The Arithmetic of Uncertainty

Producer’s Note: This transcript was created using AI. Please excuse any errors.

Annie: So Barry, I’m so excited to be talking to you today, not just because your work has been something that I’ve been a huge fan of for a really long time. I’ve written about your work in my books, actually. But also just, like, historically, the number of intersections and overlap that we have in our lives. So Henry Gleitman and Lila Gleitman, his wife, Henry originally was teaching at Swarthmore before going to Penn. You got your PhD at Penn.

Barry: Yeah.

Annie: I did too. And we have so many people in common through those connections, uh, including John Barron. So-

Barry: No, it’s extraordinary. And somehow, although, you know, I went to Swarthmore, which is not very far from

Annie: Penn- Yeah …

Barry: I somehow never s- don’t think I ever saw you-

Annie: No

Barry: … when you were a graduate student. You know, I finished long before you started. I was done in ’71, but, you know, I was coming down there all the time. Maybe we were in the same audience and I didn’t know who you were-

Annie: Yeah

Barry: … and you didn’t know who I was.

Annie: I bet we were probably in that same colloquium room. Probably. That is my guess. So I just feel like there’s so much intertwining, and so I’m so glad to get to meet you. I know that quite a bit of your work has been on sort of the human drive to explain. So I’d love for you to kind of talk about that work a little bit and maybe give us an example of seeing that drive in action.

Barry: You know, people like to think that they get what they deserve and they deserve what they get.

Annie: Mm-hmm.

Barry: And that just is not true even in an ideal society, and let alone in an actual one.

Annie: Mm-hmm.

Barry: So the thing about explanation is that it takes the particular and it fits it into a more general framework, and without the general framework, you don’t know how to use the particular, this moment, to predict what’s gonna happen next.

Annie: Right.

Barry: Because you have to put things in the right categories in order to predict what’s gonna happen next, because it’s only gonna happen next if the next situation is similar in relevant ways to this one. But you don’t know what similar means unless you know how to categorize the world. And psychologists have, of course, studied this, cognitive psychologists, and worried about it, and social psychologists have studied how sort of the social context influences people to put things in correct categories often self-serving incorrect categories often. And the result is that the more fundamental issue, which is that you can’t live without explaining-

Annie: Mm-hmm …

Barry: sort of doesn’t get the attention it deserves, because psychologists are much more focused on the micro than they are on the macro.

Annie: Mm-hmm.

Barry: And you know, there, there’s a wonderful couple of articles that were written, uh, almost half a century ago by a cultural anthropologist named Robin Horton.

Annie: Mm-hmm.

Barry: His question was, how does the traditional form of explanation compare to scientific explanation? So he studied so-called primitive societies and compared them to modern industrial societies, and the conclusion he came to is that everything we aspire to do in our enlightened society, people who believed in gods, and omens, and stuff like that, they aspired to do exactly the same things. The one respect, you know, they wanted to explain the particular by appealing to something more general. They wanted to explain the particular so that they could predict the next particular. They had the same aspirations. They sought the same kind of generality. The one exception, he said, was the invention of the experiment.

Annie: Mm-hmm.

Barry: What science did is it said it is okay to create a world that is different from the actual world, and in that way, control factors and get a much better understanding of what’s going on. For the traditional society to control the world, to distort the world, is to make whatever you learn irrelevant to the actual world And so even if it had occurred to them to do experiments, they wouldn’t have done them because what, you know, what the hell does that tell you about the real world?

And there’s a sense in which the theme of the book, Choose Wisely, is that what this framework called rational choice theory has done is in effect invent a world that is so unlike the actual world when it comes to making decisions that you can’t use it as a model for how to go about living your life.

Because especially the important decisions, you can’t wedge them into a framework that rational choice requires where you know exactly what you value, you know exactly what the probability is of each of the outcomes that might occur, and then you just have to enter those data, push a button, and out comes the answer, what should I do tomorrow? What should I do with my life? That isn’t the world we live in, and rational choice theory pretends that it is or encourages us somehow to turn the world we live in into that kind of world.

