Chapter 20 of 20 · Revising, Habits and Readers
1 The bottom line
Picture one real reader, with a face, and write to that person. A specific reader decides your tone, what to explain and what to cut, while writing for everyone reaches no one.
2 Key takeaways
- Write to one person, not to a crowd. A crowd has no face, so you cannot tell what it needs.
- One writer finds his best work in a daily 200 to 250 word journal sent to one friend, which takes about an hour and a half
Packy McCormick1:05:04. - Ali Abdaal typed an answer to a med school friend about investing. The video made from it has about 8 million views and over $100,000 in revenue
Ali Abdaal13:46.
- One writer finds his best work in a daily 200 to 250 word journal sent to one friend, which takes about an hour and a half
- Choose a reader you can actually know. You cannot know the market, but you can know yourself and your friends.
- A book on the tables now was conceived 4 or 5 years ago, so a chased trend is already old
Matt Haig25:05. - Atul Gawande imagines readers like himself and his friends, and says it surprised him how well the books did
Atul Gawande56:45.
- A book on the tables now was conceived 4 or 5 years ago, so a chased trend is already old
- Aim slightly above what the reader knows, and add what they lack. Smart readers are bored by recaps and by over-explaining.
- Fareed Zakaria assumes readers know what happened and supplies the framework, context or history they have not thought of
Fareed Zakaria12:41. - Kevin Kelly says if you mention DNA you do not need to explain it, unlike newspaper tech writers trained to target an 11th grader
Kevin Kelly10:25.
- Fareed Zakaria assumes readers know what happened and supplies the framework, context or history they have not thought of
- Match tone, references and form to that reader. A reference or joke that needs background the reader lacks falls flat.
- Robert Mac's Road Runner joke gets a laugh every time but got zero from Indian businessmen at a fundraiser for a Maryland candidate
Robert Mac12:58. - In St. Ives, the cafe with a five pound sign had a queue while the cafe with the huge menu was empty
Harry Dry22:50.
- Robert Mac's Road Runner joke gets a laugh every time but got zero from Indian businessmen at a fundraiser for a Maryland candidate
- Tell the reader what they get before you start. They pay with time and attention, and nobody cares about your excitement.
- A book costs a reader about $25 and nine hours, so Daniel Pink asks what promise he is making
Daniel Pink49:31. - Lulu Cheng Meservey's examples of self-focus are crypto firms bragging about the blockchain and AI products bragging about being built on AI
Lulu Cheng Meservey1:00:39.
- A book costs a reader about $25 and nine hours, so Daniel Pink asks what promise he is making
when you try to write for the stadium, you don't hit the stadium.
Packy McCormick, Not Boring
2.1 Pick the reader before you write
A narrow, named reader forces sharp choices, and "everybody" forces none.
- Name your audience precisely. Writers talk themselves into believing everybody will read the book, and
Daniel Pink18:48 says it is never everybody.
- Pink says a proposal must clearly articulate who the audience is, because naming them forces sharper choices about what the book contains.
- Go down to what the reader is doing when they see your words
Harry Dry22:50. - A tourist walking past a cafe needs "coffee and pastry equals 5 lbs", not a huge menu of croissants
Harry Dry22:50. - Snapchat spent 7 million pounds on a Super Bowl ad aimed at an average viewer age of 39, because they did not think about who they were talking to
Harry Dry22:50.
- Give up on pleasing everyone. Trying to please everyone satisfies no one.
- Billions stampede for the exits, but a dozen come down from the cheap seats to the front row. Write for them
Paul Harding1:00:28. - Going broad to please everyone is a common mistake, and the result is liked by almost nobody
Neil Strauss1:06:11. - Perell's podcast is deliberately too geeky about craft for most listeners and adored by the few who want it
Jerry Seinfeld39:53. - Online you compete with every writer in the world. Neil Cybart owns a smaller pond by writing about Apple every day
Ben Thompson1:25:41.
- Billions stampede for the exits, but a dozen come down from the cheap seats to the front row. Write for them
- Decide whether you are writing for art or for a wide readership. Neither is wrong, but being unclear about which one you are hurts
David Shelley26:45.
- Pick your aim honestly before you start, because it decides how you should write.
- Ronald Firbank privately printed experimental novels in the 1920s knowing there was no market. James Patterson wants the widest number of people to enjoy storytelling.
