Malcolm Gladwell

Malcolm Gladwell (@Gladwell) joined William Channer (@WilliamChanner) on the Dorm Room Tycoon podcast to talk about writing.

There were two legs for the body of this podcast about writing; how Malcolm Gladwell writes and Malcolm Gladwell’s advice for writing. I found both fascinating. I remember reading Gladwell in college and it was enlightening. Not the actual book per se, but the type of book.  Wow, I thought, why can’t we read this in school? His books are wide, clear, and bring together an interdisciplinary approach that many people advocate.

Tren Griffin spoke about interdisciplinary models for business. Sanjay Bakshi spoke about  interdisciplinary models for finance. Phil Rosenthal spoke about  interdisciplinary  models for writing. All of these accomplished people implicitly advocate for Gladwell’s books. Big ideas should be understood as multifaceted. Gladwell shines a light that makes those gems sparkle. Enough about my admiration for Gladwell. Let’s get to the notes.

How Malcolm Gladwell works.

Stumble around

“I tend to start with a puzzle,” Gladwell says, “part of my job description is to be on the lookout for stuff that fuels this exploration.” Gladwell reads books “by the truckload,” and is a fan of the Jack Reacher series.

Gladwell, like many other people featured here, reads widely. His initial phase might mimic what  Maria Popova said about search and research. In an interview with Copyblogger, Popova said:

“I just had tea with someone – a writer whose book I’d written about and who reached out and wanted to connect – and that hour-long conversation gave me a dozen ideas to think about, to learn about, and thus to write about (including two books I already ordered based on our chat). Is that “research” in the sense that one deliberately sets out to find something already of interest? No. Is it “research” in terms of the unguided curiosity that lets one discover something previously unknown and succumb to the intellectual restlessness of wanting to learn everything about it? Absolutely.”

She continued:

“And I think that’s part of our challenge today, not just semantically but also practically – we tend to conflate “research” with search, which is always driven by looking for something you already know you’re interested in; but I think the richest “research” is driven by discovery, that intersection of curiosity and serendipity that lets you expand your intellectual and creative comfort zone beyond what you already knew you were looking for.”

Gladwell says there is, “lots of stumbling. I depend on the stumbling.” What Gladwell is hoping to find is patterns of things. In David and Goliath for example, Gladwell drew in examples from; girls youth basketball, dyslexic CEO’s, and World War Two bombings. Superficially those things have nothing to do with each other. When Gladwell reads about each he dives deep and starts to see common threads under the surface.

Research however you’re comfortable.

Besides “stumbling,” how else does Gladwell work? In one word, comfortably. Gladwell, like Michael Mauboussin enjoys physical books because of the tactile and emotional memories in them. Gladwell says he can walk along his bookshelf, and “each book represents a set of ideas and observations and I know what’s around it.”

That doesn’t mean his way is the only way. Sanjay Bakshi said that digital books work better for him. His purpose (teaching) is different from Gladwell’s (writing).

Fivethirtyeight had a great podcast about the Bloomberg Terminal. It costs $2K a month, and it’s worth it for some people, but I got the impression it wasn’t worth it for everyone. So why hasn’t it been usurped? Switching costs are too high. Even though a rival system may cost less, it’ll take too long to understand. That’s how Gladwell view his process.

What makes a good idea.

Ideas need an element of excitement says Gladwell. For example, why isn’t global warming a bigger deal? “No one has found a way,” says Gladwell, “to tell that story so it seizes your imagination.” Well, one person has. Global warming, says Seth Godin should be called “atmoshphere cancer.” Godin explains, “I’m not being facetious. If the problem were called “Atmosphere cancer” or “Pollution death” the entire conversation would be framed in a different way.

There should be some sort of artistry and flamboyance in an idea Gladwell says. Scott Adams says he noticed then when writing God’s Debris and Dilbert. How do I keep the reader interested, Adams wondered. He did this by using hypnosis. Certain words can engage people in different ways Adams notes. The word “yank” is funnier than “pull” he says. Through words, Adams creates appetizing works. Gladwell orchestrates ideas. Both entertain and connect with their readers.

Editing and drafts.

“I do many, many, many drafts,” Gladwell says. A 6,000 word New Yorker article might take six months and go through seven or eight major versions. And it never comes out right at first.

“I have an expectation when I’m writing,” Gladwell says, “that it’s all going to change.” It’s like Legos Gladwell says. If you have kids, you know that making a Lego pirate ship isn’t enough. It needs to be a pirate ship with laser cannons and knights on horseback. Themes and ideas interlock easily with Legos. So too does Gladwell’s writing.