Annie: Let’s just sort of step back a second just to get some definitions out here for people so you can have this conversation, ’cause I’m very excited to have this conversation. Let’s just start with if you could define rational choice theory and maybe give a little bit of a history from the… This is coming from economics obviously. Maybe give a little history from economics in terms of the, the evolution of, of rational choice theory.

Barry: Sure. I’ll try to keep it brief and simple. Rational choice theory assumes that the aim of any decision is to maximize utility-

Annie: Mm-hmm …

Barry: or to maximize preference. Now, they use those words utility and preference to acknowledge that people have different values. It has nothing to say about what values people should have. Preferences famously are, quote, “exogenous,” which means you come into a situation with your preferences already formed. And then you look at the options, ask, “How well will each of these options satisfy my preferences?” So you have to assign a value to each of the options. Where should I eat tomorrow night? Where should I go on vacation? Which job should I take? Who should I marry? Anything. How much value am I likely to attain from each of the options that are in front of me? So that’s piece one.

Annie: Mm-hmm.

Barry: Piece two, how certain am I that if I choose a given option, I will actually attain that value? In other words, the world is an uncertain place. You can make the right decision and it won’t work out. And so for every option, you’ve got a value, how good will it be, and a probability, how sure am I about how good it will be? You multiply those two together, you get an expected value or an expected utility, and your job is to choose the option that has the highest expected utility. That framework, which by the way, has a, a very close cousin in what’s called cost-benefit analysis, which is the way important policy decisions get made throughout the government and throughout business.

That’s the normative standard. And the work on decision-making that psychologists have done, starting with Kahneman and Tversky half a century ago- Has focused on how bad that model is as a description of how people actually choose

Annie: Mm-hmm

Barry: Never have they addressed whether it’s good or bad as a norm, as a standard. The assumption has been, this is the right standard, when and how do people deviate from the standard? Our book is su- a suggestion that it’s not the right standard.

Annie: So, l- so let’s try to just ground this for a second in a situation. So I think that from my standpoint, rational choice theory is easier to understand if you kind of put yourself in a situation of omniscience. And I think this is one of the things you’re saying, where I actually know what the payoff is, and the payoff could be measured in anything that’s gonna advance you toward your goals in alignment with your values. So when we’re talking about utility, we’re saying, “How much is this gonna get me to the thing that I desire?”

Barry: Right.

Annie: And let’s assume that we know exactly what that payoff is, what that gain is gonna be, and we know the probability of achieving it.

Barry: An alternative I have come to call radical uncertainty, and that’s a situation where you can’t attach probabilities to outcomes. You’re trying to decide what job to take, and you care about advancement, how interesting is the work, um, how good will your colleagues be, what is it like to live in this part of the world, et cetera, et cetera. You can’t attach probabilities to your assessments. Suppose you are really attracted to the colleagues you met, but half of them leave and start their own companies. Can you attach a probability to that? No, you can’t. There’s a kind of uncertainty that can’t be quantified, and that’s what people hate.

Annie: It’s very rare that we know nothing. Right? That would, that would be a very rare-

Barry: Mm-hmm.

Annie: … thing. So, you know, I do this exercise with people where I say, “What’s the weight of my dog?” They’ve n- they have no picture of my dog, they haven’t seen my dog, right? So obviously we’re in, they don’t know, right? They have no idea. And very… You know, often they’ll just say, “Well, I don’t know. I’ve never seen your dog.” I say, “Great. Okay, fine. Can you tell me what your best guess is?” And they’ll give me their best guess, and it’s usually somewhere between, like, 25 and 40 pounds. So let’s say they guess 35 pounds. I say, “Great. Okay. What’s the smallest amount that you think my dog can weigh?” And they’ll usually say, like, 10 pounds. And I’ll say, “Okay, what’s the heaviest that you think my dog is?” And they’ll usually say 120 pounds. Okay, so what… This is very uncertain, right? Like, they’re telling me, like, point estimate is 35, lower bound 10, upper bound 120.

