How to Write Powerful Stories — Brandon Stanton

How I Write 1h8 7 min #92
How to Write Powerful Stories — Brandon Stanton
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Summary

  • Brandon Stanton, creator of Humans of New York, built a following of 13 million and published five books by inventing a new genre of biography: photographing strangers on the streets of New York, interviewing them, and distilling their lives into short, powerful written stories paired with portraits. What started as a photography project evolved into a writing practice centered on drawing out deep, singular truths from ordinary people, and the conversation explores how he finds those stories, conducts interviews, and writes with a voice rooted in the oral tradition.

How Humans of New York evolved

  • It began as a plan to photograph 10,000 New Yorkers to recreate the city through portraits.
  • Early on, Stanton had brief conversations with subjects and transcribed short quotes.
  • Over time, the interviews became longer and more forensic, focused on uncovering deep themes and life arcs.
  • Writing and editing became central to the project, especially as the format expanded from single quotes to multi-part serialized stories on Instagram.
  • Stanton deliberately removed himself from the work, treating himself as a channel rather than a source, which he believed made the art better.

The interview as a craft

  • Stanton’s core skill is a specific type of interview: starting from zero with a stranger who knows nothing about him, often in awkward public settings like Fifth Avenue.
  • He creates an environment where nervous strangers open up and share their lived experience in a short amount of time.
  • Early in the project, he sought out colorful, visually distinctive characters; later, he took pride in photographing inconspicuous people and drawing profound stories from them.
  • He does zero preparation and relies entirely on curiosity and active listening, which he believes creates a level of presence people aren’t used to.

How truth emerges in an interview

  • Truth is often spoken haltingly, with pauses, as if being dug up from somewhere deep; it has gravity and is not floating on the surface.
  • Interviews rarely begin with truth; they begin with discomfort, clichés, generalities, and nervous laughter.
  • People initially present a persona, the “business card version” of themselves, the story they’ve crafted to move through the world.
  • With sustained attention, follow-up questions, and genuine interest, the interview moves below the persona to a place where answers come more slowly and the person is thinking through things for the first time.
  • Stanton describes this as pulling on a very long string “one spoonful at a time,” approaching a person’s life from different angles, characters, seasons, and arcs until he finds an illustrative moment to dig into.

Finding the story

  • Stanton follows the heat: he listens intently and leans in when something surprises or hooks him, using his own curiosity as a proxy for the audience.
  • He looks for a person’s struggle, because struggle provides plot (what they’re pushed against), transformation (they can’t battle something without being changed by it), and wisdom (the thing they’ve thought about most is their genius).
  • The best interviews reach a place of singularity, where the person is telling him something he hasn’t heard from anyone else in 10,000 interviews.
  • Singularity operates at two level: the events of a person’s life and the unique voice or way they turn a phrase.
  • When story and voice come together, as with a woman named Tanqueray, a former burlesque dancer whose distinctive voice led Stanton to spend months on a 33-part Instagram series, it is “absolute magic.”

The role of the editor

  • Stanton sees himself as an editor: from a 20-page transcript, he identifies the one moment that reveals something deeper about the person.
  • He writes the story with the questions themselves, noticing patterns in interviews and learning to ask for exactly what the story needs, descriptive details, emotional turning points, contradictions that need explaining.
  • Good writing, like good interviewing, requires pushing past the cliché and the surface to reach something earned and singular.
  • He challenges contradictions in interviews, asking people to explain when their stories don’t match up, which can lead to a new synthesis with deeper resonance than the initial version.

Unlocking hidden parts of people

  • People carry stories about themselves that serve their mental health and self-image, arranging memories to support a narrative that they are good and living correctly.
  • These stories are not always the truth; they are a truth, but not the only one.
  • The editing and interviewing process is a tool for getting into the locked parts of people’s minds, the trap doors and Pandora’s Box chambers that trauma or self-denial has closed off.
  • Many people, especially selfless ones like mothers who live entirely for others, close the door to their own heroism and accomplishments; unpacking their lives into a visible story arc allows them to see their own pride and distance.

