in: Behavior, Character, Podcast

• Last updated: September 29, 2021

Podcast #224: Why Smart People Do Dumb Things

Why do smart people do dumb things?

This is one of the many questions my guest has explored during his writing career. Malcolm Gladwell is a writer at the New Yorker, the author of several New York Times bestselling books, and now host of the podcast Revisionist HistoryToday on the podcast, Malcolm and I explore the question of why smart people do dumb things by looking at, among other things, the basketball career of Wilt Chamberlain. We discuss how Wilt discovered a way to increase his free-throw shooting percentage dramatically, but why he consciously decided not to continue using that technique.

We also discuss why going to elite colleges can actually backfire on you, and the criteria you should use when picking a college that doesn’t involve school rankings. I also ask Malcolm about his writing process, how to ask better questions, and how to find insights in the mundane. This is a great discussion with a fascinating mind. You don’t want to miss this!

Show Highlights

  • How to develop the curiosity of Malcolm Gladwell
  • How to ask good questions
  • The art of simplifying complex ideas
  • How the granny shot turned Wilt Chamberlain into a nearly unstoppable basketball player, but why he purposely stopped using it
  • How the sociology of thresholds keeps people from doing the things that will help them succeed
  • How to overcome social pressure so you do the thing you know you need to do
  • What a basketball team of 12-year-old girls can teach you about overcoming social pressure
  • Why deciding to go to a prestigious school can kill your academic career
  • The criteria young people should use when selecting a school
  • Why going to a prestigious school won’t give you much of long-term edge in your career
  • The boom in education philanthropy during the past ten years and why Malcolm thinks it’s being done poorly
  • Why we tend to be rational when it comes to stock investing, but not philanthropy
  • Malcolm’s competitive running career and how it helps him with writing
  • And much more!

Resources/Studies/People Mentioned in Podcast

Malcolm Gladwell Revisionist History banner.

If you haven’t already, pick up one of Gladwell’s books and give it a read. He does a masterful job of pulling out amazing insights from topics as mundane as ketchup varieties. Also, check out his new podcast Revisionist History. I’ve listened to every single episode so far and none have disappointed.

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Read the Transcript

Brett McKay: Welcome to another edition of The Art of Manliness podcast. Why do we sometimes not do the thing we know that works or works better? We’ve all probably had instances in our lives where we knew there’s a better to achieve our goal or achieve success, but we don’t do it. Why? Why is that? Well, that’s one of the many questions my guest today has explored in his writing career. His name is Malcolm Gladwell. Many of you have probably read some of his books like Outliers or Tipping Point or David and Goliath. Malcolm’s got a new podcast out called Revisionist History where he goes back in history to uncover overlooked or misinterpreted stories and pulls insight from them so we can apply them to our lives today, or at least think about them.

Today on the show, Malcolm and I discuss how Wilt Chamberlain found a better way to shoot free throws that increases free throw percentage rate considerably, but he purposely decided to stop doing it, and what we can learn from him on avoiding that mistake. We also discuss the art of finding insightful stories in the mundane, asking good questions, and why you might want to decline that acceptance to a prestigious university. Lots of stuff to chew on in this podcast. After you’re done, check out the show notes at

Malcolm Gladwell, welcome to the show.

Gladwell: Thank you. I’m happy to be on here.

Brett McKay: Well, I’ve long been a fan of your work, and I’m enjoying your new podcast, Revisionist History, and we’ll talk about that today, because you’ve got some great topics you’re delving into, but I’d like to meta first because I’ve been curious about this. You’ve made a career out of taking what seems on the surface very mundane or obscure stories. You’ve written on infomercials or ketchup, but then you show how they can provide insights into complex problems that cut across domains. I’m curious. What’s your process of going about that? It seems like it requires a lot of curiosity. How did you develop that curiosity?