And I say to them, “Oh, okay, that’s interesting. Why didn’t you say 500 pounds?” And they say, “Well, ’cause dogs don’t weigh that much.” And I say, “Oh, so you know a lot about what my dog weighs, actually.” And then I say, “Well, 35 is a lot closer to 10 than it is to 120. So why was your best guess so close to 10?” And they’ll say, “Well, like, smaller dogs are more… There’s more of those in the world, and there’s fewer really big dogs in the world.” So you’re telling me, like, the distribution is skewed. That’s really interesting, right? So the reason why I bring this up is that I feel like there’s use in sort of trying to figure out, well, what are the things that I do know, and what are the things that I don’t know? And even if there’s a whole lot I don’t know, trying to sort of figure out, well, what are the things I do know is actually, like, a useful exercise.

Barry: Yep. It absolutely does have enormous value, and you’re right that there are really almost no situations where we’re completely ignorant. But if, uh, you were to ask me, well, how come you were operating within these constraints- I wouldn’t know how to answer you because I wouldn’t have thought about it, you know?

Annie: Right. Right.

Barry: I would just generate some numbers thinking they came from nothing, and you would, over time, you’d get me to see that I actually know a lot more about your dog than I thought, because I know a lot more about dogs than I-

Annie: Right.

Barry: … thought, ’cause I’ve never really thought about it. So it’s important to encourage people to ask whether they might know things that they don’t think they know, if they frame the problem in a way that allows the knowledge they have to come to bear on their estimate. But the thing about assessing value that I think is deeply problematic, underappreciated, is that there isn’t a common scale of value. When you’re deciding what job to take, what’s the scale that you use to array how good is the salary, how good is the opportunity for advancement, how good is the community to live in, what are my colleagues gonna be like, how interesting is the work? If you’re gonna do it, quote, “right,” you create a spreadsheet and you assign a value to each of these things, let’s say on a 10-point scale. Is a 10 in colleagues and a 10 in salary the same 10? If it isn’t the same 10, then you can’t do the Excel analysis.

Annie: Right.

Barry: But why on earth would anyone think it’s the same 10? And again, what rational choice theory forces you to do is operate as if there is a single scale of value, and any decision you make, all of the attributes of the decision can be given a value on that scale. Now, we have a model for that. We call it money. The thing about money is it has exactly those properties. But life is not just money. And when you, when you wedge people into a much narrower frame than what real life gives them, they invent numbers because that’s what Excel demands of them, and then they act as if the numbers they’ve invented are real. And so there is this worship of being able to quantify without much concern about whether the quantification is actually capturing reality in a way that matters. And we know from lots of research that whichever feature of a decision is the most quantified is the feature that people will put the most emphasis on.

Annie: Right.

Barry: Because it seems more objective.

Annie: Right.

Barry: And the more objective it is, the better. And so things that are not very important loom larger if you can attach a number to them. And one of the main points of the book is to suggest th- that this almost certainly, in the kinds of decisions we actually face in life, will lead to terrible decisions. You know, it substitutes counting for thinking.

Annie: Mm-hmm.

Barry: And you, you have to think as, for example, what do I know about dogs?

Annie: Right.

Barry: That’s an unbounded question. Some of us will extract more that we know than others of us, if we think about it hard enough. And anything that wedges us into a framework that is more narrow than the one we should be using is not doing us a favor, and that’s why I think it’s such a problem.

Annie: I think this is part of the problem, right? Is that when people look at something like rational choice theory, I think they take it as an equation that has a right answer. And I think you have to kind of throw that idea out, the right answer part, and say, “Look, it’s giving you a sense of how you might think through a problem, but that you have to lose the idea that you have a right answer,” right? You have to realize it’s completely dependent on what your values are. It’s completely dependent on what your goals are.

You yourself have to figure out how much do I care about those different things. And then, and I think this is one of the most important points, you have to know that not only is it gonna be so far from right that it’s hilarious, right? And accept that, but you have to be willing to say, “When I get new information, I have to keep changing my mind over and over again, and my actions need to map on that.” And I think that that’s where people really go wrong.

Barry: I think you’re right. The huge problem, uh, with that, with the updating issue, I think, is captured in the decision-making research, uh, with, uh, what’s called anchoring and adjustment.