- Say who you are not writing for. Naming the reader frees you to write with force
Paul Millerd11:28.
- After a scathing email, Millerd began a defensive reply, saw it was a letter to himself, and turned it into a post for unconventional weirdos, not people thriving on the default path.
- In the next two years his curiosity conversations went from one a month to a couple a week.
2.2 Start with yourself, then bridge to them
You are the one reader you know, so begin there and then make the piece usable for others.
- Write what you would want to read. Your own interest is a real signal.
- You are the only reader you will ever know, so be honest about the book you want to read and hope it matches what others want
Matt Haig26:21. - Tim Urban makes what he would most want someone to send him. If he is bored, confused or finds something bad, he changes it
Tim Urban1:10:24. - The Cultural Tutor wrote a thread on why we wear ties because he was sitting there wearing one and wanted to know
The Cultural Tutor1:01:17. - Chamath Palihapitiya writes his annual letter for himself, since he is the only guaranteed rereader. That gives it a clear point, though most readers finish only 10 to 20%
Chamath Palihapitiya4:27.
- You are the only reader you will ever know, so be honest about the book you want to read and hope it matches what others want
- Then shape the draft so others can use it. A first draft for yourself is not yet for the reader.
- Ryan of AJR thinks only about his own feeling in the first draft, then crafts it so people will not dismiss it as a narcissistic exercise
Jack and Ryan of AJR1:18:30. - Ask how what you want to say might fit into somebody else's life. Boring talkers stop asking
Alain de Botton1:10:49. - A friend told de Botton he was writing a book his academic father and his rural Swiss nanny could both enjoy
Alain de Botton1:10:49. - Counterpoint: guessing only what people like makes a boring artist, and "I make art only for myself" can be dangerous
Jack and Ryan of AJR1:18:30.
- Ryan of AJR thinks only about his own feeling in the first draft, then crafts it so people will not dismiss it as a narcissistic exercise
- If your idea is far from their interests, build a bridge. You cannot change what people already care about.
- Bold ideas are fine, but they need a receptor to attach to. Build a bridge, like an API, between where you are and where they are
Lulu Cheng Meservey24:14. - Treat the message as medicine and choose the candy coating. Then show up where that audience gets its information
Lulu Cheng Meservey26:00. - A writing show framed around AI works because everyone already asks how to use AI for writing. Stripe went after developers on Hacker News
Lulu Cheng Meservey26:00. - Kamala Harris told national defense voters that recruits need a 10th grade reading level for the army field manual, so education feeds the army
Lulu Cheng Meservey24:14.
- Bold ideas are fine, but they need a receptor to attach to. Build a bridge, like an API, between where you are and where they are
2.3 Put a face on the reader
A named person in your head keeps you out of performance and lets you hear how the words land.
- Picture a real person with a face. A faceless audience pulls you into stiff teacher voice.
- Brie Wolfson imagines a real person across the table, often Stewart Brand, and asks whether he would get a twinkle in his eye or go to sleep
Brie Wolfson33:50. - Writing to an abstract audience tends to produce teacher voice. Ask what question you are answering and what you are helping the reader see
Brie Wolfson37:50. - Friends who are brilliant speakers send her timid, fact-heavy writing with no humanity until they picture a person
Brie Wolfson33:50. - Rilke's Letters to a Young Poet and Stegner's Angle of Repose show how intimate writing to one person can be
Brie Wolfson37:50.
- Brie Wolfson imagines a real person across the table, often Stewart Brand, and asks whether he would get a twinkle in his eye or go to sleep
- Write the draft as a message to a friend. It loosens the performance.
- Perell challenged Steph Smith to write her next piece as a private email to him and decide later whether to publish
Steph Smith46:25. - Tim Ferriss scrapped his draft of The 4-Hour Workweek, opened a Gmail compose window, and wrote the first tens of thousands of words as if emailing a friend
Ali Abdaal17:56. - Abdaal's investing explanation for his friend was 90% done before it became a video
Ali Abdaal13:46. - Letters from the 17th to 19th centuries have lasted because they lack performativeness
Steph Smith46:25. - Sahil Bloom began a monthly email to about ten family and friends, sent it for more than five years, and it grew to about 2,000 readers
Sahil Bloom2:35.
