The Profile Dossier: Malcolm Gladwell, The Thinker Selling Good Ideas

As a complement to the regular Sunday newsletter, the Profile Dossier is a comprehensive deep-dive on a prominent individual. The dossier editions are only available to paying subscribers.

Malcolm Gladwell has been called “the best storyteller on the planet” and “the most spellbinding nonfiction writer of our time.” But it’s not his prose that’s striking — it’s the ideas he stitches together that pique our interest so profoundly.

Gladwell, a longtime staff writer for The New Yorker, has authored several books including, Blink, Outliers, The Tipping Point, David and Goliath, and Talking To Strangers. Gladwell’s strength lies in his ability to take disparate ideas across disciplines — sociology, psychology, medicine, and economics — and link them in a way that enables the reader see reality from a different perspective.

“What I’m really interested in is joy in intellectual play,” Gladwell says. “The unexpected turns that ideas can make is, to my mind, one of the greatest pleasures of being alive.” 

Over the last 20 years, Gladwell’s theories have served as conversation starters around the world. Below is a deep dive on some of his most interesting ideas including why talent is a myth, how we often misjudge the character of strangers, and what we can do to fall into intellectual rabbit holes.

(Photo credit: Bill Wadman)

READ.

On making ideas pleasurable: Gladwell is an intellectual hedonist: his big idea is that ideas should be pleasurable. Rather than trying to persuade you, he seeks to infect readers with his enthusiasm: Isn’t this interesting? But in a time of hyper-polarization and divisive public opinion, is what he’s saying enough to pique our interest? 

On dispelling the talent myth: A compelling New Yorker feature titled “The Talent Myth” put Gladwell on the map. In this fascinating story, Gladwell challenges the talent mindset of high-achieving organizations to hire, recruit, and promote “star employees” whose self-fulfillment might be in conflict with the best interests of the firm as a whole. This is a masterclass in leadership and management and why experience nearly always trumps raw talent.

LISTEN.

On the disparity between inner feelings and outward behavior: Gladwell has a theory he calls the “FRIENDS Fallacy.” He took an episode of the 1990s TV sitcom FRIENDS, and experimented with muting the show to see if he could follow the plot. “Everything that happens is expressed on the characters’ faces,” he says. “When Monica is angry, she looks angry. When Ross is perplexed, he looks perplexed.” Similarly, we assume that people’s emotions are reliably being broadcast to the world. “Turns out, that’s not true at all,” Gladwell says. Here’s why it’s important to understand that a person’s inner feelings don’t always match the way they behave.

On the elements of storytelling: Gladwell has what he calls “creative recipes” for storytelling. “For every hour I spend writing, I spend three hours thinking about writing,” he says. “I’m just putting down on the page what has already been kind of figured out in my head.” In this wide-ranging Tim Ferriss episode, Gladwell delves deep into his nuanced storytelling process, how he generates ideas, and what subjects qualify as interesting.

On challenging the idea of the lone genius: What makes an individual successful? In the United States, people tend to adhere to the idea that achievement is a largely individual act. However, in this podcast, Gladwell explains why we often overlook a successful person’s culture, family, and the idiosyncratic experiences of their upbringing. 

WATCH.

On choice and happiness: In this TED Talk, Gladwell explains what spaghetti sauce can teach us about happiness. If someone asks you what you want in a spaghetti sauce, you’d likely say you like it spicy or plain or cheesy. Very few would say they like it “extra chunky.” Yet! One third of the population loves extra chunky spaghetti sauce. Here’s the big lesson that the food industry discovered about human nature: People simply don't know what makes them happy.

On how he generates unconventional ideas: Gladwell’s writing doesn’t begin with characters or a plot or an event. It begins with a theory. In this interview, he explains how he once took a sociological theory about riots and used it to explain the rash of school shootings. “I wrote an entire piece about school shooters and never really mentioned guns,” he says. “I thought I could make my case much more cleanly if I stepped away from the gun part of it and focused on the social dynamics.” 

On the role of adversity in our lives: In his book David and Goliath, Gladwell challenges how we think about obstacles and disadvantages in our lives. He explores the question of why is it that sometimes the person we perceive to be the underdog is fully capable of defeating the giant? In this interview, Gladwell offers a new interpretation of what it means to be discriminated against, cope with a disability, lose a parent, or attend a mediocre school. 

On misjudging the character of strangers: In this Joe Rogan episode, Gladwell argues that there is something very wrong with the tools and strategies we use to make sense of our interactions with strangers. He uses the example of Sandra Bland’s traffic stop gone wrong to illustrate how often people mischaracterize a stranger and fail at discovering the truth. 

TECHNIQUES TO TRY.

Be interesting, not perfect: Gladwell says that people are often drawn to things that are done imperfectly. Whether it’s art, movies, or books, people talk more about the flawed things that get stuck in their heads than they do the obvious, perfect things. “You want an aftertaste, and that comes from not everything being perfectly blended together,” he says. “The question is: What is interesting? That’s what has to drive any creative act.”

Find meaning in your life’s work: Money is important, but it’s not the most important factor in leading a fulfilling life. In his book Outliers, Gladwell posits: “If I offered you a choice between being an architect for $75,000 a year and working in a tollbooth every day for the rest of your life for $100,000 a year, which would you take?” Probably the former. There are three things he says we need for our work to be satisfying: 1) autonomy, 2) complexity, and 3) a connection between effort and reward. Remember, he says, “Hard work is a prison sentence only if it does not have meaning.”

Fall into intellectual rabbit holes: If you want to unearth new ideas, get off the internet. On the internet, you’re part of social media platforms that often confirm your existing beliefs. If you type a question into Google, you’re served the most popular queries. So how do you uncover fresh new ideas? Gladwell says you need to create an environment that facilitates falling into intellectual rabbit holes. He offers three tips. First, take a walk through towns or buildings that pique your curiosity. Next, go to the library, identify books you’ve liked reading in the past, and look around them on the shelf to discover something new. Finally, look at the footnotes in books or articles because they often lead you to other sources that can help you learn the subject more intimately.

How to have an interesting conversation: The central problem most people have is that they don’t know why they’re interesting. Ask questions that draw out the strongest, most unique qualities in a person. Gladwell recommends being naive, humble, and using the word “wait” to slow down the conversation and allow the other party to flesh out their ideas. “Humility means saying, ‘I am more interested in you than I am in me for this conversation,’” he says. If you listen intently, you’re bound to have an interesting encounter. 

QUOTES TO REMEMBER. 

The key to good decision making is not knowledge. It is understanding. We are swimming in the former. We are desperately lacking in the latter.”

“If you work hard enough and assert yourself, and use your mind and imagination, you can shape the world to your desires.”

“It would be interesting to find out what goes on in that moment when someone looks at you and draws all sorts of conclusions.”

“Hard work is a prison sentence only if it does not have meaning.”

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