CaddieOpen in CaddieDownload for Mac

How to sound like yourself on the page

Shared by Caddie Library · Updated
Chapters show their main points
Chapter 18 of 20 · Clear Sentences and Voice
← The growth course
1. Finding Product-Market Fit
Test for real customer pull earlyPick a narrow niche to start inLaunch a simple first version fastLearn from users and customersRead early signs of product-market fit
2. Onboarding and Activation
Structure onboarding as a storyAsk and use onboarding questionsGet users to the aha moment fastDecide how long onboarding should beBuild quiz funnels for paid traffic
3. Paywalls and Pricing
When to choose a hard paywall over freemiumDesign a paywall that convertsPrice annual and monthly plansSet, raise and localize pricesRun free trials and free tastes
4. Business Models and Revenue
Structure subscription tiersKeep a free tier that pays offCharge for usage and AI creditsPair hardware with a subscriptionAdd ads, affiliates and partners
5. Retention and Engagement
Measure retention honestlyBuild habit loops that bring users backUse notifications and lifecycle messagesReduce churn and handle cancellationsBuild social loops and community
6. Brand and Positioning
Position against bigger incumbentsName and describe your productEarn trust in high-stakes categoriesBorrow credibility from celebrities and experts
7. Organic Content and Creators
Find, vet and recruit creatorsPay creators fairly and safelyBrief and manage creatorsFind and copy viral formatsScale one format across many accountsRank in AI search and SEO
8. Paid, App Store and Viral Growth
Make ads that convertTurn organic winners into paid adsStructure and scale Meta campaignsTell if paid acquisition is profitableWin in the App StoreBuild viral and referral loops
9. Experimentation and Analytics
Run trustworthy experimentsJudge test results correctlyRun more experiments fasterWhat metrics to track and how to define them
10. Building AI Products
Build for the models of tomorrowDesign AI interfaces beyond chatDesign AI agents people can trustMeasure AI quality with evalsControl AI costs and pricingBuild products with AI coding tools
11. Teams, Hiring and Funding
Hire people who thrive on ambiguityOrganize small product teamsRun exploratory bets and kill themWork as a team with AI agentsWhen to raise money or sell your company
12. Founder Principles
Pick a mission worth building a company aroundWhy to trust your own judgment over the consensusTurn failure and setbacks into the next stepLearn from rivals and copy what works
13. Choosing Where to Compete
Make low cost your competitive advantageCreate a market instead of fighting for shareWhy scarcity and brand can beat volumeBuild an advantage that feeds itselfAttack a bigger rival where it cannot followWhen to stay focused on the core business
14. Building and Leading the Company
Hire great people and give them roomAlign pay and ownership with the missionKeep your culture and standards as you growBuild candor and fast decision-makingWhy leaders must stay close to the work and customersChoose and prepare a successor
15. Capital and Deals
Fund growth without losing controlAcquire companies and keep what makes them workWhat to do with cash: reinvest, buy back or holdWhy to keep a cash cushion and avoid heavy debtStructure ownership to protect your missionNegotiate deals that keep your leverage
16. Finding Ideas and Thinking
How to find ideas worth writing aboutWhy writing is how you find out what you thinkHow to research so the writing carries feelingHow to read like a writer
17. Structure and Argument
How to open so readers keep goingHow to find the shape before you draftHow to keep readers curious with questions and cluesHow to argue without preachingHow to end so the last page lingers
18. Clear Sentences and Voice
How to write plainly for a reader who knows nothingHow to choose specific details over generic onesHow to sound like yourself on the pageHow to shape rhythm and phrases people remember
19. Characters and Storytelling
How to build characters readers care aboutWhat makes a scene move: want, obstacle and changeHow to write dialogue that sounds real but stays shortHow to make readers feel without telling themHow to turn information into a story
20. Revising, Habits and Readers
How to cut and rewrite your own draftHow to get feedback you can useHow to build a writing routine that lastsHow to get unstuck when a draft stallsHow to use AI without losing your voiceHow to write for one specific reader

1 The bottom line

Sound like yourself by writing the way you speak, learning from many writers you love, and saying what is true, even when it is embarrassing. Readers trust a real person more than a polished performance.