Annie: Yeah.

Barry: So people realize they have to update. But they don’t update enough because they’re anchored with their initial set of beliefs. So I think that’s absolutely right, and updating is crucial, and we need to at least consider the possibility that, like a Etch A Sketch, we gotta erase everything and start again from scratch. You know, you say you have to know what your values are, but your values can change, and your values may not be comparable across the board. You know, the thing about using rational choice theory that we suggest in the book is that it’s great to create a spreadsheet because it’s really good to scrutinize your decision and ask yourself, as you put it, “What do I care about, and how much do I care about it?”

Annie: I wanna push back on this a tiny bit. So I agree, like please create the spreadsheet in terms of here are the things that matter, right, for this decision. I want colleagues I like. Maybe you wanna make a lot of money. I don’t know. Maybe you don’t. Maybe you don’t care. I wanna make enough to be able to fund my leisure time, whatever it might be. I wanna feel, feel fulfilled in my work.

Barry: Yep.

Annie: Not everybody wants that, right? I want my work to be my passion. That’s one of my pet peeves. Why we assume that should be true for everybody, right? Which is, I think, another problem, particularly in this social media world, is that people impose their values on other people. Which is, I think, one of the reasons why it’s really good to create what the spreadsheet’s gonna be. Like, here are the things that matter to me, because I think that we think our work is supposed to be our passion, but maybe it’s not. Maybe rock climbing is your passion and work funds rock climbing. I don’t know, right? Like, you should… That’s why we should be-

Barry: Well, no, and this is a huge problem because young people really somehow have swallowed the Kool-Aid, and if they haven’t found the passion, they think there’s something wrong with them.

Annie: Exactly.

Barry: You know? Not, not only are we supposed to be pursuing our passion, but we should know what that is when we’re the ripe old age of 19.

Annie: Exactly.

Barry: So it puts enormous pressure on young people that is unjustified, and as you point out, their elders don’t realize that they’re imposing their values. You know, I’ve had people say, “Listen, other aspects of my life are more important than how I make a living. I don’t want to bring work home with me at the end of the day.”

Annie: Right.

Barry: Yes, I wanna live a nice, comfortable middle class life, but I want to make sure that it doesn’t crowd out the other things in my life that I care much more about, like my family, the community, the political work, the rock climbing, you name it. And that seems like Oh, you don’t understand. You know, you spend half your waking life working. It’s gotta be your passion. Excuse me. No, it doesn’t. We don’t appreciate that we’re imposing our values on other people. On the other hand, we want to encourage other people, as you clearly are doing, to scrutinize their values.

Annie: Mm-hmm.

Barry: To interrogate their values, to challenge their values. But what worries me is that I think, yes, it’s often the case that we can’t know until after we take a shot and discover that it was the wrong shot, but I think we can know more than we do if we actually ask ourselves these questions.

Annie: 100%.

Barry: You know, in real life, when people are deciding where to go to college, they go to U.S. News and World Report, and U.S. News and World Report puts value on things that can be quantified.

Annie: Right.

Barry: What’s the size of the school’s endowment? Now, that’s related to the quality of education, but is it perfectly related to the quality of education? Obviously not. What’s the average course evaluation that students give to their teachers? That’s related to the quality of instruction. Is it perfectly related? Of course not. And the non-quantifiable aspects of the decision about where to go to college disappear because it looks like everything can be quantified, and then you push a button, and you get the ranking.

Now, if people weren’t slavishly driven by that, I wouldn’t worry so much, but they are. And there’s an example in the book that illustrates how dangerous this can be. It’s only for old people, this example, but it… back in the horrible days of the Vietnam War, it was a very unpopular war, and because it was what’s called an asymmetric war, it was very hard to know who was winning. And so the people in power in the U.S. cared a lot about having popular support for the war, and somebody came up with the idea that we needed a metric so that citizens of the U.S. would know whether w- at least we were winning. And the idea was that if we’re winning, people will be less opposed than if we’re not.