Presence, intensity, and energy

  • Stanton’s energy in interviews is intense; he takes every person “deadly seriously” and will call out contradictions.
  • He modulates between masculine and feminine energy depending on who he’s talking to, switching tone between, say, young men on a street corner and an elderly woman in Jackson Heights.
  • This ability to move between energies has allowed him to work in every neighborhood in New York City and in war zones around the world.
  • He tells interviewees upfront that they don’t have to answer anything they don’t want to, and almost no one exercises that option, suggesting that when someone is fully present and motivated to understand you, there is an internal force that helps you open up.

Escaping the algorithm

  • Social media algorithms reward certain formats, currently favoring longer engagement time over short poetic quotes.
  • Writing the book Dear New York freed Stanton from the algorithm’s constraints; 75% of the stories in it were never posted online.
  • The book allowed for shorter, more nuanced, poetic quotes that wouldn’t perform well on social media.
  • Short quotes have a two-way quality: the reader brings their own interpretation, which may be less accurate but more meaningful than a fully explained idea.

The oral tradition in Stanton’s writing

  • All of Stanton’s stories come to him through voice, and his writing maintains the rhythm and cadence of spoken word.
  • Spoken word has less ornamentation than written word; it is more stilted, jumps around, and uses more repetition.
  • This gives Humans of New York stories the feeling of being spoken for the first time rather than polished in a room.
  • His writing style uses lists and repetition to build rhythm, as in a passage about New York where he stacks vivid examples, “the same narrow sidewalks, the same one-way streets, the same subway cars,” to create a cumulative, almost musical effect.
  • Even his 12,000-word first-person prologue for Dear New York was crafted to have the same texture and fabric as the interview-based stories.

Discipline and the creative process

  • Stanton flunked out of school and was undisciplined for the first 20 years of his life, skating by on natural ability.
  • He transformed his life by committing to reading 100 pages a day, which he did for several years, starting with nonfiction and biographies, then later reading 150–200 works of fiction to become a better writer.
  • He rooted his identity not in talent but in the amount of work he does each day, which he sees as the one thing that is democratically available to everyone regardless of genetics or privilege.
  • This discipline carried into Humans of New York: four interviews a day, every day, for years without missing a day.
  • His prologue for Dear New York went through 180 drafts; he iterates relentlessly rather than relying on bolts of inspiration.
  • Reading fiction taught him that anything is allowed if you do it well, freeing him from rigid rules about what constitutes quality writing.
  • He warns against art school and MFAs creating a rigid definition of quality that leads away from singularity, experimentation, and innovation.

Lessons from Robert Caro and Aaron Sorkin

  • Robert Caro, who is writing a 5,000-page biography of Lyndon B. Johnson, inspired Stanton with his ability to imbue a real person’s life with literary form that feels like fiction.
  • Short-form writing is excellent training because it teaches you what a story cannot do without, the essential bones of storytelling, which you can then build flesh around in longer formats.
  • Aaron Sorkin taught him that every story needs a plot, a clothespin on which to hang all the things you love about writing: exposition, character building, poeticism, wisdom.
  • A plot requires a character who knows what they want, has a goal and needs that can be fulfilled or disappointed, creating forward momentum that carries the reader.
  • The desire doesn’t have to be grand; it can be as simple as wanting your son to enjoy dinner tonight or getting sober, which is probably the most common story on Humans of New York because addiction is the struggle people face most.

Empathy as the foundation of storytelling

  • Stanton’s version of empathy is not “I am like this person” but rather “if I had been born in their shoes and walked their path, I might be a lot like them.”
  • Understanding what it’s like to be behind someone’s eyes and where they came from allows you to see how their environment shaped their personality.
  • This perspective overturns stereotypes: after living in New York, Stanton encountered so many surprises that he came to see that anyone could be a saint or a villain depending on circumstances, and that he himself had been both in the lives of others.

Stanton’s best writing advice

  • Root your creative identity in the process of showing up every day, not in external validation like followers, money, or awards.
  • If you write for an hour a day, you are a writer; if you’ve won Pulitzer Prizes but haven’t written in a year, a 16-year-old journaling is more of a writer than you.
  • The only thing you can fully control is whether you do the work, and that is the only reliable foundation for a creative life because the journey involves too much doubt and insecurity to be sustained by anything else.
  • Judge yourself by showing up: “I can take one more step today,” repeated all the way to the top of very tall mountains.
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