2 Key takeaways

  • Draft the way you talk. Speech gets past the pretending that school and "writer brain" teach.
    • Howard Marks12:55 aims for contractions, common language and simple words, so there is no barrier between him and the reader.
    • Tim Ferriss's first drafts of The 4-Hour Workweek failed when he tried to sound smart, then funny. The third worked when he wrote as if two glasses in with friends11:56.
  • Let the voice emerge instead of building it. A voice you force reads as try hard.
    • Byrne Hobart23:08 says a deliberately distinctive voice is "very try hard and embarrassing at first."
    • Tim Urban1:53 wrote about 300 posts on his first blog without trying to be a good writer, and found his voice by playing.
  • Feed your voice with several writers you love. A mix of influences becomes yours. One influence becomes an imitation.
    • Steven Johnson1:23:05 wrote college papers in the style of Foucault, then Spivak, and his own voice came out of the mix.
  • Show your weakness, not your polish. Readers identify with shared flaws and then believe your strengths.
    • Ted Gioia14:57 published the story of cops arresting him because he was too slow to work out why an alarm went off.
  • Stop writing for an imagined audience. The need to be liked drains the draft and pulls you off your own voice.
    • After reading every comment on roughly 4,000 posts, Morgan Housel29:19 decided to please one person, himself.

The only style worth having is the one you can't help.

Paul Graham, Hackers and Painters

2.1 Drop the persona and the audience

A voice goes false the moment you write to impress, to be liked or to protect an image.

  • Write for yourself, not for a crowd. Morgan Housel29:19
    • Ask whether you like the story and whether the joke makes you laugh. If so, it is good enough.
    • Henrik Karlsson33:36 spends at least half his days offline. He writes on paper or dictates while walking, so he forgets anyone will read it.
    • Housel says his best work came when he was not thinking about the audience at all. Roughly 1% of what he has written was edited by someone else.
    • Karlsson cites David Foster Wallace on 90% of writing being driven by an overwhelming need to be liked.
  • Resist both the urge to be liked and the urge to look serious. Matt Haig23:47
    • Aim for an inner voice that is immune to both temptations.
    • Lee Child31:35 quotes David Mamet: the less you worry about being liked, the more people like you.
    • Haig's first three novels came from a highbrow publisher and were self-consciously literary, which kept him from being himself.
    • Mamet was describing actors like Gene Hackman and Lee Marvin, who weren't needy.
  • Don't ask what your brand would say. AJR5:42
    • Ask instead what is embarrassing or true for you right now.
    • They say that when they pretended to be cool, like wearing metaphorical sunglasses on stage, they just looked like they were in costume.
    • Jerry Seinfeld25:40 gave Mark Normand the same note: don't show them you're doing comedy, just act natural.
  • Come across as the person you really are. Fareed Zakaria21:10
    • Aim for "let me tell you what I'm thinking," as one part of a conversation.
    • He avoids the clipped anchor voice and the brilliant Oxford debater style, even though he can do both. He thinks audiences want a human being, and that this builds more trust than a one-liner.

2.2 Draft the way you speak

Speak it first, then write what you said
Each step keeps the draft coming from passion rather than fear of what readers will think.

Say it out loud first, and your sentences lose the stiffness that writing adds.

  • Say the story out loud, then write down what you said. Shaan Puri15:00
    • State what the story is, what makes it interesting, where it starts and where it ends. Then write that.
    • Use parentheses like asides, and line breaks like dramatic pauses.
    • Ferriss composed in an email box because a Word document felt formal. He moved the text into the real editor once he had momentum.
  • Compose aloud, on a walk, and capture it. David Whyte7:58
    • He mutters or declaims lines while walking, then speaks them into his phone so he doesn't have to memorize them.
    • Chamath Palihapitiya36:49 was urged to record himself walking and talking, transcribe it, and write from the transcript. The aim is a first draft that comes from passion, not fear of what everyone will think.
    • Chamath says his Quora answers from a decade ago were raw and personable, and that his writing has since become guarded.
    • Whyte points to Wordsworth, who composed without paper and trained a little dog to run 50 yards ahead to warn him of locals.
  • Use the words you would use in conversation. Howard Marks12:55
    • Choose contractions and simple words over sophisticated ones when the meaning survives.
    • Lulu Cheng Meservey told a friend his tweets read like a hollow husk of himself31:53. His texts and lunch talk had far more substance and vigor, so she told him to write like that.
    • Readers told Marks he makes sophisticated concepts clear. One compared his writing to Einstein's "simple" level of intelligence.
    • Ward Farnsworth59:34 says to become more eloquent by reading people who talk well, not by borrowing their moves.
  • Write for the ear, with the rhythm of speech. Brandon Stanton50:43
    • Spoken word has less ornament, more repetition and more jumping around. That makes it feel like it is being said for the first time.
    • Robert Greene30:29 thinks orally and hears his sentences as he writes, so he gets strings of commas and an "and" dropped in. When a rhythm is awkward and does not communicate, he takes it out.
    • Stanton wanted the first-person prologue of Dear New York to match the texture of the 500 interview stories around it.