Gladwell: I never know how to answer that question. I’m a little bit of a magpie, so I collect ideas and quirky stories and things and puzzle over them for a long time to figure out how they could be useful. A lot of it is just I have a big random group of things that I’m always looking to find a home for. Also, I think because I’m not an expert in anything, I move horizontally through ideas, not vertically. If you think about it, I’ve never written a book, or even an article, almost never, that was solely about one thing. I don’t go deep. I go wide. I am just puzzled by people who go deep.

When I look at someone who writes an entire book about a single subject and goes into fascinating detail, I always wonder, “How on the Earth did they do that?” It’s just not my-

Brett McKay: Right. Like about the toothpick or something like that.

Gladwell: Yeah. Not my way of thinking about the world.

Brett McKay: It seems like it requires asking good questions. One thing I remember in What the Dog Saw, you talked about there are certain people you want to ask questions, like the higher ups. People at the top of the chain aren’t usually the ones you want to ask questions. It’s in the middle. Why are people who are in the middle or who are actually doing the work the best people to ask questions?

Gladwell: Yeah. Because they’re seeing things from a different perspective and they are freed of certain kinds of constraints. Just to give you an example, there was a quote that came out from the Rand Corporation some months ago that was talking about how that staff at the SEC had increased dramatically in size over the last couple of years. Having a conference and I told them I would do a Q&A at the conference about this report, what happens to decision making when there’s more people. The question that came up, who should be doing the Q&A with, do we want to get someone way, way high at the NFC or do you want to get someone in the middle. A nice sentence was actually you want the person in the middle because they actually see the … you want to get into the nitty-gritty of what happens when you make crucial time with the decisions with 50 people and before you used to do it with 6. I want to know what that feels like. I don’t know, is that good, is that bad, is it …

I was doing mundane things like is it harder to schedule a meeting [inaudible 00:05:47]? Does that mean you can’t have a meeting as quickly? Is it harder or less hard to reach consensus? You’re not actually interested on what they couldn’t tell you what the subject and the meaning was. Anyway yeah, I only care about the subject. What I want to know is just what happens to people when they’re in a different sort of context. The person who could answer that question, I almost want to talk to … I just want to go as low as I can. I almost want the person sitting in a corner who didn’t say anything at all, just was taking notes. I don’t know if we can get that low but the person who led the meeting has a completely different … they are thinking about the politics side too. They have to report to the sensitivities and the materials.

They’re not who we want in this instance. Maybe if I’m a national security reporter for the New York Times, I do want that person because my goal is to find out what came out of the meeting, what the decision was. It’s different. It’s not what has drawn me to this example. It’s just the kind of … it depends on what questions you’re asking and because I’m very interested in process questions, it means I’m very often not interested in the person.

Brett McKay: Another thing I think you’re really good at is taking really complex ideas and simplifying them for these regular folks to understand. I think that’s actually a really important skill for people to develop because our society, economy is becoming more and more complex. I’m curious, do you have a process that you go through to simplify complex ideas?

Gladwell: No, but it was very much a part of my upbringing. My mother is someone who’s among other things a writer, and writes something in an incredibly clear and transparent way. I remember as a child being very kind of taken by how clear her writing was. She was a model for me. Then my father, who’s, from talking to people in his field, I came to understand that he was someone whose specialty was he would take the 10-page proof and turn it into a 3-page proof. I still feel it in my blood somehow to want to …

He would teach me math as a child and would take something that was hopelessly befuddled about and resolve it and explain it in an incredibly elegant simple way. I think I just came to think about is the highest form of communication is to … I remember even as a small boy, like many boys, endlessly play board games and card games and I would always insist on being the one who explained the game to everyone else since they hadn’t played it before because I was always convinced I could explain it to anybody else and I could even explain it better than the instructions. I always found instructions lacking. You know how you get in your board game and you’re like 8 years old you read the instructions and they make no sense. This infuriate me. The way they were written would infuriate with me and I’ve always had my own way of explaining how they worked.

Brett McKay: Right. Then again, it’s because you’re focused on processes again is that you have and you mentioned earlier.

