Michael: Alright Kevin, let's talk about that pro-con list you probably made for your last big decision. Kevin: Oh boy, you mean the sacred spreadsheet? The one where I weigh the future of my life in two columns? Of course. It’s the smart thing to do. Michael: Well, what if I told you it was probably a waste of time? In fact, it might have made your choice even harder. Kevin: Whoa, shots fired at my entire decision-making process! What do you have against organized, rational thought? Michael: Nothing at all, for certain kinds of problems. But today, we're exploring why the most rational-seeming tools are often useless for life's most important questions. We're diving into the book Wild Problems: A Guide to the Decisions That Define Us by Russ Roberts. Kevin: And what's so fascinating is that Roberts is an economist! He's the host of the famous EconTalk podcast. You'd expect him to be the king of cost-benefit analysis, but he's written an entire book arguing against it for the big stuff. Michael: Exactly. He's using his own discipline's tools to show us their limits. And that's our starting point: the fundamental difference between the problems a spreadsheet can solve, and the ones it can't. Roberts calls them "tame" versus "wild" problems. Kevin: Okay, I'm intrigued. Tame versus wild. What's the difference? Michael: A tame problem is like trying to find the fastest route from here to Chicago. There's a clear goal, you have data like traffic and road closures, and an algorithm—like the one in your GPS—can calculate the optimal solution. Making a random turn is a bad idea. Kevin: Right, you follow the map. Simple. Michael: But a wild problem is deciding whether to get married, or who to marry. Or whether to have children, or what career to pursue. There’s no data for how you will feel in ten years. There's no algorithm. And that’s where our most trusted tools begin to fail us, spectacularly.

Kevin: That makes sense. You can’t Google “Should I marry Sarah?” and get a definitive answer. But people still try to tame that problem, right? That’s where the pro-con list comes in. Michael: They do. And the book uses one of the most brilliant minds in history as the perfect case study: Charles Darwin. In 1838, he was grappling with whether to marry. And being the systematic scientist he was, he took out his journal, drew a line down the middle, and made a list. Kevin: I love this. What was on Darwin's list? I'm picturing things like "potential for genius offspring" on the pro side. Michael: You're not far off! On the "Marry" side, he listed "constant companion," "someone to take care of house," and charmingly, "charms of music & female chit-chat." But the "Not Marry" column was brutal. He wrote "terrible loss of time," "less money for books," "forced to visit relatives," and the fear that he'd become, in his words, "a fat, idle man." Kevin: Wow. That is a man who is clearly terrified of losing his focus. He's trying to run a cost-benefit analysis on love. Michael: He is! And this is the core of the issue with wild problems. The list-making approach assumes you can rationally weigh these things against each other. But how many points is "constant companion" worth? And how many points do you subtract for "visiting relatives"? It's an illusion of rationality. Kevin: So a 'wild problem' is any decision where you can't really know the outcome because the choice itself fundamentally changes you? Michael: Precisely. Roberts introduces a fantastic metaphor for this, borrowed from the philosopher L.A. Paul. It's called the "Vampire Problem." Kevin: The Vampire Problem? Okay, now you've really got my attention. Michael: The idea is this: imagine you're given the choice to become a vampire. You can try to make a pro-con list. Pro: you get to live forever, you're super strong. Con: you have to drink blood and can't go out in the sun. You can even interview other vampires, and they all tell you, "Oh, it's great, you'll love it!" Kevin: But you have no way of knowing if you'll like it. You, the human, might hate the idea of drinking blood. But the future you, the vampire, might find it delicious. Michael: Exactly! You cannot know what it's like to be a vampire until you become one. And once you do, your preferences, your values, your very identity is transformed. The person who made the decision no longer exists. That’s what having a child is like. That's what a major career change is like. The 'you' making the list isn't the 'you' who will live with the consequences. Kevin: That’s a perfect analogy. It's like trying to explain to my single friends what having a newborn is like. They can hear the words "no sleep," but they can't feel the reality of it, nor can they feel the overwhelming love that makes it bearable. Their current self can't compute the data of their future self. Michael: And that's what Darwin discovered. His list was full of negatives, but in the end, he scribbled a passionate rebuttal to his own logic. He wrote, "My God, it is intolerable to think of spending one’s whole life like a neuter bee, working, working, & nothing after all." And at the bottom of the "Marry" column, he just wrote: "Marry—Marry—Marry Q.E.D." It was a leap of faith, an emotional choice, not a calculation. The list didn't give him the answer; it just revealed his heart's deepest fears and desires. Kevin: So the list is a tool for self-discovery, not a calculator for the future. That’s a much better way to think about it. It helps you understand what you're afraid of, not what you should do. Michael: That's the key. The attempt to tame the wild problem with logic failed, but in failing, it revealed something much more important.

