On Creating Engaging Content, Reading, Writers, And Writing
What I’ve Learned — “Malcolm Gladwell Teaches Writing” MasterClass
Malcolm Gladwell, a journalist and writer best known for unique perspectives on popular culture including:
How social epidemics result from a combination of seemingly arbitrary contextual details (“The Tipping Point: How Little Things Can Make a Big Difference”). Common characteristics in what makes one successful (“Outliers: The Story of Success”). How perceived disadvantages are actually advantages (“David and Goliath: Underdogs, Misfits, and the Art of Battling Giants”)
What follows is a “quotes only” (a la Esquire’s “What I’ve Learned”) account of quote notes I took in consuming his MasterClass (hence my direct words in italics to differentiate).
Here’s what you’ll find…
- On Reading
- On Writers
(Criticism. Research. Interviewing.) - On Holding Readers/Captivating Content
- On Structure
(Titles. Tone and Voice.) - On Storytelling/Being Engaging
- On Writing/Creating Content
(Drafts and Revisions. Jargon. Humor and Melancholy. Writer’s Block.)
Quick word of caution. It seems to be human nature that the longer something is, the less impactful we see the individual and/or smaller parts. Don’t do that here. It’s long, obviously. But there are gems galore and much to explore in every part and piece.
On Reading
Read to Discover Intent. The way to keep your reader in mind as a writer is first and foremost to be a reader.
And when I say that, I don’t just mean someone who reads but I mean someone who takes the task of reading seriously.
The good reader is the one who says, ‘What did the author intend when he or she was reading this book?’ And if you feel like the author lives up to the intention, then the book is a success.
When you think about reading as an act as consequential as writing, it’s not a lesser act. You don’t read because you can’t write or you don’t want to write or you want to leave writing to others.
Reading is of equal importance to writing. There is no writing without reading.
If someone has shown you ways in which you can appreciate and reproduce a sense of wonder in yourself. I think that’s a much higher calling for a writer.
Reconstruct a Writer’s Thought Process Find a non-fiction book you really like and then go to the back and look at the sources that writer used and start reading some of those sources. So you’re putting yourself in the mind of the writer. You’ll see how people used sources to build a narrative.
Readers are not dumb. So one of the things you’re doing as you are reading something, your internal critic is asking the question, ‘Is this worth it? Is this a good use of time?’
You don’t read non-fiction for the same reason that you chew gum or watch the Kardashians on television. You read it because you’re in search of something powerful and fundamental about what it means to be a better person.
On Writers
Set a Reasonable Bar The most important thing is what is your expectation as a writer for how much you can write. It’s important to set a realistic expectation.
The feeling of failure that writers sometimes have is very often caused by the fact that they have too high an expectation for how much they can produce in a given day or sitting.
Differentiate Yourself Creating comparative advantage for yourself. What can I do to make sure that I’m different from everyone I’m competing with? That always should be the first question that you ask yourself. What is it about what I’m doing that will make me stand out? Not necessarily be better, that’s way too high a bar.
If you do something that catches people’s attention, the world will find you. Not always, but the world is pretty good at finding talent.
Writers are so weirdly defensive and self-protective and narcissistic about their work. Drives me crazy. Everyone should just relax and understand that everything we do is a function of little bits and pieces we’ve learned from others. And the sooner we accept that fact and have a little humility about our work the better off we’ll be.
Criticism
Don’t Mistake Critics For Your Audience The mistake you make when you are criticized is to think of your critic standing in for your audience.
People disagree with critics as much as they agree with them.
The critic, if they are unreasonably critical, does themselves a disservice. They remove their own legitimacy. They undermine their own legitimacy. And readers pick that up. They know what’s going on, they’re not dumb.
Critical reception is not a universal signifier of a flaw in the piece. It is simply a signifier of the opinion of the person who wrote the critical review.
Research
Follow The Footnotes They tell you how the person who wrote the thing you are reading thought. You can retrace their steps. Very often retracing someone else’s steps is an incredibly useful way to introduce yourself to a topic.
Another mistake people make is they assume that if something is not current, it’s not useful…
Nothing could be further from the truth. I almost feel like the better stuff is the older stuff. Particularly stuff that’s stood the test of time.