- Perell challenged Steph Smith to write her next piece as a private email to him and decide later whether to publish
- Pick a reader who changes how you write. The right imagined person acts as an editor or removes fear.
- Tyler Cowen thinks "Alex is going to read that", so he makes the text simpler and clearer
Tyler Cowen and Alex Tabarrok10:47. - Scott Galloway writes as if his sons at 40 are the only audience, which removes the fear of strangers' approval
Scott Galloway17:51. - When Tim Urban drifts into writing for the snootiest critic, he remembers the friends in his head who read him on Twitter
Tim Urban15:35. - Urban caught himself explaining a concept for his book, wrote it as a tweet to subscribers, and found the tweet version better
Tim Urban15:35. - Marcus Aurelius wrote Meditations privately, addressing himself as "you". It has lasted 2,000 years
Ryan Holiday36:36.
- Tyler Cowen thinks "Alex is going to read that", so he makes the text simpler and clearer
- Picture one distracted reader in one moment. Real readers are half-attentive.
- Readers scroll on the bus or while waiting for a late friend, brain half on. Understand your own state in that setting and write for the person in it
Shaan Puri47:15. - 119,000 impressions are 119,000 individual people in 119,000 separate moments
Shaan Puri47:15.
- Readers scroll on the bus or while waiting for a late friend, brain half on. Understand your own state in that setting and write for the person in it
2.4 Decide what the reader needs from you
The reader spends time and attention, so decide what they get in return before you write.
- Name the promise you are making. Pink asks this before any project
Daniel Pink49:31.
- A reader spends about $25 and nine hours, so he wants them to finish feeling the time was well spent. A nonfiction writer should be useful, so readers do different things and not only think differently.
- He applies the same promise to his plays, hoping audiences approach their kids and co-workers a little differently.
- Name the job the reader hires you for. People read because they have a job they want done

Lenny Rachitsky1:11:03.
- Pick the job, such as getting better at a career, learning to make money or being entertained, then do it better than anything else. Treat reader questions as a puzzle board to fill in one by one.
- Newsletters that just pontificate on ideas face a far higher bar than ones that solve a specific job.
- Define where the reader is and where you want them. You cannot start a race in the middle
Harry Dry21:41.
- Treat the reader's current attitude as point A and the desired attitude as point B, like two telephone poles. Your job is to string the wire.
- Meservey's planning doc has four headings: the business objective, who must take what action, what they must believe, and where they already spend their attention
Lulu Cheng Meservey1:00:39.
- Lead with what the reader gets, not your excitement. Nobody cares about your passion, only how it improves their life
Lulu Cheng Meservey1:00:39.
- Put your commercial interest aside and ask what you could say that makes the audience feel understood. Link back to the company later
Lulu Cheng Meservey55:14. - Keep the reader's problem and benefit at the center of an announcement. Lines like "I've always wanted to do this and I'm excited to announce" forget to say why it matters to them
Lulu Cheng Meservey1:08:06. - Readers use your honest reflections to see themselves. If you posture to look good, they get almost no insight
Tucker Max42:08. - Apple's old think different era made people feel understood, unlike ads that push features Apple wants used
Lulu Cheng Meservey55:14.
- Put your commercial interest aside and ask what you could say that makes the audience feel understood. Link back to the company later
2.5 Set the level, tone and references
Know what the reader already knows, then pitch every explanation, joke and reference at that distance.
- Assume the reader is smart and aim a little above them. Most readers are not slow, and recaps waste their time.
- Kelly told Wired writers they were writing to him and had to amaze him. Explain enough, but not everything
Kevin Kelly10:25. - Pinker writes for people who are intellectually curious and have some education. His editor and friends in other fields stand in for that reader
Steven Pinker5:47. - Johnny Harris says "I know you're smart, you can get this, but you may not know about this, let me show you". Readers who pretend to know a reference stop being curious
Johnny Harris56:35. - He contrasts this with journalists who use jargon to impress peers instead of the audience
Johnny Harris56:35.
- Kelly told Wired writers they were writing to him and had to amaze him. Explain enough, but not everything
- Test the draft on a stand-in reader. Someone who gets bored or confused shows you what to fix.