So how do you assess whether you’re winning in a war like that? Well, they decided a good, a good proxy would be body counts The more casualties you extract, the more, the better you must be doing. And that became the measure of how well the war was going. Is it an imperfect? Sure it is. So far, not the worst thing in the world. What made it the worst thing in the world is that it led people to change strategy to maximize body counts, because that was the proxy that was gonna sell the war to the public. So that’s what we’re going to achieve, and let’s just hope that’s a good enough proxy that if we maximize casualties, we’ll also be making progress in the war. This is not a trivial mistake. This is a mistake that cost thousands of lives.

Annie: Yeah. So I completely agree with you, right? Like, this perversion of metrics, I totally agree with you. I think it’s partly a failure in the way that we educate. I think it’s a failure to think these things through, like what are the unintended consequences of the metric.

That being said, I think that if you educate people in the right way, in the same way that you’re talking about, right, which is like, let’s actually interrogate our values. Let’s try to figure out what those things are, and you get people to hold these things loosely, that making that your best guess of the quantification would be explicit, I do think has value.

Barry: Yep.

Annie: Right? I feel like people live in only two spaces, right? One is, “I couldn’t possibly know, so I’m not, I’m not gonna try. I’m just gonna wing it,” which Choose Wisely is trying to get people not to do, right? Just, just because you have no idea doesn’t mean you should wing it. You still have to explore, like, what are the things I care about, must be really thoughtful about those decisions. Or they think they should know, and now they’re analyzing, analyzing, analyzing, and maybe they’re getting into paralysis over that, and it generally is gonna make them unhappier, and it might not even be a decision that deserves the time. And that we need to get people in an in-between space between thinking that decisions are two plus two equals four, which is insane, what a nutty thing to think in the conditions in which we have to think, and thinking, “I’m just gonna wing it,” right?

And let’s move everybody somewhere in between those two things. And then the question of how much time you’re taking on the decision is independent of whether you feel like you should know the answer or not, and it has more to do with, look, what’s the long-term impact of the decision? Is this a situation where I can, like, s- be a super satisficer, like good enough is like a really low bar, or is this a situation where good enough should be a higher bar?

Barry: Yep. You get to make a different mistake tomorrow. That’s exactly right. But, you know, again, the vision that this aspiration to quantify creates in people is that they should know.

Annie: Right. Right.

Barry: And if that’s what you think, then you’re gonna beat yourself up any time something goes wrong. The information was out there and you didn’t take advantage of, or you didn’t calculate it right, or you don’t know yourself right. You know Dan Gilbert, whose work I assume you know, he makes the point that I think people really should have tattooed on their arms, that every decision is a prediction

Annie: Mm-hmm.

Barry: And we know ourselves, but not nearly as well as we think we know ourselves, so the prediction that we are making can be wrong. It can be wrong because the world is uncertain, and it can be wrong because we are uncertain. And we appreciate neither the uncertainty of the world nor our own uncertainty about ourselves enough to appreciate how often we can do everything as right as we are capable of and still end up dissatisfied with what we’ve chosen. And as we discovered earlier in our conversation, this kind of uncertainty is something people find intolerable. It’s bad enough that you can’t count on a particular result. It’s worse that you can’t explain why that particular result happened. You don’t know what, if anything, to do differently the next time. And the, you know, the ch- the challenge of appreciating, A, that every decision is a prediction, and B, that the prediction depends on knowing yourself partly, creates, you know, it’s like, how can I not know myself? What’s wrong with me?

Annie: Right. Nobody will accept that.

Barry: Uh, when I retired from Swarthmore, they gave me this lovely day to celebrate my career there, and I gave a talk, and the point of my talk was to illustrate how much the path of my career depended on luck.

Annie: Mm-hmm.

Barry: Which is not to say that I did not take advantage of the opportunities. I was more than willing to pat myself on the back. But the biggest factors in my trajectory, I didn’t choose. They were imposed on me. I happened to meet my wife in junior high school. If my family’s business had been a little bit more successful, we would have moved into a different neighborhood, and my wife’s and my paths would never have crossed. Do I pat myself on the back for meeting my wife? No. I pat myself on the back for at least recognizing that I’d met something, someone wonderful, you know? I had a s- introductory psychology when I didn’t even know what the field was, taught by a guy named Philip Zimbardo, who was generally regarded as the best introductory psychology teacher who ever lived, although Henry Gleitman would probably not agree.

