Notes from Malcolm Gladwell's writing Masterclass – Part 2

28 Feb 2019, 1900 Words

Here are my notes from Malcolm Gladwell’s writing course on Masterclass. It has 6 hours of dense video content, so these notes will be split into 4 parts published over 4 weeks.

Misrepresentation, misunderstanding, and miscommunication are on me. The good stuff is on Malcolm Gladwell.

Link to Part 1

Here’s part 2.

Get off the Internet

Interesting stuff comes when you’re not looking for it. Google tells you exactly what you’re looking for, and tells you all the things that other people already know and have already written about. Worse, it ranks them by popularity. This is not what you want when you’re looking to write something fresh.

To find a story, you want to be led somewhere unexpected. Finding the direction of a piece is the hard part, and Google can’t do that for you — it gives you dead ends.

Libraries are the opposite. Each book is surrounded by similar books — new avenues to explore. Each book has footnotes, letting you retrace the author’s steps. Librarians love helping you go through these. And you’ll need them to — most sources aren’t online. A 1988 paper will have sources from the 1950s, which themselves will have sources from the 1920s.

Follow your curiosity

In the moment, you can’t know what’s going to be useful. So follow your curiosity.

In the mid-90s, Malcolm read an article that described a town called Roseto. No one in the town seemed to die — there was no alcoholism, no heart attacks, no suicide, no depression . This was despite them all smoking and being overweight. Malcolm was curious about this, and visited the town. He chatted to the mayor and residents about why no one died in Roseto.

It turned out that Roseto’s story was already written — someone had conducted a medical study there and written a whole book about it. But Malcolm kept his notes and interview tapes anyway.

15 years later, Malcolm resurfaced Roseto as the opening story in his third book, Outliers. Feel free to wander.

Find stories that speak for themselves

Malcolm wrote a story about a kid who tried to blow up his school. School shootings are so common that this one didn’t make it into the media, but the would-be shooter gave a 5 hour interview to the police, with a full transcript online.

It was one of the most gripping, weird, and fascinating things Malcolm had ever heard. It was so good that the story practically wrote itself. All Malcolm added was a simple theory — that as school shootings become more and more common, the people who get swept up in them become more and more normal. (This kid was never out past 9pm.)

The rest of the story was in the transcript. For a writer, it was a beautifully wrapped gift. Malcolm was certain that no journalist had read that transcript before him, otherwise they would have written exactly the same article he wrote.

Malcolm can’t remember how he found this transcript — he was just trawling the internet.

Look where you’ve looked before

Look for new story ideas in the same places you got previous story ideas. Interesting people know other interesting people. Follow these connections to surface new ideas.

Dig into details

You can find gold in the smallest of details, if you’re willing to do some digging.

Malcolm once read a Harvard study about improving players’ health in the NFL. It recommended that the doctors on the field not be employed by the teams, because of a conflict of interest — teams are incentivised to keep players playing. (The NFL is notorious for killing its players).

Jeffrey Miller, the NFL’s Senior Vice President for Health & Safety, wrote a long rebuttal to this study. Jeffrey Miller, not Doctor Miller. Malcolm thought this was odd — surely the guy in charge of player health and safety was a physician?

It turned out that Jeffrey Miller wasn’t a doctor, but an anti-trust lawyer. The NFL hired him to make sure that the rising health crisis among players didn’t cause congress to take away the league’s anti-trust exemptions.

Once Malcolm discovered this, he was off to the races. This small detail perfectly represented a much larger argument about the NFL acting in contempt of player safety. It set the direction for the whole piece. And it all came out of wondering why people weren’t calling this guy Doctor Miller.

It’s hard to write in the first-person

The biographical voice is typically taken by people who’ve done extraordinary things — Hillary Clinton, Julius Caesar, Malcolm X. This makes the bar way higher.

Writing about yourself isn’t necessarily narcissistic, but it is self-indulgent. It raises suspicions — ”Who is this person who thinks they’re so interesting?“.

Malcolm’s written about his life very sparingly — “I’m not sure why someone should care about my life so much”. Stories about his life that can compete with the stories about other peoples’ lives, he says, are very few. There are maybe 2 or 3 of them, and they can only be told in a context where you can accept the diminished dimensions of his own personal narrative.

Talk to people about your ideas

Explaining an idea to somebody else is a really good way to figure out a story. Which parts work? Which parts don’t? When do their eyes glaze over? When do they ask questions?