- Johann Hari tells his story aloud to a 12-year-old and records it. A 12-year-old can follow almost anything but gets bored fast, so you see what to cut
Johann Hari25:42. - Dana Gioia pictures a bright teenager who knows little, a fellow writer who knows too much, and someone in between. He asks what could interest all three
Dana Gioia15:06. - Hari can tell the story of Chino, the former crack dealer, in 15 minutes this way
Johann Hari25:42. - Gioia will spend a whole day on one paragraph testing which examples to include
Dana Gioia15:06.
- Johann Hari tells his story aloud to a 12-year-old and records it. A 12-year-old can follow almost anything but gets bored fast, so you see what to cut
- Say the reader's doubt out loud. It builds trust and shows you are paying attention to them.
- Shaan Puri imagines what the reader is thinking at that point and says it, such as "I know what you're thinking, but you're wrong"
Shaan Puri1:08:36. - Jon Collins writes BibleProject scripts as a dialogue with Tim Mackie, using the questions he really had while learning. The beginner voices the doubt the viewer is too embarrassed to say
Tim Mackie and Jon Collins1:06:06. - Susan Orlean does not collect orchids and does not even like Florida, yet wrote The Orchid Thief by going through the discovery first as the reader's proxy
Susan Orlean14:02.
- Shaan Puri imagines what the reader is thinking at that point and says it, such as "I know what you're thinking, but you're wrong"
- Check every reference, joke and form against what this reader knows. A mismatch kills it.
- Rule number one is know your audience: who they are, what they grew up with and what patterns they think in
Robert Mac12:58. - Pitch each joke at the right distance. Too near impresses no one, and too far kills the horse
Andrew Hunter Murray46:25. - Even your pitch should carry the tone. An irreverent comedy needs an irreverent outline
Noah Hawley31:07. - For kids, make characters older than your readers and match density to age
Tish Rabe12:05. - Hawley pitched a 70s Bill Murray style crime story by rambling about how he might segue into the pitch, and the executives felt the tone first
Noah Hawley31:07. - Rabe uses a line or less a page for toddlers and up to eight lines for older readers
Tish Rabe12:05. - Taylor Tomlinson studies what people see when she walks on stage. She says her round face and Midwestern daughter vibe decide which edgy jokes she can pull off
Taylor Tomlinson7:04.
- Rule number one is know your audience: who they are, what they grew up with and what patterns they think in
2.6 Revise from the reader's seat
Reread the draft as that reader and cut what they would skip, resent or not understand.
- Ask who is reading each word and how it will land. Johnny Harris calls empathy with the viewer his most important sensibility
Johnny Harris21:21.
- He wrestled over adding "husband to 40 wives" to a sentence about Joseph Smith. It is a familiar anti-Mormon trope, but he judged most of the audience would find it intriguing.
- Cut what bores them, even if it happened to you. Learn the difference between your interesting ideas and your merely lived ones
David Sedaris1:09:00.
- A 12 hour delay at O'Hare feels like the end of the world to you and is boring to everyone else.
- Remember what it is like to read. Patrick Radden Keefe asks whether he would enjoy getting the email he is sending
Patrick Radden Keefe1:04:44. - He gets pitches of 5,000 words for The New Yorker. An editor receives a hundred emails a day, so he says to do it in three tight paragraphs
Patrick Radden Keefe1:04:44.
- Cut the complaint and the self-regard. Keep your loyalty to the reader
Jonathan Franzen12:45.
- Trauma dumping is focused on the self and carries a flavor of complaint, which is incompatible with the bond he wants.
- In an apology, show you are at least as bothered as the reader, but do not overshoot or they will start comforting you
Lulu Cheng Meservey1:16:39. - A book full of complainers can still work if the reader is invited to laugh at them, as in Halle Butler's Banal Nightmare.
- Check the draft where the reader will see it. Layout changes how copy lands.
- Harry Dry writes his newsletter in ConvertKit and ads in Figma. He does not trust a Google Doc, where a line might spill to three lines once pasted
Harry Dry25:09. - Ogilvy advised testing a billboard against seven other ads around it, not alone in Photoshop
Harry Dry25:09.
- Harry Dry writes his newsletter in ConvertKit and ads in Figma. He does not trust a Google Doc, where a line might spill to three lines once pasted
2.7 What the books say
Before you write for one reader, the books say to work out where that reader stands on the problem, because that decides how you open.
