Wait But Why

Urban's voice came from years of blogging with no pressure to be good. Before Wait But Why, Tim Urban wrote about 300 posts over six years on a blog he used to procrastinate. He was not trying to be a writer, just having fun, the way he would send six friends a funny email about his day.

The blog broke every school-paper rule: no research, no format, a funny idea turned into about three paragraphs in 20 minutes. The 300 posts showed him some readers loved his voice, which gave him the confidence to keep it. "I wasn't trying to be a good writer."

How I Write▶ 1:53

Lists and stick-figure cartoons were discovered by trying things, not planned. Lists like 19 Things I Don't Understand and 25 Things That Annoy Me came out of the sandbox blog, and drawings only appeared near the end of its six years. Readers liked the cartoons right away, which told him he had a whole new thing.

He did not know if a basic Blogger site would even accept an uploaded image, and drawing on a tablet was new to him. He says he can't use the list format anymore because BuzzFeed made it trite.

How I Write▶ 1:53

Write for readers who are friends, not for the snootiest critic. While drafting his book, Urban explained an idea as a long tweet and found it better than the book version. When he feels unsure, his writing turns flat and matter-of-fact.

His fix is to ask how he would explain it to a friend if it were 2006 and he were just blogging, or as if he were having fun on Twitter. The pull toward critics is stronger with a book because the New York Times might review it.

How I Write

One chapter of a blog series outgrew the format and became a book. The Story of Us started as a post on why society is so tribal. Chapter 11 of 12, applying it to current politics, grew longer than the other 10 chapters combined, and a 100,000-word chapter could not be published as a post.

Calling it a book raised the standard, so he reworked the first 10 chapters, and the result became What's Our Problem?

How I Write

Publishing chapters first and sorting the criticism made the book stronger. Urban posted the first ten chapters as blog posts and read hundreds of comments. He discarded tribal and ad hominem attacks fast and kept substantive ones pointing out inconsistency, bias or missing the forest for the trees, then rebuilt the chapters tighter.

He invited one thorough commenter, Jacob Aziza, to read the draft and says the book is better because of him. "It's important to read those and to reflect on them."

How I Write▶ 20:21

Compress long research into only its best moments. Urban aims for what Julian Shapiro calls dopamine hit density: months of mostly bored or confused research squeezed so the reader feels only the highlights. He compares it to a stand-up special, a decade's funniest thoughts in one hour.

Hits can be a fascinating fact, a joke that lands, a conversation with a friend or a funny comparison. He cites Raymond Chandler's rule of one moment of insight on every 250-word page. "I'll research for three hours and get seven minutes of dopamine hits."

How I Write

If he enjoys rereading a piece, readers will too. He writes what he would love to be sent, then rereads it as a reader. He can tell when he is being boring and assumes the reader can as well.

He names three separate reasons for getting stuck: a daunting section, a messy structure, and dull prose he hates while writing it. He refuses to write a flat chronology of "and then this happened".

How I Write

Write the whole piece first and mark drawings in bold brackets. Wherever a drawing belongs, Urban types a bold bracketed description of it, which reminds him later and lets feedback readers picture it. The drawings come at the end as a grind, about six a day, like going to the gym.

He says he is not a good drawer, so each blank page raises the question of how to draw the idea. Stick-figure faces are subtle: one tiny extra curl of the mouth changes the expression.

How I Write▶ 25:18