Chapter 19 of 20 · Characters and Storytelling
1 The bottom line
Build the piece around one person with a struggle, a question and a five-second moment of change, and let facts arrive through them. Readers forget facts but remember people and the emotion attached to them.
2 Key takeaways
- Build the piece around one person, not a topic or a group. Readers remember facts because of the emotion attached to them.
David Gelb38:06 did not explain how to make egg sushi. He showed an apprentice who needed 200 tries and wept when the master approved.
- Find the person's struggle or central complication first. The struggle gives you a plot, a change and the person's hardest-won wisdom.
Wright Thompson14:19 built his Tiger Woods piece on Nike handing an extreme introvert a marketing plan made for the extrovert Michael Jordan.
- Build everything toward one moment where the person changes. If you cannot name that moment, you do not yet have a story.
Shaan Puri27:21 says the ending should be the opposite of the opening, like Scrooge hating then loving Christmas.
- Keep information in service of the story, and skim what the reader does not need to feel. Long explanation breaks the pull of the narrative.
Mitch Albom's36:03 mother praised his books for lacking long pages on how submarine widgets fit together.
- Find the story first, then draw the lesson from it. A lesson hunted for a story feels forced.
Morgan Housel24:44 stood out at The Motley Fool by telling stories about finance among thousands of writers publishing numbers and charts.
if you can find somebody's struggle, you will find a plot.
Brandon Stanton, Humans of New York
2.1 Choose who the story is about
Pick one person the reader can follow, and let the facts come through them.
- Tell the story of one person, not a group.
Morgan Housel21:05 says readers can see themselves in one person.
- When you write about groups, it becomes "them" and invites apathy.
- His best hook is letting readers feel they are looking in a mirror, as with the Vanderbilts.
David Gelb38:06 planned Jiro Dreams of Sushi around how different chefs make sushi. Test shorts showed him the people were the interesting part.
Gelb38:06 says Chef's Table teaches almost nothing about cooking, yet it has lasted because it follows a character's journey.
- Find a donkey to pull the reader through complicated material.
Patrick Radden Keefe59:38 borrowed the idea from Lawrence Wright.
- Ask who is going to pull the reader through all this material.
- It need not be one character. The reader only has to feel they are following someone.
- If no one else fits, be the donkey.
Michael Pollan24:30 says finding the way to put himself in the story is finding the story. - Pollan bought steer 534 for 600 dollars. That changed how feedlot staff talked to him and gave him decisions to write about, like the 15 dollar hormone implant
Pollan24:30.
- Choose characters who speak vividly and play against type.
Michael Pollan1:02:04 checks interview quotes for who sings and who is halting and boring.
- He wants someone with real authority who says it in a vivid way.
- Pollan likes people who break the stereotype, like a rancher who looks like a bookkeeper in a visor. He points to the little guys who beat the system in Michael Lewis's Moneyball and The Big Short.
- Tell a big event through someone standing away from the action.
Mitch Albom31:00 says pieces readers remember often sit away from the main action.
- After the Kennedy assassination, columnists wrote grand sentences about America. Jimmy Breslin went to the man digging the grave.
- At the Barcelona Olympics, Albom skipped the expected Carl Lewis story. He filed on a runner whose father carried him across the line after a torn hamstring
Albom50:15. - The father had taught his son to run by putting the boy's feet on his own. Almost nobody in America knew the runner, yet the column became one of Albom's best known
Albom50:15.
2.2 Find the struggle and the question
A struggle or a conflict gives the reader something to wait on.
- Look for what the person overcame before you decide how to tell it.
Brandon Stanton20:07 says a struggle gives you three things at once.
- It gives you a plot, because the person pushed against something.
- It gives you transformation, because no one chews on a problem for years without changing. It gives you wisdom, because the struggle is what they have thought about most.
- The most common long story hears is someone getting sober, because addiction is the thing people struggle with most.
- Name the central complication of the person's life and how they handle it daily.
Wright Thompson14:19 repeats Gary Smith's definition of a profile.
- Show how they try to solve it day to day. Most of that happens inside them.
- Keep the person as complex in their decisions as you are in yours.
- Ask what the experts in a field fight about.
Michael Pollan1:00:37 says that if there is no conflict, there is no tension.
- opens A World Appears with a bet between neuroscientists Christof Koch and David Chalmers. The bet was over whether the neural correlates of consciousness would be found in 25 years.
- A simple bet sets up tension that carries readers for 20 pages.