Annie: Henry Gleitman would definitely not agree.

Barry: And I just became completely in love with psychology. I didn’t know what, still didn’t know what psychology was. I knew that I was in love with the psychology that Philip Zimbardo presented. You know, if someone else had taught that class, I probably would’ve been a history major. I don’t know what I would’ve been. So I take credit for doing well in psychology and for trusting my reaction. I don’t take credit for being in that position. That was just luck. And people hate the idea that luck plays the kind of role that it does.

I used to tell students at, at Swarthmore that whether they get into the medical school or law school of their choice is a coin flip. It’s not that they don’t deserve it, but 10 times as many people deserve it as are gonna get in. The people in the law school are pretending that they can actually distinguish among essentially equivalent applicants, but they can’t. So acknowledge that you have a 10% chance of getting into Harvard Law School, and it’s really just what gets picked out of the hat and not what you’ve done.

What you’ve done gets you into the set of possible candidates. It does not get you the position, and everyone pretends that there’s a kind of certainty to the evaluation and to the achievement that should guarantee you a particular path going forward. And I c- you know, it’s not like people disagree with me when I tell this to them, but they hate the idea that their future is a roll of the dice.

Annie: I say this all the time. There’s only two things that determine how your life turns out, luck and the quality of your decisions. That’s it.

Barry: Yep.

Annie: And don’t downplay the role of luck. It really matters. Now-

Barry: Right.

Annie: … the thing you have control over between those two things is the quality of your decisions, and you ought to be really focusing on that. But I make the point of like, what if Bill Gates had been or- born 40 years earlier or 40 years later? Does he end up Bill Gates? I think not.

Barry: Or born to different parents.

Annie: Or born to different parents, but this is where people, I think, really have trouble. I say, “But let’s take Bill Gates, born in the exact same circumstances that he was at the exact same time, and you run it 1,000 times.” How many times does he end up Bill Gates? ‘Cause it’s not 1,000.

Barry: Sure as hell isn’t.

Annie: It’s not even close to 1,000, right? And I think that people have trouble with that idea of, like, what is the influence of luck on your life? So I love that this was kind of your closing message to people, is it’s okay to take credit for recognizing opportunity, making better decisions than not so that you can increase where you land on the distribution of outcomes that might be available to you, right? You can sort of get out to that right tail at a higher probability. But that, of course, it’s the intersection of luck and skill. What else could it be?

Barry: Well, people think it’s just skill.

Annie: Yes.

Barry: I once published a piece in The Chronicle of Higher Education that suggested that college admissions should be done with a binary decision, the sorting, good enough to be successful, not good enough, and after that, a lottery.

Annie: Yeah.

Barry: And people thought I had lost my mind. How could something that important be decided by a lottery? And my response was, “Well, it already is decided by a lottery, but we pretend that it’s not.” But the push to quantify which rational choice theory encourages is, I think, a push against acknowledging how much is not quantifiable.

Annie: Yeah. Like, we can tell this person has good enough grades, the teacher references are fine, their LSAT above the bar that we would be good with. They have the r- you know, whatever. They worked at the White House, you know, whatever it is, right? Okay.

Barry: Yeah.

Annie: So they’re in the group of people that we think would do well. And then after that, it is a lottery. You’re completely tricking yourself into thinking that your ability to predict person A versus person B, and somehow figure out that person A has a higher probability of success at the school than person B does, that’s hilarious, right?

Barry: But people who should know better do it.

Annie: I know. I’m, I, I completely agree with you.

Barry: People making graduate Ph.D. student decisions in psych departments act as if it isn’t a lottery.