He says, “I think of writing as very modular.” Pieces can be put together or taken apart, and it’s no big deal. Except it was for Richard Thaler.

When Thaler was writing Misbehaving he had a problem. Much like Daniel Tvessky (who’s own biases about writing were outlined in the Jason Zweig post), Thaler had a problem. He didn’t want to edit his book.

He knew he had to, but he also knew he would be biased about what to take out. Any piece that he worked especially hard on, whether in research or writing, would probably have a sunk cost fallacy. That is, if Thaler devoted so much time to a certain section, he might be inclined to include it because of the investment rather than the merits. But, as a wily social scientist, Thaler had an idea.

Instead of cutting those sections, he moved them to a new document. They weren’t sections that were removed, but repurposed. It’s like when a kid brings home a Christmas art project from school and their parents delicately put it in with the other decorations. It’s being displayed, but only once a year. Good editing is best when you know thyself.

Know thyself.

Gladwell says that he doesn’t feel much pressure to write. “Everyday I’m running across something worthy of exploration,” he says. It echoes what Seth Rogen and Evan Goldberg and Anne Lamott said about writer’s block. It’s not a block so much as a gap. If you are exploring and thinking in new ways – if you are developing interdisciplinary approaches and mental models –  you’ll be stumped less.

Gladwell does this, but doesn’t think he needs to churn ideas into hits at the frequency a musician might. “My only test,” says Gladwell, “is, does this strike me as being novel and cool?”

Much like Chris Sacca, Gary Vaynerchuk, and Mark Cuban think about angel investing, Gladwell focuses on what interests him. When  Brett Steenbarger said, “figure out who you are when you are at your best,” this is what he was talking about. Gladwell knows what interests him and how to write about it. That said, he’s still trying to get better.

5 steps to be a better writer.

In this interview, Gladwell sounded aspirational. Not in a worried way, but in a I want to get better before I die way. Culled from different parts, here’s Gladwell’s advice.

1. Take risks. “I’m not sure the screenplay I wrote is any good,” Gladwell says, “but I am sure writing a screenplay made me a better writer.” Brian Koppelman said that he writes music for the same reason. Not because it’s good, but because it draws on something that makes him a better writer in other areas.

2. Make an existing skill better. Gladwell said that a few years ago he started taking narrative more seriously. He stopped what he was doing, and focused on improving one part of it. Astor and Danielle Teller did this when they wrote a book on marriage. They wanted one part of their life (marriage) to be better, so they deconstructed it.

3. Imitate. “I became very interested in the writing of Michael Lewis,” Gladwell says, “I would like to try his way and see what happens.” Gladwell’s capturing on the idea of imitation. He wants to write more like Lewis and see what happens. Jason Calacanis told Tim O’Reilly that he imitated everything he did to get started.

4. Work for a newspaper, but don’t stagnate. What? A dying form? Gladwell says that there is value in writing for a newspaper. It taught him to write quickly, to remove his ego, and to write a certain volume. “It used to take me ages to write,” says Gladwell, “then I worked at a newspaper for ten years and I was cured of that.” Gladwell practiced. Joshua Foer dove deep into practice, and deconstructed the crucial parts. But practice can’t stagnate, you need to move on. On Grantland Gladwell wrote:

“So why are the Jamaicans so good? There are many reasons, but the simplest is that the effect of peers on high performance are REALLY strong. In Jamaica, EVERYONE sprints. There are 20 heats in the 100-meter regional championships. And because everyone sprints, and the average quality of sprinting is so high, everyone’s expectations are raised accordingly. The psychological ceiling on elite performance if you are a high school sprinter in Kingston is, like, a foot higher than if you are a high school sprinter in America.”

Build your skills in a good place, but then move on to be around people who will make you better. Simon Rich said he wants to feel like he’s barely keeping up. Only then will he feel like the challenge level is right.

5. Learn to ask questions. Interviewing famous people can be hard. Gladwell said that when he interviewed Magnus Carlsen, he had to find the story. Even though Carlsen is the greatest chess player alive, the story still had to be chased down. “Know the first thing you want to know,” Gladwell says, but leave room for a conversation to flow.

Stephen King compared writing to digging up a fossil. King and Gladwell write at opposite ends of the spectrum of truth, but this part seems the same. King writes:

“Stories are relics, part of an undiscovered pre-existing world. The writer’s job is to use the tools in his or her toolbox to get as much of each one out of the ground intact as possible. Sometimes the fossil you uncover is small; a seashell. Sometimes it’s enormous, a Tyrannosaurus Rex with all those gigantic ribs and grinning teeth.”

Gladwell’s question suggestions is a method of of sweeping the fossil.

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Thanks for reading, I’m @mikedariano on Twitter.