- Find out whether your reader has already proposed or tried a solution.
Barbara Minto, The Minto Pyramid Principle
- Place the reader in one of seven positions, such as no solution, a solution they doubt, one they cannot implement, one that failed, or several options. Each position has its own standard Situation, Complication and Question.
- Get this wrong and both your introduction and your reasoning come out muddled.
- Start from what the reader has already done, and use it as the Complication.
Barbara Minto, The Minto Pyramid Principle
- In the book's example, Jackson Foods changed its terms of trade to raise order sizes. It made little difference, so the failed fix became the Complication.
2.8 Where writers disagree
| Ignore the market | Study the market | Middle path | |
|---|---|---|---|
| Who says it | Matt Haig | David Shelley | Dana Gioia |
| What you do | Write the book you want to read | Read the genre, bestseller lists, covers, reviews | Learn why readers come to a genre |
| Aim | Honest match with readers | Widest readership | Give the experience readers want |
| Example | Chasing trends is already late | Lee Child researched and picked his agent | Serve the genre's promise |
Writers split on whether to study the market, how many readers to hold in mind, and how wide to aim.
- Ignore the market, or study it. It depends on whether your goal is a wide readership.
- Haig says researching the market is how you fail to be commercial
Matt Haig25:05. - Shelley says a writer after the widest readership should read heavily in the genre, study bestseller lists and covers, and read reader reviews
David Shelley27:25. - Lee Child did a lot of research and chose his agent because the agent was good at launching big commercial authors
David Shelley27:25. - A middle path: learn why people come to a genre and what experience they want, then give it to them
Dana Gioia3:10:26.
- Haig says researching the market is how you fail to be commercial
- Follow your readers, or teach them to like your work. Audience signals help, but they can also steer you away from yourself.
- Ava Huang is informed by what resonates, but she also makes clear what is part of her work even if it is not the most popular
Ava Huang42:00. - If you only follow the audience, you end up making things other people like and you don't
Ava Huang42:00.
- Ava Huang is informed by what resonates, but she also makes clear what is part of her work even if it is not the most popular
- Hold one reader, or two or three. One reader gives intimacy, and several levels give reach.
- Packy McCormick says writing for one person is more likely to reach the stadium
Packy McCormick1:05:04. - Lee Child describes readership as rings of Saturn: habitual readers at the center and casual readers at the edge. His answer is a style experienced readers enjoy and casual readers can follow
Lee Child21:02. - Ryan Holiday argues the most specific writing can be the most universal
Ryan Holiday36:36.
- Packy McCormick says writing for one person is more likely to reach the stadium
- Hide the obscure reference, or drop it. A reference that needs background knowledge dies when the reader lacks it.
- Ted Gioia tucks an arcane allusion into a throwaway phrase so the surface stays plain, and the rare reader who gets it is delighted
Ted Gioia22:38. - He wrote that music awoke him from his dogmatic slumber, Kant's phrase about Hume, and figures one reader in a thousand catches it
Ted Gioia22:38.
- Ted Gioia tucks an arcane allusion into a throwaway phrase so the surface stays plain, and the rare reader who gets it is delighted
- Aim for reach, or for the few who matter. Small audiences can do real work.
- A 30-minute Loom that 45 people finish saved those 45 from a meeting
Sam Corcos1:09:07. - For email, appealing a little to a ton of people does not work. A small list that cares will forward your emails, and some writers prune their lists on purpose
Lulu Cheng Meservey42:45. - Applicants cite company podcasts that only about 100 people heard
Sam Corcos1:09:07.