You could waste a lot of time messing around with things that are from the present day without realizing that most of it is crap and will be forgotten in five years. Why did you waste a week reading all this stuff that was generated in the last month when it’s going to disappear?
Get Off The Internet The very thing that makes you love Google is why Google is not that useful. Google has given me a dead end. I have my question, it answers my question. If I’m looking for a story, I don’t want a dead end. I want to be lead somewhere entirely new and unexpected.
The central challenge of the writer is the challenge you have at the beginning. What direction do I want to go in? That is where the computer is not your friend.
Following Your Curiosity. I think you have to feel free to go down roads that don’t lead anywhere immediately.
If you do enough of those of those little wanderings, then you have a shelf that’s packed with all kinds of really cool things. But doing something only because you can perceive in the moment that it might be useful is a really good way of not gathering anything at all. Because you cant know in the moment. That pressure is too high. Who knows what will come of some stray fact? You just have to be patient.
David Epstein: Depth of Research He communicates to you in a sophistication and depth of his writing just how much work he did, in other words you have full confidence as a reader he’s covered all of the bases.
Interviewing
Show Your Subjects Why They’re Interesting The central problem that all people have, particularly interesting people is that they’re not always aware of why they are interesting.
So the job of the writer is not to supply the ideas in any kind of encounter. It’s to be patient enough to find the ideas in any encounter. You just have to know where to look, where and how to listen, and know how to push people in the right direction and make sure they don’t go off on a tangent.
I bring myself to it and I bring my naïve self. I say, ‘Wait a minute, I’ve never heard of this before, how do you do that? What do people say when you say that?’ It’s about alerting people to those parts of their lives that may seem banal to them but in fact are not.
Make Your Subject Slow Down The word ‘wait’. Getting someone to slow down when they are talking to you solves all kind of problems simultaneously.
Use Humility As a Tactic Human beings have a moral obligation to pursue humility as a trait. We are better people when we are humble. It’s easier to learn. Easier to get along with others, appreciate the world around you. We are truer versions of ourselves and better friends and family to others when we’re not putting ourselves first.
The most interesting thing anyone can tell you in an interview is the unexpected thing. And if you have the list of questions in front of you that you’re devoted to, then you are closing doors before you started.
On Holding Readers (Captivating Content)
Your job as a writer is to create an environment where stories can be told. Sometimes that requires faking it, but actually 99.9% of the time it requires an honest examination of what you really did know.
The reader needs a tool sometimes to want to keep going, so give them one. Come up with a fun one. People don’t mind a little time out to learn the rules of the game. Then they’ll plunge back in with new enthusiasm.
Create a Connection to Data People mistakenly think of data as boring. As a kid what do you notice about data? Your first exposure of data is the grade you get on a test, that’s data.
This notion that we’re not interested in data is, if you’ve had your eyes open from the earliest beginning, completely false. The issue is do we have a connection to it. So all you need to do is create a connection, a reason to look at a row of numbers.
I will use charts and graphs in my writing all the time, but only when I’ve told you a story as to why the chart and graph is meaningful, and how to read the chart and graph.
Everyone likes numbers. It’s just a matter of preparing the reader to appreciate them.
Give the Reader Some Candy Once you understand that ‘talking about something’ and ‘thinking about something’ are different categories then you say, ‘Oh my task as a writer is to give you something to think about but also something to talk about, and they may not be the same’.
If that’s the way people communicate, then serve that need. Give them little moments. Give them little digressions that can be represented in the elevator that will help them kind of sell the piece to their friends or give them the opportunity to pleasurably talk about what they just consumed.
Example of Candy You do some little quirky biographical fact that kind of people like oh really, that’s so weird, I had no idea.
Cultivate Surprise. As a writer, your job is to get people to keep going.
Invite Readers To Guess The more opportunities you build into your pieces for reactions the better off you’re going to be. The more engaged they’ll be in the reading process and the more memorable what you’ve written will become.
Withhold Information With a Purpose Everyone wants the reader to keep reading. That’s the central struggle of the writer, to create something people will persist with, will keep on going past the point they would normally stop. One way is by withholding the prize until the end.
Play Surprise and Suspense Games Suspense is in large part a function of time. Suspense is the writer playing with expectations around time. Suspense is when you expect to have been told something by now and you haven’t been.
With suspense there’s certain questions I don’t answer.