- David Perell asked the same question of a beekeeping conference.
- Dig for the origin story that explains why the person does what they do.
David Gelb7:49 says the how is not enough. The why is the mystery of each episode.
- He peels back layers to find the moments the subject got it wrong and what they learned.
- Once the audience understands the motivation, the mannerisms and craft start to matter more. Spider-Man's origin explains the whole character: he lets a burglar go, then loses his uncle.
2.3 Build toward the moment of change
Shape the story so it builds to one turn, and show what led to it.
- Name the five-second moment of change.
Shaan Puri27:21 takes this from Matthew Dicks' Storyworthy: everything builds to the one moment the character transforms.
- Check the ending. It should be the opposite of the opening, as in every rom-com.
- The turn usually comes after the character loses it all and is cornered into bravery
Perell's roundup of Puri30:20. The player settles down. The workaholic lawyer opens a bakery. - In Puri's Batman example, the character is told the only way out of the cave is to jump without the rope, and he leaps.
- Fill the middle with what triggered the turnaround and what you tried.
Shaan Puri38:36 says most origin stories jump from "I got laid off" to "then everything was great."
- Show what made you decide to change, the first thing you did, and the resistance you overcame.
- Puri cites the Pixar idea that audiences love the hero for how hard they try, not for winning. An instant success is a weak story.
- He told David his version had an arbitrary epiphany and fast-forwarded the montage.
- Write the past as not yet decided.
Dan Wang55:41 says every event feels impossible before it happens and obvious afterward.
- Put the reader inside the uncertainty of the time.
Jimmy Soni59:59 cites David McCullough: put the reader in the perspective of people who did not know how history would turn out.- Franz Ferdinand's driver took a wrong turn toward the assassin, and nobody expected the Soviet collapse.
- The Brooklyn Bridge looks inevitable now, but nobody then knew if it could be built.
Soni59:59 stayed riveted by A Night to Remember even though everyone knows how the Titanic ends.
- Look for the small human act inside the big story.
David Grann1:16:56 says size is irrelevant and meaning is what counts.
- He prefers telling big events from the bottom up, through ordinary people with their own desires and debts.
- In The Wager, the captain and gunner shook hands before the captain was left on the island. Then they went back to hating each other.
2.4 Fit the information inside the story
Keep only the facts that move the person forward, and keep them out of the way.
- Tell the slow parts fast and the fast parts slow.
Mitch Albom36:03 learned this at the family dinner table.
- His aunts got stuck on details like whether it was 1945 or 1946. His uncles told war stories that moved.
- Skim the explanatory stretches and linger on the moments that matter.
- Give each event a specific detail that earns its place.
John Lennox's32:28 editor warned him that an episodic autobiography has length but no depth.
- Keep an event only if something specific happened there that makes it interesting. Move the rest out.
- Listing Veritas Forum talks in Austin on Tuesday and Denver on Wednesday is boring without particular moments.
- Skim past research and tell it through your own experience.
Paul Millerd55:10 did not spend three or four pages on the method and findings of the ideal-self and ought-to-self study.
- He told it through his own experience of leaning on the ought-to self, then kept moving. He did not want to linger on the study.
- The book has over 200 references, and the nerdy quotes alternate with personal reflection.
Ana Lorena Fabrega20:46 leaned on research by instinct. David pushed her to write stories from her classroom, because people remember stories, not facts and figures.
- Anchor data in a concrete scene, and keep statistics out of the middle of a personal story.
Peter Attia4:28 says even a book full of data needs a story to anchor the reader.
- Attia opened Outlive with the first patient he saw die, a case of fast death, to contrast with the slow death medicine handles badly.
Rob Henderson55:38 followed Tara Westover's warning that dropping data into a personal narrative will break the spell. He kept the early chapters in story and put the research in a preface and the last few chapters.- Many readers skip prefaces, so Henderson's preface was a compromise to reassure readers there was a point. His editors wanted statistics in chapter one
Henderson55:38.
2.5 Decide what it means and close
Choose the meaning of the story, state the lesson, and pull the reader on.
- Find the story, then ask what broader lesson it carries.
Morgan Housel24:44 says he has never started with a lesson and then hunted for a story to fit it.
- His books follow this shape. Each chapter is a story, then the takeaway.
Ryan Holiday1:06:27 wants stories that are a theme, not an aberration, so he can stack similar ones to show an observable trend.
- Decide what the facts mean, because the facts cannot change.