2.3 Feed your voice with writers you love

Many influences make a voice; one makes an imitation
Borrow single moves from many writers and the blend becomes unmistakably yours.

Absorb many influences on purpose, and use them to become more yourself, not to copy one person.

  • Imitate deliberately, from several sources. Steven Johnson1:23:05
    • Write in the style of one writer, then another, and let your own voice come out of the mix.
    • Steal single moves. He took the short, punchy button ending after long sentences from Malcolm Gladwell.
    • He had not written a five-word sentence in about 15 years until he saw Gladwell do it.
  • Mix unlikely sources and study what moves you. Noah Hawley53:14
    • His voice came from science fiction, British comedy records, New York wise-guy humor, DeLillo and Vonnegut.
    • He reread Vonnegut before writing Anthem, to learn how to be a narrator inside his own book.
    • He learned to write by writing a terrible book and then a less terrible one, with no MFA or film school.
  • Don't try to out-do the writer you admire. Position against them. Packy McCormick13:16
    • He admired Ben Thompson but knew he could not out-Thompson him, so he counter-positioned with jokes, pop culture and odd topics.
    • Peter Attia52:24 says he could never write like Sam Harris, so he set out to capture his own voice as well as he could.
    • McCormick's first ten essays each paired a pop culture reference with a business or technology idea. One compared creative destruction to the Mickey Mouse Club.
    • Attia aimed above USA Today and nearer the Wall Street Journal, but readable by a high schooler.
  • Read outside your genre while you draft. Jodi Picoult29:43
    • She avoids books in her genre, or by writers who sound like her, so she doesn't parrot them without meaning to.
    • She reads something very different instead, such as a romance.

2.4 Say what is true, including what is embarrassing

Honesty is what makes a voice interesting, and the line you are afraid of is usually the one worth keeping.

  • Keep the story you are most afraid to tell. Rob Henderson20:07
    • If a memory made him feel vulnerable or afraid of looking weak, he kept it. The stronger the fear, the more likely it stayed.
    • Tom Junod50:58 writes the line he feels he should not, then builds the story to live up to it. You may cut the line, but it makes timid writing impossible.
    • The rehab chapter and the parking lot scene were the hardest for Henderson to include. Both made it into the book.
    • Junod tried this on The Falling Man, a photo and a subject the whole country had looked away from.
  • Write from your weaknesses, not "look how cute I am." Michael Jamin13:46
    • Write from your mistakes and apologies. Readers respond to "look how human I am."
    • Ted Gioia14:57 deliberately tells stories where he said or did the wrong thing. A writer who exposes his frailties earns your trust on other topics.
    • Johann Hari35:58 confesses doubt to the reader on the page. Admitting uncertainty persuades more than performed confidence.
    • Dana Gioia45:10 says writers go dull by wanting to look good from every angle. It took him twenty years to write about his ugly, second-rate urban upbringing instead of Frost's birch woods.
    • Hari put off visiting Portugal for Chasing the Scream because he feared decriminalisation hadn't worked there either, and he told the reader so.
  • Take a stance and state it plainly. Ben Thompson36:17
    • Write "A happened because of B, because of C." Hedging every claim makes writing uninteresting.
    • Tom Segura2:36 says indifference is never funny. Be annoyed, or be delighted, but commit to an opinion.
    • Thompson admits he sometimes leaves himself an out, and accepts the risk of looking wrong.
    • Segura's example is his annoyed 7-year-old, who complains about a table in the middle of the room.