There’s a crucial distinction between surprise and suspense. Surprise is where I tell you something and you had no idea it was coming or that you need to know it. Suspense is where you know that you need to know something and you haven’t been told. Similar but quite different.
On Structure
Structure is your friend. Not everything has to be done with language.
Don’t Complete The Puzzle The best kind of arguments are the arguments that are imperfect because the perfect argument is too obvious. The rule of the analogy is that the two things you are analogizing are not identical. To the extent they are too identical, the analogy is useless.
What draws you in is the imperfection. You don’t necessarily want the puzzle to be perfect at the end. You want it to be a little bit odd because that’s what attracts people’s attention. And that’s what makes them want to talk about it.
As a writer you want that response. You want to do something that irritates the reader, not in a serious way, but in a mild way. The way that when you put red pepper on something, the taste is a little harsh and there’s an aftertaste.
You want aftertaste. And that comes from not everything being perfectly blended together and all the pieces fitting so wonderfully it looks like a photograph.
What is interesting? That’s the question that has to drive writing, any kind of creative act. What do people find interesting? What does the writer find interesting? And what you find interesting is not perfection.
Make Promises You Don’t Keep I think it’s fine for narratives to be a little messy. I’m much more interested in the idea that someone might work through a problem imperfectly, or even fail at the task they’ve set out to do. But if the failure is interesting, I’m fine with it.
Being complete or being truthful to your intentions are not the same as being interesting. If it’s more interesting to go down a messy, dead end road, fine.
Write Sophisticated Ideas Using Short Sentences: Nassim Taleb My goal is to write at an 8th grade level but with ideas that are super sophisticated. It doesn’t mean what I’m writing is dumb, it means the way I’m writing is super simple and straight forward.
Writing should be simple enough that it does not defeat the reader.
The reader should never say, ‘Wait a minute, where did this sentence start?’
When you have lots of short sentences, when you want to do a long one, it really pops.
Establish Rhythm With Punctuation Punctuation is one of the ways in which you establish rhythm. It’s super important to read things aloud.
Don’t bury something great in a big sentence. If you want to have a punchline, make sure it ends the sentence.
Titles
Grab The Reader I’m fascinated by that notion of capturing someone’s attention. And that’s what a title is.
A title is, an even more edited attention grabber.
You should spend as much time thinking about titles as you do about content.
When you see two words in combination that aren’t supposed to be together, some part of you reacts. What’s going on? Something isn’t right. Capitalizing on that feeling you have that something is imperfect, not right, in conflict.
Think Of Your Title As An Ad A title is another example of time-constrained communication.
Tone and Voice
You cant hide your personality when you write, it comes out loud and clear.
Manage The Audience With Tone When you’re writing something, one thing you need to pay attention to is how is my tone coming across?
Mold Your Voice Based on Audience and Subject The language of sports is different from the language of other things. That your language as a writer is a function in part of who your audience is and the medium in which you’re writing, but also of the subject.
That’s what so lovely and important about sports. When I’m writing about sports I reflect that. In my other writing I would never call someone an idiot. I call Roger Goodell (NFL Commissioner) an idiot all the time.
Move Between Different Forms Your writing style is an instrument that needs to be honed and trained. One of the ways I think you can train is by moving back and forth between different forms. Between writing in a very, very buttoned up formal voice and writing in the most kind of freeing voice imaginable.
On Storytelling / Being Engaging
I think all good stories have one thing in common. That is, they have an ending — I don’t want to say satisfies because some great stories have unsatisfying endings which is why they’re great stories — but have an ending that transports you somewhere.
You have to be in a different place when you end than when you were in the beginning. And if all the story has done is taken you right back to the very place you were when you read the first sentence then it was a waste of your time. You have to have been challenged or transported in some way for the story to be a great story.
Look Where You’ve Looked Before Realizing interesting people don’t exist on an island, that no interesting person is by themselves. If you find an interesting person it means they are part of an interesting group and that is a crucial thing to remember when you are looking for story ideas.
Expand On The Critical Details In other words you have to read, I wasn’t just interested in their words, attending to their words, here I was interested in his prefix, where the words come from.
You can find gold in the smallest of details if you’re willing to.
That’s what the best kind of writing does, it identifies those kind of details that stand in for a much larger argument.
Test The Idea Itself The act of explaining an idea to somebody else is a good way to figure out how to tell the story and what parts of the story work and don’t.