Tucker Max43:51 says in a memoir you choose the story you tell about events you cannot alter.
- His parents neglected him. He now tells it as hardship that also made him independent and a critical thinker.
- It took years of therapy and writing to reach this version. It is sad and also inspiring.
- End each short story with a lesson and a bridge to the next.
Ali Abdaal34:30 loves The Psychology of Money for this.
- Each chapter has an engaging story, a timeless lesson, and a final line that makes you want to turn the page.
- The book has 20 chapters of about 1,500 to 2,500 words each. The story keeps you reading and the lesson gives the payoff.
- Tell the reader, subtly, why the story is worth their time.
Susan Orlean6:29 contrasts bullet points with saying "sit back and let me tell you this amazing story."
- A story needs mood, characters and a subtle explanation of why it matters.
- She imagines telling a dinner guest about the biggest library fire in American history, a topic they might not expect to care about.
2.6 Where writers disagree
Writers differ on how famous the subject should be, how much to bend the facts, and how faithful a portrait must be.
- Familiar subjects versus unknown ones.
Ryan Holiday1:06:27 likes stories about people the reader already has an opinion about, and finds very obscure subjects lack the power his lessons need.
Mitch Albom50:15 went the other way. His most remembered column was about a runner almost nobody in America knew, because the father and son theme was one everyone relates to.
Brandon Stanton20:07 builds whole stories on strangers, because their struggle supplies the plot.
- How closely the story must match what happened.
Yann Martel1:01:37 says you do not want lies, but facts only go so far.
Marc Andreessen36:51 would change the names, dates and events but keep everything that happened, so he can use 30 years of tech experience without writing a tell-all.- He has not written the book yet. He compares the idea to the show Ray Donovan, whose fixer cases reportedly all happened
Andreessen36:51.
- How faithful a portrait must be to its subject.
Patrick Radden Keefe8:10 tells subjects the piece will look like a painting of them, filtered through his sensibility, even in a friendly profile.
- He says capturing someone's self-image is the job of a PR person. His goal is a picture recognizable to people who know the person and resonant to people who do not.
Tucker Max43:51 shows the other side of this. The meaning of your own story is yours to decide, even when the facts are fixed.
Sources
- Harvard Professor Teaches Writing (Michael Pollan Interview) ·
How I Write - How to Become a Novelist Without Writing Lessons (Yann Martel Interview) ·
How I Write - The Secret to Great Stories (David Gelb Interview) ·
How I Write - New Yorker Writer Teaches the Craft of Writing (Patrick Radden Keefe Interview) ·
How I Write - How to Write Incredible Stories (Wright Thompson Interview) ·
How I Write - I Interviewed 40 Writers in 2025 (Here's What I Learned) ·
How I Write - How to Write Powerful Stories — Brandon Stanton ·
How I Write - Meet The Writer Behind Killers of the Flower Moon ·
How I Write - Award-Winning Author Reveals Her Writing Process (Susan Orlean Interview) ·
How I Write - Why Selfish Writing Is Better Writing (Morgan Housel Interview) ·
How I Write - How to Write Exceptionally Well (Mitch Albom Interview) ·
How I Write - Why You Should Write Less Often (Dan Wang Interview) ·
How I Write - Oxford Professor: AI Is Humanity's Attempt to Make God (John Lennox Interview) ·
How I Write - 171 Years of Writing Knowledge in 90 Minutes ·
How I Write - The Secret To A New York Times Best Seller – Tucker Max ·
How I Write - Meet the Stanford Surgeon Turned Podcaster — Peter Attia ·
How I Write - Cambridge PhD: How to Write a Memoir — Rob Henderson ·
How I Write - The Simple Steps to Fuel Your Creativity – Ryan Holiday ·
How I Write - What’s Wrong with Writing Education? — Ana Lorena Fabrega ·
How I Write - Leaving McKinsey to Write Full-Time | Paul Millerd | How I Write Podcast ·
How I Write - How to Tell an Unforgettable Story (The Shaan Puri Interview) ·
How I Write - The Writing Secrets of a World Class YouTuber – Ali Abdaal ·
How I Write - How to Write Insanely Well (Morgan Housel Interview) ·
How I Write - Marc Andreessen: Blogposts, Tweetstorms, and Manifestos ·
How I Write - Derek Sivers: No Wasted Words ·
How I Write - How to Write Like An Athlete | with Jimmy Soni | How I Write Podcast ·
How I Write
Part of Characters and Storytelling in the growth library.