Gladwell: Yeah. No, like even the very simple thing, instructions on games, the first thing you should tell, you should say is what the point of the game is. What is winning in this game? They wouldn’t do that. The first line should be in monopoly, the winner is the person who … and then explain the rules. Somehow they would feel like the point of the game is supposed to emerge from an understanding of the rules, which strikes me as crazy, completely backwards. I guess I’ve been doing this all my life.

Brett McKay: Doing your entire life, that’s really interesting. Let’s talk about some of the things you’ve written about and what you’re doing on your podcast now. As I read your work and as I’ve been listening to your podcast Revisionist History, it seems like a common idea that you explore is why people, they’ll know what they need to do that there’s a better way to do something but they don’t do it. You explore this idea that I thought was completely fascinating in your podcast about the granny shot in basketball. Can you talk about what we can learn about why humans sort of self-sabotage themselves from Wilt Chamberlain and the granny shot?

Gladwell: Yeah, that was the first episode. It’s funny, I didn’t think that was one of the stronger episodes and yet it seems to be the one that people, listeners have gravitated to the most, which just shows you what a bad judge you are of one’s own work. I was reading, I can’t remember why, a really interesting book on Wilt Chamberlain and it just describes his greatest game, his 100-point game in 1962 I think. Still the greatest basketball game anyone’s ever played and he shot 28 for 32 from the line, which is weird because he was famously a terrible free throw shooter. Then you keep reading, wait, that season was one of the only seasons in his career where he consistently shot underhand because his team had brought in a famous, one of those famous old school … actually a guy from the, what was that called, I think the Hebrew League. The Jewish Basketball League of Philadelphia, a guy named Cy Castleman, famous free throw shooter who shot under hand. It was brought into coach this way of shooting and all of a sudden Wilt Chamberlain becomes a fantastic free throw shooter.

The first thing he does after becoming a fantastic free throw shooter is go back to shooting the old way so he could be a terrible one again, which struck me as being so bizarre that I thought … but also more than just bizarre, so typical of human being. We don’t always do the thing that’s right or correct for us or best. We’re very often quite happy to go back and do the thing that got us into trouble. There’s a million examples. People who have a problem with alcohol relapse. We all bad habits, we know they’re bad and we persist on doing them. I thought it will be very interesting to use the free throw story as a way of talking about that, their human tendency to behave stupidly even when we know better.

It’s distinct from we do stupid things all the time just because we don’t know better, but we also do stupid things and we do know better and so I wanted that second case. What made the show work I think is I went and interviewed Rick Barry who was one of the few basketball players every consistently used the underhanded free throw. He would do it even though he was unamused so it’s not reviled but made fun of for using this kind of awkward shot. He turns out to be this incredibly compelling character, and so the episode is just all about Wilt Chamberlain and Rick Barry and then trying to make sense of why is it that some people can do some kind of … because first, be willing to try some new idea and the rest of us are hostiles.

Brett McKay: Right, and you talk about you get into that whole idea in sociology of thresholds where some of us need a lot of people to be doing something before we like yeah, I’ll do that too.

Gladwell: Yeah. If you think about it, it’s kind of a peer pressure model that some people, all of us will do even the most ridiculous if enough people are also doing a ridiculous thing. Some people don’t require a lot to go first before they act, and that difference in how many people, how many of your peers need to be doing something before you’ll join in is called low threshold. The low threshold people don’t need a lot of others to go first and the high threshold people need the world to go first before they could join in.

Wilt Chamberlain was a high threshold person. He was not going to continue shooting the underhanded free throw if he was going to be the only one or one of the only people. He didn’t want to stand out in that way. Whereas Rick Barry is someone who was quite happy being the only person in the NBA to shoot that way. It doesn’t bother him if he’s that kind of … his whole career, he persisted in doing things that set him apart from others. That way of understanding our behavior is really interesting because it frames our choices in social terms. It says the reason you do certain things may have nothing to do with the quality of the idea or your own personal preference. It just has to do with the social context that your 18-year-old son will drive 100 miles an hour while drunk even though he knows that it’s a terrible idea if he’s in a car full of his friends who are all drunk and urging him to drive 100 miles an hour. It’s just social. He doesn’t want to do it. He doesn’t believe in that. He’s also smarter than that, but in the moment surrounded by his peers egging him on, he’s capable of doing something very stupid. That is a profoundly human reaction.

