Notes from Malcolm Gladwell's writing Masterclass – Part 1


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.

Here’s part 1.

Writing is a calling. A higher purpose. It’s part of the way in which we fulfill ourselves as human beings.

Don’t complete the puzzle

Writing is like a jigsaw puzzle. A story is a collection of different pieces, and your job is to arrange them in a compelling way.

In a jigsaw puzzle, every piece has to fit perfectly. In writing, it doesn’t. If something doesn’t quite fit, you can use writing to make it fit — you can write your way out of the problem.

The best narratives are the ones that are imperfect. When a puzzle is a little bit odd, it draws you in. People talk about the things that rubbed them a certain way; the things that didn’t go down the way they were supposed to. Those things stick.

Another angle on this:

Perfect analogies are too obvious — if I told you “cox apples are like pink lady apples”, it’s not terribly useful. If, however, I said that “apples are like oranges”, then we’re starting to get somewhere. Apples and oranges are normally unlike each other (“comparing apples and oranges”), so saying “apples are like oranges” is interesting.

It’s fine for a narrative to be a little messy, as long as it’s interesting. Perfection isn’t interesting, and being interesting is more important than being perfect.

“What’s interesting?” — this is the question that drives any creative act.

The Ketchup Conundrum illustrates a messy, but interesting narrative:

Most condiments have been reinvented over and over. There are all sorts of mustards, salts, vinegars… but there’s only ketchup — Heinz. Why haven’t any others caught on?

Malcolm set out to solve this mystery. He found a guy, Howard Moskowitz, the expert on grocery store foods. This is the guy who designed Diet Pepsi and Cherry Vanilla Dr Pepper, and formulated the optimal extra-chunky spaghetti sauce. Malcolm spent days with him discussing food varieties. He recorded every conversation to retain every insight. But when it came to ketchup, there were none. Not even Howard Moskowitz could solve the ketchup conundrum.

Malcolm had to decide what to do. The narrative had broken down — the Moskowitz piece no longer fit into the puzzle. But he wrote plenty about Moskowitz anyway, just because it was interesting.

After 5,000 words on the topic, Malcolm doesn’t end up resolving the ketchup conundrum:

Moskowitz shrugged. “I guess ketchup is ketchup.”

Use structure

Structure is your friend. You can use numbered sections to break up your work — don’t worry about making clever written transitions between different ideas. Not everything has to be done with language.

Complex ideas can be hard to communicate, so giving your readers the right tools can help. You can start a story, take a break to introduce a mental model/framework, then resume. Readers will instinctively want to apply the new tool you’ve given them, so they’ll not only understand the story better, but will also be much more engaged with it.

Use data

Don’t shy away from data. People do like numbers, as long as they’ve been prepared to appreciate them.

Our first exposure to data is at school, through test scores. This data is immediately interesting — everyone wants to know what everyone else got on the test. Malcolm talks about one of his classes, in which the teacher would seat the students according to their scores, from highest to lowest — a physical chart. This wasn’t very nice, but it got everyone’s attention. The students would obsess over it.

Data is interesting as long as we feel a connection to it and understand what it really means.

Give the reader some candy

Thinking about something and talking about something are different things.

The way we think about things is complicated, sometimes incoherent, and often contradictory. Articulating our thoughts can be really hard. So the things we talk about end up being the things we can talk about: the things we can remember; the things we can express; the things we can say in a short period of time while we have the stage in a conversation.

The thing readers will think about is different to what they’ll talk about. Your task as a writer is to give them both.

In a story, candy is the stuff that people will talk about, and the meal is the things they’ll dwell on and process more deeply. It’s fine to have candy, as long as you have the main meal, and it’s a bad idea to have one without the other. Candy helps people sell your piece to their friends. It can bring new readers to your work, and the meal will hold them there.

Malcolm likes quirky biographical facts (“So-and-so’s mother happens to be the same person as…”) and funny anecdotes as candy. Neither serve any narrative function, but they’re memorable.

Cultivate surprise

We tell stories for the reward of surprising others — seeing their reaction when they discover something new. Malcolm has a friend who, whenever he tells her something he thinks is interesting, acts like it’s not a surprise. “Oh yeah, I knew that”. Don’t be this person.

When someone tells you a story, they’re taking a risk — a risk that you won’t be surprised; a risk that you’ll be bored. If you respond dismissively, they’ll eventually stop telling you stories. But if you respond enthusiastically they’ll want to tell you more! As a writer, it’s your job to create an environment in which stories can be told.

But this doesn’t mean “faking it”. 99.9% of the time, it actually means making an honest assessment of what you really know. If someone tells us a story and we already know 75% of it, it’s tempting to give ourselves credit for all of it — “oh yeah, I knew that”. We should stop this impulse. Even if it’s just 2% that we didn’t know, we should reward others for showing us the world from a slightly different angle.

Invite the reader in

Elicit reactions from readers by making them an active part of your story.

Malcolm has a piece about suicide rates in England, in which he poses a puzzle. Instead of framing it as “This is a puzzle that criminologists faced at the time…”, he invites the reader in — ”Here’s a puzzle for you… what do you think?“. This is more engaging, and creates an opportunity for a reaction — most people think the answer is X, so it will surprise the reader when it turns out to be Y. This reveal has much more impact when the reader is a participant rather than an onlooker.

Invite readers to identify themselves. If you describe something in abstract terms — “Some people have a tendency to do X…” — people won’t identify it with their own lives. But if you describe it in a way that’s personal — ”I have a friend that does X…” — then readers will put themselves in your shoes.

The central struggle of writing is to create something that people will persist with, and you can encourage persistence by strategically withholding information. When a reader knows they need to know something, they’ll keep reading until they know it.

The best storytellers, in writing and otherwise, hold their audience by playing games of surprise and suspense.

Part 2 of these notes will be published on 28 February. If you’d like a reminder, I’ll be sending a link out via Twitter and email 👇