2.5 Revise toward your voice, not away from it

Make the voice natural in revision, then protect its oddness from tools and tidy advice.

  • Expect a natural voice to be made in revision. Francine Prose34:00
    • A casual, intimate voice does not have to arrive in draft one.
    • Anne Frank heard a radio broadcast about publishing wartime accounts, then went back and edited her diary several times.
  • Pull your punches and stop nudging the reader. Susan Orlean15:11
    • Plainer writing is more confident and less "look at me." Then a really punchy line hits when it comes.
    • David Sedaris52:36 says his first books nudge readers in the ribs, asking "do you get it?" He learned to trust that people who aren't laughing are still listening.
    • Orlean calls overwriting a classic young writer error and says it is exhausting to read.
  • Switch off the tools that smooth you into the average. The Cultural Tutor1:03:14
    • Draft without worrying about spelling, syntax or grammar.
    • Nat Eliason15:15 wrote some chapters of Crypto Confidential as fragments, with no dialogue tags or scene setting, to make readers feel the mania. A tool would flag it as bad writing, but it did its job.
    • The Cultural Tutor pasted Edmund Spenser into Microsoft Word and it filled the verse with red lines. Carlyle capitalized surprising words, and a modern tool would flag every one.
    • Robert Macfarlane49:36 drops verbs on purpose, as in "Cliffs dropping near sheer to water." Grammarly dislikes it, which he takes as a badge of success.
  • Read the draft to someone who knows you outside work. Lulu Cheng Meservey53:01
    • This gets you out of "writer brain," where you perform, and into "friend brain," where your feet are up.
    • A spouse, parent or child will tell you it doesn't sound like you. A professional editor might only ask what should be said.
    • She has sent drafts to her husband and been embarrassed by how little they sounded like her.

2.6 Where writers disagree

Fiction can wear a mask; essays need you
FictionEssays, memoir, newsletters
Whose voiceA construction, a maskThe writer's own
ExampleKuang, Greer's LessFirst-person nonfiction
Style set byEach book (Gates of Fire)The writer's speech
Speech's roleRaw material for a personaStarting point, then denser
Most writers treat speech as a starting point, then tighten it, like Ezra Klein, who finds talk too loose for the page.

Some of this advice pulls in opposite directions, and the right call depends on your work.

  • Whether to write exactly as you talk. Ezra Klein36:40 says his spoken explanations of his book do not work on the page. Writing should be denser and less loose than conversation.
    • Most writers here use speech as a starting point, not the final text. Shaan Puri15:00 says it first and then writes it down, and Robert Greene30:29 cuts rhythms that come out awkward.
  • Whether the voice is you or a mask. R.F. Kuang27:40 says narrative voice should be detached from the author's personality, "a construction." Her Taipei novel's brash voice is not her own view.
    • Andrew Sean Greer13:15 gave Less a narrator much smarter and funnier than its hero. Steven Pressfield1:13:27 lets each book dictate its own style, such as the formal, archaic voice of Gates of Fire.
    • For fiction a mask can serve the story. For essays, memoir and newsletters, the writers above push toward the real person.
  • Whether to cultivate a voice at all. Steven Johnson1:23:05 built his by imitation. Paul Graham56:44 calls cultivating a personal style a gimmick, and Joy Harjo13:58 says it is already there.
    • The two fit together. Study others to learn moves, then write well and truthfully, and let the style be the part you can't help.
    • Harjo says her voice is the same whether she plays saxophone, speaks or sings. She says you get to what is unique by investigating your beliefs and where your mind obsesses.
  • How much of yourself to reveal. Garry Tan36:55 says sharing unpleasant experiences gave others permission to do the same.
    • But as a Stanford freshman he overshared in emails to a provost, who did not know what to do. He learned to match the amount to the person.
    • Neil Strauss7:13 asks for vulnerability with a conscience: where a toxic thought comes from, what it says about you, and what your relationship with it is. Raw diary entries are not enough.

Sources

Part of Clear Sentences and Voice in the growth library.