Annie: So I think about how much time are you supposed to spend on a decision with two very big ideas. One is, what’s the long-term impact of introducing error into the decision? Now, short-term impact, I try and get people away from because when you get the food in the restaurant and you don’t like it that much, you’re very sad. But if I talk to you in a month and I say, “Hey, you got like a, you know, a hamburger that was kind of mid. How much did it affect your happiness over the course of the month?” Your answer is gonna be like, “What are you talking about? Not at all.” Right? So long-term impact, does it have any long-term impact to make a slightly suboptimal decision compared to omniscience, right? Like, or a very suboptimal decision compared to omniscience. And then the other one, which goes back to that, you know, a lot of what this conversation has been, is how easy is it to reverse and are you gonna do it?

‘Cause if you can change it really easily, and this is something that I say to people when I’m, people come to me like asking about applying to college. I’m like, “You can transfer.” Is there a cost to transferring? Yes, there is. Sometimes you can’t take all your credits with you. You gotta restart your social life. Like, there’s definitely a cost to it. You know, it’s a bigger decision than a lot of things that you could do. But you can actually transfer, and nobody takes that into account when they’re actually applying to colleges. They don’t think about the fact that they can transfer, that if they don’t like it, if their prediction, a la Dan Gilbert, is it turns out not to be great, that they can actually transfer.

So if we take those two things into account, then what I say is we should all live in the world of am I dating or am I marrying? That’s all that we should be thinking about. Is this a, is this a date, or am I marrying somebody? And that should be determined, like, what is my bar for getting to the picking part?

Barry: Our criticism of rational choice theory is that we think it contributes to shutting down the reflection on values that needs to occur. There are two ways to make a decision. Either you do a spreadsheet or you go with your gut, and we think those are both deeply defective. You do not rely on a spreadsheet, and you do not go with your gut. You go with the product of your thinking, talking, reflecting, scrutinizing yourself, running it by other people, all of these things to help you clarify why you’re making this decision and why it matters.

Annie: One of the most useful things, I think, for increasing the quality of one’s decisions is disagreement, right? Like, I really want, within a group, within the people that I’m recruiting into a decision, to see a lot of dispersion. I think it’s really important. So a lot of how I think about the quantification piece, ri- like, let’s fill in those numbers, is actually to expose dispersion. So I kinda say two things. Like, if you want to find out what somebody else really thinks and be able to see disagreement, you need two things. One is you need to get their information without them knowing what you think, right? So if I’m gonna get your true opinion, you need to not know what my opinion is. Very, very important. But the other thing is I need to be able to see the disagreement. So I actually think about the quantification as a tool for exposing that we have a different point of view.

Now, to your point about, well, what does an eight mean? It may be that I put down an eight and you put down a two, and then we look at our rationalizations and it just turns out that we have different scales. I think that’s incredibly-

Barry: Yep.

Annie: … important to understand, right? So it helps us with that scaling problem. I think that it also is just-

Barry: As long as you talk about it rather than just averaging.

Annie: Well, that’s why you have to have the rationalization, and that’s why you h- you know, here’s my rationale, right? Here’s three to five sentences as to why I’m saying it’s an eight. Here’s three to five sentences. This is why I’m saying it’s a two. Sometimes we find out that we’re on different scales

Barry: And we realize, no, we’re just using the scale differently.

Annie: Right.

Barry: We actually agree, or no, we’re, we’re, we’re miles apart.

Annie: No, we actually are very far apart, and let’s have a discussion about that.

Barry: I think that’s helpful.

Annie: And, but here is the key. With no intention that you’re gonna agree in the end, and understanding that averaging those two numbers together makes no sense.

Barry: Well, that’s a v- those are big qualifications.

Annie: Right.

Barry: My version of this, a point I make when I give talks about the paradox of choice, is when Trump was running against Hillary Clinton. There are two options, and when people choose Hillary Clinton, how much do you know about them and their politics? Not very much. There are a million reasons you could make that choice. Compare that to the primaries where there were 20 Democratic candidates.

Annie: Mm-hmm.

Barry: Now, if somebody chooses Hil- Hillary Clinton, that tells you a lot more.

Annie: Right.

