This is a retrospective episode of the How I Write podcast, where the host recaps lessons learned from interviewing 20 master writers over roughly 20 episodes. He shares both on-record insights and behind-the-scenes stories, reflecting on how these conversations have reshaped his own writing process and the mission of his company, Write of Passage. The overarching theme is that there is no single “right” way to write—great writers succeed by finding their own distinctive approach and executing it at an exceptionally high level.
Tim Ferriss: Low bar for inputs, high bar for outputs
Ferriss’s core writing habit is to write just two crappy pages per day—a deliberately low bar that removes the pressure of quality during the drafting phase and builds consistent momentum.
Despite the low input bar, his output quality bar is extremely high: he refines relentlessly because a book stays with you for decades, and publishing a mediocre one is worse than publishing nothing.
He has two of the top four bestselling Kindle books of all time (4-Hour Body, 4-Hour Chef), behind only the ESV Bible and The One Year Bible.
Practical feedback technique: when asking friends for feedback, he asks two questions—“What 20% should I keep no matter what?” and “If I had to cut 20%, what should it be?” This psychologically softens harsh criticism by sandwiching it between genuine praise.
Hire a law student or lawyer to edit your writing: lawyers are trained to spot ambiguity and weak arguments, making them ideal editors for tightening logic and eliminating vulnerabilities in your prose.
Kevin Kelly: Don’t aim to be the best—be the only
Kelly’s maxim from Excellent Advice for Living: “Don’t aim to be the best, be the only.” The breakthroughs happen when you’re doing something so unique there isn’t even a name for it yet.
He openly acknowledges the trade-off: by following his obsessive curiosity across many domains rather than focusing narrowly, he “wasn’t able to be great” in the conventional sense—he didn’t build a massive company or write a single blockbuster book.
His physical studio in California is a multi-story celebration of his passions—thousands of books, taxidermy, hand-built objects, biology specimens, Asian photography—a space that only Kevin Kelly could have built, mirroring how he tries to write pieces that only he can write.
He lives by alignment: his head, heart, and wallet all point in the same direction. Productivity, he says, is often a distraction—“look for writing projects you never want to stop doing.”
The host’s broader takeaway: surrender to your nature. Quality without distinctiveness produces derivative work; distinctiveness without quality produces shock value. The goal is both, and that requires deep self-knowledge.
Cultural Tutor: Read what nobody else is reading
The Cultural Tutor went from working at McDonald’s to 1.6 million Twitter followers in about 1.8 years, supported early on by the host as a patron.
His core reading rule: “If it was published in the last 50 years, don’t read it.” The reasoning is not that new books are bad, but that everyone else is reading them—so consuming them gives you no distinctive edge as a writer.
He treats reading as choosing the soil from which your ideas will grow. Reading Boethius’s Consolation of Philosophy (a bestseller for 1,200 years) instead of Atomic Habits means your ideas will be fundamentally different from everyone else’s.
Even if an old book is flawed, its influence over centuries means reading it gives you deep insight into how the world’s worldview was shaped.
The host sees this as an antidote to the internet’s “never-ending now”—the algorithmic bias toward recency that traps everyone in consuming the same 24-hour news and content cycle.
Marc Andreessen: The barbell approach to information
Andreessen uses a barbell strategy: consume either super-current information (Twitter, group chats, conversations with experts) or timeless material (history, biography, old books). He deliberately screens out everything in between—roughly the last 1 to 10 years.
This contrasts with Cultural Tutor’s approach (ignore the last 50 years) but shares the same logic: avoid the undifferentiated middle where everyone else’s attention is focused.
Behind-the-scenes: the host accidentally shattered his mother’s vase transporting it to the Andreessen Horowitz set for the interview, then spent 3.5 hours decorating the recording space to match the show’s signature aesthetic.
Riva Tez: Writing as word painting
Tez thinks of writing not as logical argument but as “word painting”—creating a pre-ordered mood, much like pointillism, where individual dots of color only cohere into a beautiful scene when you step back.
She leans into feeling deeply rather than arguing logically. Her passion and sensitivity produce distinctive language naturally—she doesn’t need a thesaurus because the vibrancy comes from genuine emotion.