If you tell them a story in person, people are more candid than if you give them a draft to read. Reading takes more effort, and if people know you’ve already gone through some work, they’ll be worried about hurting your feelings. When you’re telling a story in person, the bar for feedback is much lower — listeners will default to honesty.

The things that you find interesting and the things that the world finds interesting — they overlap, but not perfectly. Talking to people will tell you which of your ideas are in this overlap.

Grow your ideas

Everyone has random things on their mental shelves. Accessing these things is a great way to generate ideas. When you tell someone an idea, the “Oh, that reminds me of…” response is what you want.

Here’s one format for a good conversation:

I tell a story from my head. You respond with a connected story from your head. I respond with another connected story. Together, we build up a conversation stream like this, and if we’re good conversationalists, it progresses to something interesting.

If it doesn’t happen naturally, you can encourage this kind of conversation by just asking “What does this remind you of?”.

Experience the story

Some things you have to experience in order to have any chance of explaining in words.

Malcolm was writing a piece about JFK’s son, who died when the plane he was piloting crashed into the Atlantic. The flight investigation revealed that the plane had gone into a graveyard spiral dive — spinning in circles while descending rapidly. But in the cockpit, JFK Jr. was completely unaware.

Even with low visibility, how could a pilot not feel themselves spinning out of control?

Malcolm could only understand by feeling it himself. He went on a flight with an experienced pilot, who simulated a graveyard spiral. Pulling out of the dive with just 1.5 seconds to spare, the pilot asked whether Malcolm had felt anything off. He hadn’t.

Malcolm says this wasn’t a stunt, but the only way he could hope to describe something so hard to believe.

Leave your island

A pattern is something that appears in different worlds simultaneously. You’ll only pick up on patterns if you inhabit different worlds, so make sure you leave your island regularly.

The worlds of theology and endocrinology collided when Malcolm was writing David and Goliath:

Everyone’s familiar with the story of David and Goliath, so Malcolm wanted to take it to the next level. He dug into the theological literature to learn more about the story, but nothing new really came up. It was only by stumbling across a paper written by an Israeli endocrinologist that he found a different angle.

The Bible’s description of Goliath reminded the endocrinologist of a particular medical condition that causes overgrowth of the pituitary gland, leading to a loss of eyesight. To the endocrinologist, David didn’t just win by his smarts — Goliath also couldn’t see!

The giant, with all his size and power, had become blind.

This was the new angle Malcolm was looking for; the perfect metaphor for how underdogs win.

Show people why they’re interesting

People aren’t always aware of why they’re interesting. Something that’s profound and interesting to you might not seem profound and interesting to your interviewee — in their circles, it might be the norm. Alert people to parts of their lives that may seem banal to them, but in fact are not.

The job of the writer isn’t to supply the ideas in an encounter, it’s to be patient enough to find the ideas in any encounter.

Make your subject slow down

In an interview, you’re representing your readers. If you, the interviewer, have a question, then chances are that your readers will have that question too. If you don’t get something, say you don’t get it. If you find something fascinating, say so.

Wait is a powerful word. Getting someone to slow down solves lots of problems — it gives you time to think, it gives them a chance to expand on things, and overall, it gives you a better shot at understanding what they’re saying.

Use humility as a tactic

Humility allows you to navigate the world so much more easily. Interviews are much better when you adopt a tone of humility. When an interviewer tries to insert their own self into the conversation, it derails. Be genuinely interested in the other person; way more interested than you are in yourself.

Late night TV interviews, according to Malcolm, are not really interviews, since the host uses the guest as a springboard to show off their own charm and wit. There’s nothing wrong with this in the context of a late night talk show, but it’s not true interviewing.

Keep interviews short and unscripted

Interviewing well requires listening intently, and listening intently is hard work. Malcolm keeps interviews under 2 hours, coming back to them another day if required.

If you write out questions ahead of time, you assume you know what you want beforehand, and what the person is going to say. The most interesting things in an interview are the unexpected things. Don’t close doors before you start.

Get help with your weaknesses

Writers are independent contractors — everything is on you to do. But you don’t have to do it yourself.

Malcolm doesn’t like covering emotionally complicated terrain with his subjects. He finds it difficult to talk intimately to people with whom he’s not intimate. Once, for a story, he spent weeks trying to interview people in Belfast who lived through The Troubles. He didn’t get anywhere. Finally, he asked his assistant to try it, and within a couple of days she got everything he needed.

Outsource things to others. You don’t have to do everything yourself.

Part 3 of these notes will be published on 7 March. If you’d like a reminder, I’ll be sending a link out via Twitter and email 👇

thanks for reading!

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