Graham, "How to Make Wealth"
This Week's Exercise + a Question
Take one piece you've written (or want to write) and list 3 "indirect returns" it could bring beyond any fee (opportunity / trust / network). Question: Have you underrated writing — and kept putting off the pen — because you only ever kept the "direct fee" ledger?
The Vocation, in One Line
The vocation, in one line
All four point to one thing: treat writing as a craft measured in decades and built to compound, not a one-shot bet. The long game decides whether you outlast the unapplauded plateau; reader relationships cash a body of work into your most crash-resistant asset; facing the reality of publishing makes you stop "waiting to be found" and start "being findable"; understanding income models keeps you from measuring writing with the wrong ruler. As a vocation, writing never pays in instant applause — it pays when you look back after ten years and find you own a body of work no one can take, a crowd of real readers, and a life your own words have amplified.
Deeper question 1: Can "the long game" curdle into stubbornness-as-self-flattery? How do you tell a plateau worth enduring from a dead end you should cut?
The tell is process feedback. A plateau worth enduring: your craft is visibly improving (you cringe at pieces from three months ago), the occasional reader responds in depth, and you still have things you want to say. Signs to cut: two years in with no craft gain (repetition, not deliberate practice), content you don't even believe, grinding purely for metrics. What you persist in should be the sharpening of a craft, not an obsession with numbers. Use "am I getting stronger?" — not "did I go viral?" — as the basis for continuing.
Deeper question 2: Doesn't "write for one" clash with wanting reach? You want to move many, yet speak to one?
No clash — it's the path. Reach isn't the result of shouting at everyone; it's the accumulation of deeply moving one person, of whom the world holds many. Broad flattery dilutes the signal; precise resonance replicates itself — the person you hit passes it on. To reach a million, the fastest route is to genuinely move one, then trust that "people like them" are plentiful.
Deeper question 3: Has "zero-barrier" publishing devalued writing? If everyone can post, can anyone be seen?
Publishing got cheaper; judgment got dearer. When supply is unlimited, the scarce thing is no longer "can you post" but "is it worth reading" — sincerity, depth, a distinct viewpoint, trustworthy judgment are scarcer and more valuable than ever. Zero barriers wash out those who lived on monopolizing the right to publish, and reward those who keep providing real value. For a technologist with something true to say, this is the best era there's ever been.
Deeper question 4: If AI can generate an essay with one click, does "writing as a vocation" still hold? Will the craft be ended by AI?
What ends is "writing as manual labor" (generic, replaceable prose with no personal judgment); what stands out is "writing as thought and character." AI can generate a competent average, but reader relationships rest on trusting one specific person's judgment and taste — precisely what can't be outsourced. The vocation's core was never "typing words" but "having something worth saying, and daring to vouch for it under your own name." Use AI as an accelerator (to challenge, retrieve, polish); don't let it replace the judgment core that makes you you. (Echoes Day 59's tool discipline and Day 14 on AI writing.)