Dear New York

The 12,000-word prologue took 180 drafts, not a burst of inspiration. Stanton rewrote the first-person prologue of Dear New York 180 times. Its many threads spread out from a baby and weave back together in the final scene, and keeping it of one piece took that much iteration.

He says he is not someone who gets a bolt of inspiration and writes it out. The same habit shows elsewhere: he read 100 pages a day for years, then did four interviews a day for years without missing one. "The one thing that you can be proud of without ego is the amount of work that you do."

How I Write▶ 45:54

Write for the ear so new prose matches spoken stories. Every story in the book was told to Stanton aloud, so he wrote the prologue with the rhythm and cadence of speech so it would share the texture of the 500 interview stories around it.

Spoken word has less ornament, more repetition and more jumping around, which makes it feel said for the first time. David Perell says the rhythm of the opening paragraph, a list of every culture, religion and viewpoint, pulled him into the Grand Central exhibition.

How I Write▶ 50:43

Build a place from a rolling list of concrete details. The prologue bounces between about 30 people on the seven train, building "this summation of the city through its individual parts" in short, vivid beats that gather momentum.

Perell notes the technique works for any city: keep adding flash points like sidewalks, one-way streets and subway cars. Stanton could do it because he had stopped 10,000 strangers over 15 years, which he sees as the one thing only he has done.

How I Write▶ 51:50

A book let Stanton publish forms social feeds no longer reward. Algorithms stopped distributing very short, poetic quotes, so Dear New York became the home for shorter, more nuanced lines that need no justification. 75% of its stories were never posted online.

He largely stepped away from posting for two or three years to write it. "The book freed me from the algorithm."

How I Write▶ 34:27