Brett McKay: I’m curious. When you researched, have you found anything where you can inculcate an antidote to that or you can actually raise your threshold to where you’ll just do something even if other people are saying don’t do that or do this?

Gladwell: There’s a great example of this in binge drinking on campus that what people … this is one of the single most effective interventions against drinking on campus. They asked students what percentage of students they thought engaged in binge drinking. Most students said they thought it was something like 60% or 70% of all the students. They thought that binge drinking was something the majority did and so that’s why they did it. They felt they were … to not binge drink would be to stand out. Then they informed them that the real number is actually something like 20%. It’s a minority, and just telling students that something they thought was something everyone did was actually something that very few people did traumatically reduced the instance of binge drinking.

There, what you’re doing is you’re playing the thresholds. You’re saying that a behavior that people thought was common place was actually rare, and the minute you say that a behavior is rare a social context in which that behavior occurs changes dramatically.

Brett McKay: That’s interesting. I’ve heard a similar study with that with hookup culture, where they’ll ask students how many of your peers do you think are engaging in sexual relationships like on the first date and everyone thought everyone was doing it. But then they informed them no, it’s actually a small percentage and then that reduced the amount of-

Gladwell: Yeah, it’s the same. It’s a remarkably effective way of … same thing happens. If you think about something simple like wearing your seatbelt. Americans who are resistant for years to wearing their seatbelts, but now it’s second nature. Now if you don’t wear your seatbelt, you stand out so much that it’s almost impossible not to buckle up. Can you imagine … I can’t remember being in a car where someone wasn’t wearing a seatbelt. Everyone would remark on it. They would think you are weird and strange. The kind of social pressure now around wearing your seatbelt is overwhelming. That was not true in 1980.

Brett McKay: Yeah. You exposed this idea of people knowing what they should do. There’s a better way to do something, they don’t do it. You also hit on this a bit in David and Goliath where you talked about again basketball but there’s a team of 12-year-old girls who were utilizing the full-court press all the time to win basketball games. That seems to be related. No one else does it but this one team decided that this is what they’re going to do.

Gladwell: Yeah. Basketball teams, particularly youth girls basketball teams, going to play that way because it’s obnoxious. If you press again the group of 12-year-old girls, they won’t be able to get the ball up the court. You can’t actually play basketball if you press 100% of the time against relatively non-elite, even boys basketball of that age. The game becomes impossible to play so you have to be willing to disrupt the game in a really profound way to play that way. You have to be pretty bold and thick-skinned because the other team, the other parents particularly, are really getting angry because no one’s shooting. It’s just all turnovers. That was the funny thing was that this established strategy that … it’s a strategy that requires at least in the beginning some pretty thick-skinned obnoxious people to pull off.

Brett McKay: Right. You’re talking about Rick Barry, he was sort of thick-skinned and obnoxious. He didn’t have a really good reputation. You talked about his biography, his quotes from his parents who just like eviscerated him a little bit and he was okay with that.

Gladwell: He didn’t care what people think about him. I actually thought he was a nice good person, but he just doesn’t … the rest of us spend a lot of time doing things and saying things that we think will win the approval of those around us. He does not. It’s just not even on the table. He does what he think is right and that is a really sure way to make enemies. He went on and on about how … and he’s absolutely right. He does not understand why in the NBA, when someone misses a free throw, all the members of his team congratulate him. He’s like why are you congratulating … the guy just blew it. He just botched an incredibly important and straightforward play then you’re reinforcing his mistake by patting him on the back and high fiving him and doing whatever you do. He’s like that’s crazy, you should be doing the opposite. You should be shaming this guy for admitting the free throw.

He’s right. I’m like why are you congratulating someone for screwing up. You’re creating a social context in which people don’t feel they have to be great free throw shooters, but you can see why somebody who feels that way would be ostracized on a basketball team. Rick Barry would be the guy glaring at …

Brett McKay: It’s all social.