When you tell a story in person, people are much more honest in their feedback than if you have them read a draft… There’s a million different responses that are incredibly useful to me that people will give you if you lower the bar, make it easy for them.
Hunt For Patterns A pattern is something that appears in different worlds simultaneously. You’ll see patterns so long as you inhabit different worlds. A pattern might be something that shows up in music, fashion, and sports. Those worlds are connected, but they don’t overlap.
So I always think of part of what I need to do in order to understand what’s going on is to make sure that I’m regularly leaving my own little island and visiting other islands.
I do think in my mind how important it is to trespass in foreign territories.
To me, part of the challenge with stories that are about ideas is framing them in a way that makes sense to people. That simply and quickly communicates to them what the idea is.
That’s a question that writers, non-fiction writers need to always ask themselves which is, ‘Is there an analogous world that’s dealt with this same question?’
On Writing (Creating Content)
That’s what almost all good non-fiction writing is about, giving us a window into other people’s hearts and souls and minds.
You want them to say, ‘That is me’ or even better, ‘That is a version of me I’ve never seen before, but I think it’s true. I think you’ve revealed something about me to myself’.
Let Go Of Your Ideas Once you’ve written something, it no longer belongs to you. It belongs to your readers.
In order for your work to be misconstrued, your work must first be read, so it’s better than being ignored.
If you’re misinterpreted, it’s probably your fault.
Drafts and Revisions
Just Get It Down The perfect is the enemy of the good is one of the most important aphorisms that I repeat to myself.
You have to accept the fact that your first couple of drops are going to be bad. They’re always bad. By definition they’re bad. You don’t know what you’re doing yet.
But it’s very important to go through the stage of just getting things on the page. Also, the act of explaining your argument or telling your story is how the story emerges. You figure out how to tell the story as you tell it necessarily.
You find ways to link things in the moment of writing.
Work Backward From Your Ending One of the mistakes I think writers make is they spend a lot of time thinking about how to start their stories and not a lot of time thinking about how to end them.
What do you need to know in reverse order to make sense of that song? What information do I want to withhold? Now that I know what my ending is, what will maximize audience surprise and suspense in listening? Other ways where I can divert my audience? They want to hear that, don’t give it to them.
The process of editing is always about simplification. If you are complexifying your argument during the revising process, then you’re writing in the wrong way. Your first draft should be complicated and messy, that’s what they are supposed to be. Then you go back and polish the jewel, get rid of all the impurities.
On Jargon
If you’re a writer and you’re trying to represent a world, a different world to your audience, the kind of jargon that is used to render complicated arguments more simply is incredibly useful to you. You should use that jargon.
The kind of jargon that is just simply people’s attempt to keep the world out and to be pretentious and to make them sound like they’re more expert than they are is the kind you should avoid.
Humor and Melancholy
When you’re producing laughter, you’re producing a very familiar emotion. Sadness, genuine sadness is quite rare. In a course of a given day, how many moments of genuine melancholy do you have? Very few. You might not have any.
There’s a reason why you can remember the last time you were very sad and probably can’t remember with accuracy the last time you laughed. Because laughter is cheap.
The task of producing, inducing strong emotions, sadness, melancholy in your audience is a very different task than the task of producing levity in your audience. I think of them as being at opposite ends of the continuum from one another.
If you think of that idea of sadness as authenticity, then rule number one is that no element of your description or discussion of that topic can be inauthentic.
So you can’t try too hard.
When you try too hard, you create doubt in the mind of the reader. The minute you have doubt, all is lost. They are out of the moment. They’ve taken a step back and said there’s something fishy about this, I thought the moment spoke for itself.
Writer’s Block
Just Keep Writing I never react to being stuck by stopping. I react to being stuck by either I jump ahead or redo something or I’ll write little pieces of an article without knowing where they fit.
Keep going. Because a lot of problems are resolved in the doing. Put it down on paper and it will invariably work itself out.
The task of a successful writer is to lower the bar. Avoid areas of high difficulty.
The great luxury of being a writer… We’re not surgeons. The world does not hold us to our first pass.
If we kill the heart patient, we just get to operate again. Make use of that extraordinary freedom.
Put It Down and Walk Away Perspective is your friend. And the only way to gain perspective is time.