Her method rejects daily discipline in favor of fanatical obsession: she waits until she feels a strong desire to write, then clears her calendar for days, drives to a remote location (like Joshua Tree or Yosemite), and writes without stopping until the project is done.
She cites Feyerabend’s Against Method as an influence—choosing creative bursts over moderation.
The host studies her sentences in an Evernote document and uses them as models to push his own writing toward more emotional resonance.
Steven Pressfield: Immense care for the craft
Pressfield has been writing seriously for 50 years; he tried to publish his first novel at 22–23 but didn’t succeed until his 50s—30 years of struggle that deepened his devotion to craft.
He drove one hour each way to hand-deliver a copy of his new book to the host the day before their interview, refusing to use a courier because the book was “too important.”
His signature principle: “The female carries the mystery.” In story, the feminine element (a woman, the sea, the desert, the rice fields) carries the unsolvable mystery at the heart of the narrative. In Moby Dick, the sea is the female; in Lawrence of Arabia, the desert is the female; in Seven Samurai, the rice fields are the female. The mystery is always something that cannot be solved—it points toward God, creation, life itself.
The host describes hearing Pressfield explain this as akin to hearing Tiger Woods discuss a golf swing—a revelation of deep expertise that recontextualizes everything.
Tyler Cowen and Alex Tabarrok: Joy as a competitive advantage
After 20 years of working together on Marginal Revolution, Cowen and Tabarrok still radiate genuine joy and laughter in their intellectual partnership—something the host deeply aspires to.
Cowen is driven by what’s fun: “Most other people don’t find it that fun. So it’s a competitive advantage just to be choosing things you’re intrinsically interested in.”
He obsesses over craft at scale: if a piece takes each of his 50,000–100,000 readers one second less to read, that’s a socially worthwhile return on the time he spent tightening it. He calls MR “dim sum for the mind.”
The host admires Cowen’s total alignment between head, heart, and wallet—his curiosities, his income, and his service to the world all flow in the same direction, producing a lifetime of output that feels like “motion without force.”
Ava Huang (N Bombsky): Reaching beyond consensus
Huang’s core principle: never write anything that is a cliché. When she recognizes a sentence as recycled or rote, she forces herself to find a fresh way to say it.
The host frames writing as excavation: the first ideas that come to mind are usually the most clichéd—the “dirty water” at the start of the creative faucet (borrowing Ed Sheeran’s analogy). You have to keep writing, digging through drafts, until the clean, unique water flows.
Writing is vertical; thinking is thinking is horizontal. The mind naturally skips across topics (like lily pads), staying surface level. Writing chains you to one idea, forcing depth and rigor that unstructured thinking cannot achieve.
The host’s key insight: whenever his thinking feels superficial, it’s because he hasn’t written enough about it. Writing is the anchor that transforms shallow thoughts into rigorous ones.
How the podcast changed the host’s mission
The host is pivoting Write of Passage’s mission from “help people publish consistently and build a writing habit” to “help people find, publish, and share their core idea”—and make it the best thing they’ve ever written.
Inspired by Tim Ferriss’s argument that the returns to volume are collapsing (due to AI and the flood of weekly newsletters), while the returns to genuine quality are as high as ever.
He wants to help people write one excellent piece that reaches 10,000 readers and changes their life, rather than writing hundreds of mediocre pieces over years.
He’s drawn to the Greek concept of archigos (author, founder, pioneer, leader—all the same word): writing is the seed from which founding, pioneering, and leading naturally grow. Examples include Marc Andreessen (who recruits and builds through writing) and America’s founding fathers (who wrote the Constitution, then founded a country, then led it).
His goal: every piece that comes out of Write of Passage should reach 10,000 readers, developed through intensive coaching and editing—applying the same intensity he brought to competitive golf and to producing the podcast.
Final reflections
The host initially expected to discover one correct way to write. Instead, he found that every great writer has a different method—what unites them is being exceptionally good at whatever distinctive approach they’ve found.
His advice to listeners: don’t try to implement everything you hear. Treat the podcast like thrift shopping for ideas—pick what resonates, discard what doesn’t, and gradually assemble your own approach to the craft.
