The Exchanges

Q How has your mindset changed or stayed the same on the way we work? You know, I know you've said previously remote work is really not very helpful for you or healthy. Do you still think that's true?

A Well, I got, I got, I got in trouble because I, I overstated my argument. What I meant to say was When I look at my own career, I would not be where I am today if in my twenties and thirties I was working remotely. I went into the office every day in my twenties at the Washington Post, and I sat within You know, 10 feet of some of the greatest journalists of my generation. And that experience was in, of incalculable importance in teaching me what I'm doing. And if I was at home, I would have gotten none of it. Um, if I was at home, I would have missed the kind of serendipitous learning opportunities. I would have missed the kind of assignments that come just because you're around. Hey, this just happened. Somebody looks up and sees me. Gladwell, go do it. Unbelievable opportunity, right? If I'm at home, and they, they see somebody else, right? It's that kind of, Bob Woodward, the greatest investigative reporter of the 20th century, was 10 feet from me when I started as a twenty-two-year-old at the, twenty-three-year-old at the Washington Post. And I, I would spend hours just listening to him, just, just listening and watching him, listening to him on the telephone. It's like a graduate school seminar in how to ask questions, in how to Convince sources to do what you want them to do, how to, you know, I mean, on and on. I was just, I had a woman next to me, woman, Kathleen Day, …

AI assessment note: “I got in trouble because I, I overstated my argument. What I meant to say”

Q What do you think makes a good leader versus a bad leader?

A Well, I'm gonna cheat and say it depends. Um, it really depends on the nature of the leadership challenge. So, uh, I did this, uh, episode of my podcast with, um, the, with the former Chief of Staff of the Air Force, and the former Secretary of the Air Force, and they were talking about a mistake they made when they were working together in the Air Force, and they had written a book about leadership, which is where I read the story, and their notion of what effective leadership was, was servant leadership, that They had to put the institution first and themselves second. But there's a reason they say that, and that is that they were leaders in the Air Force, which is an institution with a 80 year history, ah, with an extraordinary amount of talent, Working for them. A very, very large organization doing a million different things where there's no way the, the chief executive can be expert in all the things the Air Force is doing, or even know what all the things the Air Force is doing. You know, I could go on, a very, very strong culture that they inherited, they did not create. Right? So all those circumstances mean you don't want Some fiery, charismatic, you know, authoritarian leader. You actually, the organization and the culture is so strong, what you want is someone who knows how to run the team. Yeah. Right? And who puts their institution first and their own ego and self…

AI assessment note: “it really depends on the nature of the leadership challenge.”

Q What is the difference between the two, and how do we know where we're sitting?

A Yeah. The term desirable difficulty refers to the notion that, um, uh, that some degree of constraint Um, or difficulty in learning is advantageous. That, um, being forced to adapt to some kind of difficult circumstance enhances the quality of speed and the quality of our learning. Now obviously, you know, the word desirable means that there's a distinction between an undesirable difficulty and a desirable difficulty. It is difficult to get a college education in a, you know, third world country. That doesn't mean you should get a college education in a third world country. That's not a desirable difficulty. A desirable difficulty would be Um, where I say to you, you know, ah, Maybe you go to, maybe you're in a classroom where there's, ah, there's more kids than normal, or maybe you've got a, ah, you got to wake up at six o'clock every morning because you're, because you have a part-time job, or you're playing a sport, and so you're forced to kind of organize your day and be disciplined, or those are desirable difficulties, right? I think that kind of, like, encourages you to be thoughtful and intentional in how you use your time, It's a desirable difficulty, and you see, when we give people too much freedom, they, very often, they don't, they get, they get lost in it, right? That's because there aren't enough Think, they're not butting up against enough, um, you know, athletes…

AI assessment note: “the word desirable means that there's a distinction between an undesirable difficulty and a desirable difficulty”

Q What about someone who's afraid of public backlash or people disliking them? What would you say to them?

A We're talking about two slightly different things here. In the first case, we're talking about feedback in a professional, I'm assuming in a professional context. Your colleagues say, Someone comes to you and says, your boss comes to you and says, can you redo this? Wasn't up to our standards. Or, here's a way you can make this much better. Or, I realize you don't know this. You need to know this before you can, that's one kind of, that's private feedback, right? You're not, the world's not, doesn't know that. And that's the thing that I feel strongly that you don't have any choice. You have to accept that, learn from that, grow with that, right? That's the condition of being an effective professional. Um, public stuff is different. And I, and public stuff is, it's not of the same quality. It's really uneven. Like, presumably the feedback you get from your colleagues and your boss, in most cases, pretty high level, right? Unless you have a terrible boss. But the public stuff is all over the map. Some of it is bullshit. Most of it, in fact, is bullshit. It's people who don't know what they're talking about or whatever. And there's little bits here and there that are, as I said, of really high quality and you should pay attention to. But, and If it, when it's public, it is really, really easy to feel, to get shamed, or to get overwhelmed, or to feel, um, and that's, that's how, t…

AI assessment note: “if you are someone who can't deal with that kind of public stuff, then you need to be in a field”

Q Why do you think so many people think that, then? That's like, it was easier for our parents, everything was better, it's harder now for us.

A Well, I think they're talking about something different, that is it, was it easier to have a kind of stable middle class life in the sixties? Yeah, if you were a Educate a white person. Sure. Uh, so like, we, we have very selective memory of these things. It was easier to buy a house if you had a middle-class job in the sixties, but then You know, the house is a lot smaller than the houses we have now. So I don't know, I, I, I tend to be, the housing thing is a whole separate conversation, which I'm sort of mildly obsessed with, but, um, you know, we have, as a society, failed in some ways to, to, um, uh, to create markets for things we need. Housing being the perfect example. Not, not in Austin, but in other places in the country. But, um, in general, I'm not a, Pessimist about the day, the moment we live in. I think it is, it's, you know, particularly once you abstract out from the United States, I mean, if we were having this conversation in Africa, we would not be bringing this up. We would be like, there's never been a better time, or South America, or any place that was historically, um, economically disadvantaged. It's way, way, way, way better now than it's ever been.

AI assessment note: “we have very selective memory of these things.”

Q time performing, and I can't ascertain their IQ, we don't do any sort of tests like that, but I might have some indications, and so I was curious, do you think that that applies as you get older? Like, we don't want to maybe make it a general rule, but as you get older, Does this rule in some ways hold? And is there any evidence to show us that?

A We're never in an environment that is as, um, clean and easy to kind of calibrate as we are when we're choosing colleges. We don't rank employers the way we rank colleges, right? You can't say that, you know, working for Yahoo is, you know, is different from working from Microsoft in the same way that, uh, East Tennessee State is different from MIT, right? There's not that kind of, so it's just a little trickier, but I do think You know, I just, I was thinking of this the other day. I have a friend named Nick, who's younger than me, but also, well, I'm a runner. He's just a, he's just on another level as a runner. He's actually, for his age, a world-class runner, and like, it doesn't do me any good to run with Nick, right? It's, it's, I can't keep up. He's slowing down for me. It's, what looks effortful for me is effortless for him. All it does is remind me that I'm a mediocre runner, right? Um, but I also, I can't even meaningfully be stretched by running from him, with him, because he's just too far ahead. I would be meaningfully stretched if I ran with someone who is a little bit better than me. That's where it gets, where I can actually, where they're going at 70%, and I'm, I can keep up if I go to 85%, so I'm actually getting a Better workout. That's actually, that makes a lot of sense. There's no scenario where I can keep up with Nick.

AI assessment note: “so it's just a little trickier, but I do think”