- A 30-minute Loom that 45 people finish saved those 45 from a meeting
Sources
- How to Make Your Writing More Funny (Taylor Tomlinson Interview) ·
How I Write - This Is What a Harvard Writing Masterclass Feels Like (Francine Prose Interview) ·
How I Write - How to Write a Book Millions of People Read (Matt Haig Interview) ·
How I Write - The Secret Behind Decades of Daily Writing (David Sedaris Interview) ·
How I Write - Pixar's Secret Storytelling Formula (Andrew Stanton Interview) ·
How I Write - Learn How to Write Novels in 1 Hour (Andrew Hunter Murray Interview) ·
How I Write - Emmy Award-Winner Teaches Writing (Noah Hawley Interview) ·
How I Write - How to Write For Kids (Tish Rabe Interview) ·
How I Write - New Yorker Writer Teaches the Craft of Writing (Patrick Radden Keefe Interview) ·
How I Write - Watch This Before Publishing Your Book (Hachette CEO Interview) ·
How I Write - Master Comedian Breaks Down 13 Jokes — Robert Mac ·
How I Write - Oxford Professor Teaches the Craft of Writing (Diarmaid MacCulloch Interview) ·
How I Write - Learn to Write Page-Turners in 63 Minutes (Lee Child Interview) ·
How I Write - Learn to Write Persuasively in 70 Minutes (Fareed Zakaria Interview) ·
How I Write - How to Improve Your Writing Skills (Daniel Pink Interview) ·
How I Write - Why Serious Writers Need to Be Funny (Jonathan Franzen Interview) ·
How I Write - How to Use Writing to Improve Your Thinking — Atul Gawande ·
How I Write - Award-Winning Author Reveals Her Writing Process (Susan Orlean Interview) ·
How I Write - How to Create Original Ideas — Stefan Sagmeister ·
How I Write - AJR Reveal Their Songwriting Secrets ·
How I Write - How to Write Something Truly Beautiful (Alain de Botton Interview) ·
How I Write - How to Read the Bible (Tim Mackie and Jon Collins, The Bible Project) ·
How I Write - Pulitzer Winner Breaks Down the Art of Writing (Paul Harding Interview) ·
How I Write - Harvard Professor Explains The Rules of Writing (Steven Pinker Interview) ·
How I Write - This Research System Will Change How You Write — Johann Hari ·
How I Write - Meet Silicon Valley’s #1 PR Expert — Lulu Cheng Meservey ·
How I Write - The Ultimate Guide to Writing with AI ·
How I Write - Johnny Harris Reveals How He Writes YouTube Videos ·
How I Write - Writing Advice Every Writer Should Hear (Dana Gioia Interview) ·
How I Write - The Secret To A New York Times Best Seller – Tucker Max ·
How I Write - How He Started the Paid Newsletter Trend — Ben Thompson ·
How I Write - Learn Copywriting in 76 Minutes – Harry Dry ·
How I Write - NYU Professor: Writing Masterclass in 84 Minutes – Scott Galloway ·
How I Write - The Simple Steps to Fuel Your Creativity – Ryan Holiday ·
How I Write - Seinfeld’s Timeless Lessons on Creativity and Consistency ·
How I Write - How to Write Well (in a Distracting World) — Ted Gioia ·
How I Write - How Writing Helped This CEO Build a $300m+ Company | Sam Corcos ·
How I Write - Leaving McKinsey to Write Full-Time | Paul Millerd | How I Write Podcast ·
How I Write - How to Be Great? Just Be Good, Repeatably | Steph Smith | How I Write Podcast ·
How I Write - The Art of “Taste” — Brie Wolfson ·
How I Write - The FBI Called This Writer About Seduction Training — Neil Strauss ·
How I Write - How to Tell an Unforgettable Story (The Shaan Puri Interview) ·
How I Write - Packy McCormick: A Tactical Masterclass in Online Writing ·
How I Write - Tim Urban Breaks Down His Viral TED Talk ·
How I Write - Sahil Bloom’s Content Empire Playbook | How I Write Podcast ·
How I Write - The Writing Secrets of a World Class YouTuber – Ali Abdaal ·
How I Write - Write Like a Billionaire | Chamath Palihapitiya | How I Write Podcast ·
How I Write - How Lenny Rachitsky Got 531,000 Substack Subscribers | How I Write Podcast ·
How I Write - The Secret to Writing with Emotion, Without Oversharing — Ava Huang ·
How I Write - WIRED Founding Editor Answers My Writing Questions — Kevin Kelly ·
How I Write - Learn Marketing in 80 Minutes — Lulu Cheng Meservey ·
How I Write - The Cultural Tutor: From McDonald's to Twitter Stardom ·
How I Write - How to Teach Millions of People with Your Blog — Tyler Cowen & Alex Tabarrok ·
How I Write - The Minto Pyramid Principle: Logic in Writing, Thinking and Problem Solving · Books
Part of Revising, Habits and Readers in the growth library.