Gladwell: … that Dwight Howard for missing a free throw in the final minute of a game. That’s not going to endear you to be like Howard.

Brett McKay: Malcolm, something I’ve noticed, you’re very passionate about education, particularly education philanthropy. I saw the tweet storm that you did a while back ago. I have 2 questions related to education because I think they’re connected in a way. In David and Goliath, you talk about how the way many college students go about deciding which college to attend actually can stunt their academic growth. Can you flesh that idea out a bit?

Gladwell: Yeah, that’s called big fish in the pond theory and it says that it just is a psychological observation that it’s really hard to be in the bottom half of any classroom. It really makes it difficult for you to remain confident, to learn what you need to learn, to persevere, and there’s all kinds of evidence for this. Putting a student in a situation where he or she is in the bottom half, it’s perilous. It’s not always bad, it just increases the chances that particularly if you’re engaging something that’s very difficult that your going to drop out. I used the example of science and math classes. It’s really hard to be in the bottom half of a difficult math class.

When we look at why dropout rates are so high in science and math education, and they are extremely high, that’s what’s happening is that if you’re taking calculus and you’re the worst person, you’re the worst student in the class, chances if you’re finishing the year in that class or just minimal. What that says is the best place, the best environment to be when you’re looking for a college is not the most elite college you can get into but the college that where your chances of being in the top half are greatest. The best college for you is not the best college you can get into. That is-

Brett McKay: Right. If there’s a choice between an Ivy League school and a state school, go with the state school.

Gladwell: Sometimes. Many people will be better off in a state school because you’ll be in a situation where you feel much more confident so your chances of getting a science career or a law degree or a medical degree or what have you may be much greater in a non-elite place than in an elite place. That consideration, that simple rule I think is very often ignored and students are so obsessed with the kind of getting into the most prestigious school they can that they forget that the most prestigious school may not be the best school for you.

Brett McKay: Right. Haven’t they done studies where they found that looking at long-term trends, I know they’ve done this with law school at least that which school you attended overall doesn’t affect how well you do as a lawyer later on. You can go to a state school and you’ve done just as well financially as a kid who went to Harvard.

Gladwell: Yeah. Generally speaking when people do, economists do very careful studies of the usefulness of an elite education what they discover is that it’s not as useful as you think so that it’s really people from Harvard do well because the kind of person that goes to Harvard does well in the world. They would do just as well if they … it’s not Harvard in other words is making them succeed in life. It’s the fact that they’re very very smart, talented person and so it’s their personal characteristics, not the characteristics of their school that are predictive of their success. Once you account for that, you realize the additional advantage that accrues from the reputation of your undergraduate school is small. We exaggerate it, which is not the case. It makes a huge amount of difference where you go.

Brett McKay: It just makes you feel of being in the moment saying that I got accepted to Brown, that’s where I’m going to go. I think this idea is connected to a recent podcast episode you did on Revisionist History, this idea that going with the most prestigious school can backfire on a person and individually it also seems it’s connected to an idea of how education philanthropy is done. In the past 20 years, there’s been a boom in donations to American universities, big donations, but you argue that the way it’s done is actually not all that productive. Why is that?

Gladwell: There’s been this dramatic uptick in large gifts, so $100 million gifts to American institutions. They have overwhelmingly gone to schools that are already rich so the last two $400 million donations in the world of higher ed, Phil Knight’s gifts and John Paulson’s gifts to Harvard went to schools with an endowment of $22 billion and $36 billion respectively. People are giving lots of money to schools that already have lots of money and that episode of Revisionist History said first of all why, that’s kind of crazy. Why would you … what sense does it make to give money to people who are already rich? The institutions are already rich. It’ll be like me writing a check to Bill Gates, why would I do that.