Barry: Because you’ve got this whole continuum of people, and choosing Hillary Clinton really articulates the values that you have and your expectations in a way that choosing Hillary Clinton in the general election doesn’t. It’s a consequential choice. It says something about you that you vote for Hillary Clinton rather than for Donald Trump, but not nearly as much as it says about you when you choose Hillary Clinton from a set of 20 alternatives. And that’s why one of the arguments that I make with collaborators is that when the set of options is large, the choices you make say something to you and the world about who you are.

Annie: Mm-hmm.

Barry: Whereas when the choice set is small, Lee’s or Levi’s, the choice doesn’t say much about who you are, because human diversity is so much greater than two sets of jeans to choose from. So in a diverse world where people talk to one another and scrutinize themselves, quantifying is helpful. In a homogeneous world or a world in which decisions are made in isolation, it may be harmful. And the question is, what world do we live in? And that sort of depends on where you’re operating. If you’re talking to a group of people who work at the same company and work together, the structure is there.

Annie: Mm-hmm.

Barry: And your job is just to get them to take advantage of it.

Annie: Right.

Barry: But that’s often not the case, you know? It’s often that you’re on your own, largely. And again, if I don’t know myself, this is another thing people don’t like, that other people might know you better than you know yourself.

Annie: That is so true.

Barry: But, I mean, how demeaning is it that you have to ask your spouse, “What do I think? What do I think about this?”

Annie: What am I gonna like the best on this menu?

Barry: What am I gonna like the best on this menu? Yeah. Who am I gonna… Who should I… Who, who am I gonna vote for? I mean, you pick your problem. But, you know, I think when you’ve been together with somebody for a long time, it’s a reasonable bet that that person knows aspects of you better than you do.

Annie: I think that’s true.

Barry: But it’s not something that people find easy to accept, you know?

Annie: Yeah. All right, well, I think this is a wonderful place to leave it, ’cause we found out that we mostly agree.

Barry: We found out that we mostly agree.

Annie: We mostly agree, and we little, a little bit disagree, but it’s actually more of a, like, what is the purpose? How are people gonna accept it? So, which is, I thought we were gonna end up.

Barry: I think in an ideal world where we could specify how a decision should proceed, we would agree.

Annie: Yes.

Barry: And the question is, how close does the actual world- Come to, yeah … come to being this ideal world? And that’s where we may disagree.

Annie: Well, I agree with you about that. Okay, so we just close with a couple of things. This has been such a lovely conversation. Thank you so much. So we always ask our guests, what do you think the impact on society will be when the Alliance succeeds in its mission to ensure Decision Education is part of every K through 12 student’s learning experience?

Barry: I think that people will make much better decisions, and the consequence of that will be that society will find meeting ground much more than it currently does. So, you know, I think that teaching people how to make decisions and teaching people how to think about uncertainty are at least as important as teaching them how to read, add, and subtract, and I only wish that you succeed in this mission.

Annie: Thank you. I, and I, I would argue more important than teaching kids trigonometry.

Barry: Certainly, or calculus.

Annie: Or calculus. They can learn that, you know, as an elective. Okay, if listeners want to go online and learn more about your work-

Barry: They can’t …

Annie: They can’t.

Barry: I don’t do social media. If they Google me, they’ll get all kinds of links, but I’m an old man.

Annie: Well, fair. Although, they can certainly go find your books online.

Barry: And they can go to TED. I’ve given a bunch of TED Talks.

Annie: I personally really enjoyed… I love Laurie Santos. Love the podcast that you did with Laurie Santos.

Barry: Yeah.

Annie: So definitely go check those things out. Anything that we’ve talked about in the show, particularly just now, is gonna be linked in the show notes-

Barry: Thank you

Annie: for this, so that people will be able to go and find those resources for you. Thank you so much for this great conversation. I am so excited about how deep we got to go. I learned a lot from this. I love being challenged, and I’m so grateful that you came on and had this conversation with me.

Barry: I feel exactly the same way. I’m incredibly grateful that you saw fit to have me on. I’ve been an admirer from afar despite the overlap in our past. This is the first time that I’m knowingly seeing you face to face, and it was a great conversation.

Published September 2, 2026