The second point, so the broader point is that when we give money away we usually give a kind of return on our investment calculation where we say how much good can be purchased with my money. My argument is that if you give $400 million to a school that already has $36 billion, there’s not much more they can do with that money. They’ve already, presumably if you have that much money in the bank, they’re already doing the kinds of things that money can buy. They’ve already set up the lab, they’ve already funded the research, they’ve already supported the student in financial aid. Whereas if you give that $400 million to a school that has $100 billion in the bank, there’s an amazing amount they can do with that money.

Your return on your investments can give money to a needy school, it’s just vastly greater than if you give money to a wealthy school just as it would be in real life if you’re giving money away. The person living at the poverty line can do an extraordinary amount with $1,000. $1,000 given to a billionaire is meaningless. My puzzle that I’m trying to solve in that episode is why on earth, there’s this very common sense principle which is very clear when it comes to people. Why on earth is that ignored when it comes to giving to institutions.

Brett McKay: There seems like a little bit of that Matthew effect going on, like success, we just want to go with the winner so we give them more.

Gladwell: Yeah, which makes no sense. I actually said in an interview recently I thought that anyone who gives money to Princeton which is on a per capita basis, the wealthiest educational institution in the history of mankind, anyone who gives money to Princeton is committing a crime. It’s wrong, there’s no other way around it. Might as well just burn your money if you’re going to … it’s a tiny school, but on a per capita basis they are … they’re like one of those little islands in the South Pacific where every one millionaire.

Brett McKay: As you’re describing that, you made me think of stocks. Stocks, like the idea is that you want to … one of the things you do is you find the stocks are undervalued and you invest in that. That makes sense to people, I think like the schools that are poor or don’t have that much money or the undervalued stock. There are a lot of opportunity for growth and in the investing world, you don’t want to invest in the company that’s overpriced or has already reached its peak price. That’s what seems people do with philanthropy.

Gladwell: Yes, that’s exactly right. That kind of … it’s funny, so this is another area where in certain realms, I think we think rationally or at least we tend to think rationally. In other areas, so we think rationally about stocks usually but when it comes to educational funds plp are completely unwilling to … or not always, but many people, many wealthy people who are normally very thoughtful and intelligent are unwilling to use their same … think as rationally when it comes to their educational giving.

Brett McKay: It’s interesting. Malcolm, one thing just shifting gears here a bit. I think one thing a lot of people don’t know about you is that you’re an avid runner. In fact, I just learned this, 2 years ago you are 50 years old, you ran a 4-minute 54-second mile. It blows my mind because it takes me like 13 minutes to run a mile. When did you start running and I’m curious, is there anything you’ve learned from running that you apply to your work as a writer?

Gladwell: I ran a lot in high school very successful and then I stopped and really didn’t race again for 30 years. Although I ran a little bit but I decided to run seriously again in my 50s. Running is about … I don’t know if there’s a direct overlap with writing except that it gives you … it’s a standard period of time for reflection. I just think if you’re going to be a successful writer, you need to have extended periods of reflection. You go for a 10-mile run, I could go to hour and change that you have with your … that you’re alone with your thoughts and so that can be … there’s a nice overlap between the opportunity given by a long run and the requirements of writing.

Brett McKay: Malcolm, this has been a great conversation. Where can people learn more about your work and your podcast Revisionist History?

Gladwell: We have a website,, where all the episodes are available for download and I have a website,, where a lot of my writing is archived. I think between the two of those, you can pretty much get the full story.

Brett McKay: Fantastic. Malcolm Gladwell, thank you so much for your time. It’s been a pleasure.

Gladwell: Great. Yeah, it’s been really fun. Thank you.

Brett McKay: My guest here is Malcolm Gladwell. He’s the author of several books, you can find on Let me share his new podcast Revisionist History. You can go to to download episodes there or search for it on iTunes. It’s a really great show. Also check out the show notes for this podcast at

That wraps up another edition of the Art of Manliness podcast. For more manly tips and advice, make sure to check out the Art of Manliness website at and if you enjoy this show, have got something out of it, I’d appreciate if you give us a review on iTunes. It helps us out a lot. As always, thank you for your continuous support and until next time this Brett McKay telling you to stay manly.

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