Kevin: Okay, so if the lists are out, and we can't trust our rational calculations for these big, life-altering decisions, what are we supposed to aim for? Just a gut feeling? A coin toss? Michael: This is where the book pivots from deconstruction to construction. Roberts argues we've been aiming at the wrong target. The modern world, especially in a data-driven sense, tells us to maximize "happiness" or "utility." Kevin: Which sounds reasonable. I mean, who doesn't want to be happy? Michael: But the book makes a powerful case that "happiness" is a cheap, fleeting goal. Instead, it proposes we aim for something the ancient Greeks called eudaimonia, which Roberts translates as "flourishing." Kevin: Hold on, eudaimonia? Can you break that down for us? It sounds like something you'd order at a fancy spa. Michael: It's a fantastic concept. It’s not just about feeling good. Flourishing is about living a life of purpose, meaning, virtue, and integrity. It's about becoming a certain kind of person. The book uses a classic philosophical thought experiment to draw the line: the choice between being a "satisfied pig" or a "dissatisfied Socrates." Kevin: A satisfied pig or a dissatisfied Socrates. I think I know which one I'd rather be at a dinner party with, but tell me more. Michael: The satisfied pig is perfectly happy. It has all the food and mud it could ever want. It experiences maximum pleasure, zero pain. Socrates, on the other hand, is full of questions, doubts, and struggles. He's often dissatisfied with the world and himself. The question is: whose life is better? Kevin: A pure utilitarian would say the pig's, right? Maximum pleasure, minimum pain. The math works out. Michael: Exactly. But John Stuart Mill, the philosopher, argued it is "better to be a human being dissatisfied than a pig satisfied." Because being human involves grappling with higher questions of meaning, purpose, and morality. Flourishing is the stuff of Socrates, not the pig. It's the sense of living a life that is rich and meaningful, even if it's difficult. Kevin: But isn't that a bit of an intellectual cop-out? Someone's having a miserable day and you say, 'Oh, you're not unhappy, you're just flourishing.' How is it actually different from just long-term happiness? Michael: It's a qualitative difference, not just a temporal one. Think about running a marathon. In the moment, at mile 20, your day-to-day happiness is probably at an all-time low. It's pure suffering. A narrow cost-benefit analysis would say, "Stop this immediately!" Kevin: Right, the "pleasure" score is a negative ten. Michael: But the overarching sense of accomplishment, of pushing your limits, of achieving a difficult goal—that contributes to your flourishing. It gives your life a story and a meaning that transcends the momentary pain. The book tells a great little story about a salesperson at a hiking store who asks a customer if they're planning a "Type 1" or "Type 2" experience. Kevin: Type 1 or Type 2? Michael: Type 1 fun is enjoyable while it's happening, like eating ice cream. Type 2 fun is miserable while it's happening but rewarding in retrospect, like a grueling mountain climb. Roberts argues that the most meaningful parts of life—marriage, parenthood, a challenging career—are often Type 2 experiences. They are what build a flourishing life. Kevin: I can see that. And this is where I think the mixed reviews of the book come from. It's a beautiful idea, but it's not a metric. You can't measure 'flourishing' on a scale of 1 to 10. It feels... slippery. It's not a concrete tool. Michael: That's exactly Roberts' point! He's saying we have to get comfortable with that slipperiness. The most important things in life are unmeasurable. The goal isn't to quantify them, but to privilege them. To recognize that your integrity, your sense of purpose, your character—these things are in a different category. They aren't just another item on the pro-con list; they're the framework that holds the list itself.

Kevin: Okay, so we're throwing out the spreadsheets and we're aiming for this profound, unmeasurable goal of 'flourishing.' This is all great philosophy, but what does it actually look like in practice? What does a person do on a Tuesday afternoon when they get a job offer that pays more but feels less meaningful? Michael: This leads directly to the book's final, and perhaps most poetic, piece of advice: you have to learn to live like an artist. Kevin: Live like an artist. That sounds great for a weekend retreat, but what does it mean for my career choice right now? Does it just mean 'be creative and see what happens'? Michael: It's more structured than that, but it's a different kind of structure. An artist, like a sculptor, doesn't start with a perfect blueprint. They start with a block of stone. They have a vague idea, but the final form emerges from the process of carving. They make a cut, step back, see what's revealed, and make the next cut based on that new information. Life, Roberts argues, is the same. It's an emergent process of discovery. Kevin: So my life plan should be less like an architect's blueprint and more like a jazz improvisation? That's both terrifying and liberating. Michael: It is! And to do it well, you need a different toolkit. Roberts offers a surprising role model here: Bill Belichick, the famously stoic head coach of the New England Patriots. Kevin: Bill Belichick? The guy in the hoodie? How is he an artist? Michael: It's about his strategy for the NFL draft. The draft is a classic wild problem. Teams spend millions scouting college players, but predicting who will succeed in the pros is notoriously difficult. So what does Belichick do? He often trades his high, "sure thing" draft picks for a larger number of lower picks. Kevin: He's trading quality for quantity. Michael: He's trading false certainty for optionality. He knows he can't predict perfectly, so he gives himself more chances to be right. He brings in a bunch of players, puts them in his system, and sees who actually thrives. He's not trying to guess the future from a distance; he's creating low-stakes experiments to reveal the future. And he's ruthless about cutting his losses. If a high draft pick isn't working out, he's gone. Sunk costs are sunk. Kevin: Okay, I see the connection now. So 'living like an artist' means creating options for yourself. Taking a job not because it's the 'perfect' final step, but because it opens up three other potential doors later on. It's about collecting experiences and skills, not just following a pre-set path. Michael: Exactly. It's about saying 'yes' to things that create serendipity. And it's also about being a great editor of your own life. In writing, they say you have to be willing to "kill your darlings"—to cut a beautiful sentence or a favorite character if it doesn't serve the story. In life, that means being willing to abandon a path or a dream you once loved if it's no longer contributing to your flourishing. Kevin: That’s hard. People cling to their past decisions because they don't want to admit they were 'wrong.' Michael: But the artist's mindset says there is no 'wrong.' There's only the work in progress. You are the sculpture, and you are also the sculptor. You are constantly refining, learning, and adapting. The goal isn't to arrive at a finished, perfect statue. The goal is the act of carving itself.

Kevin: So when we strip it all down, this book feels like a rebellion against our modern obsession with optimization. We want the perfect life hack, the perfect morning routine, the perfect decision-making algorithm to guarantee we don't make a mistake. Michael: And Russ Roberts, the economist of all people, is telling us that for the things that truly define us—love, purpose, family, identity—that entire search is a dead end. The frameworks that help us build a bridge or pick a stock are the wrong frameworks for building a life. Kevin: It's a profound shift in perspective. He’s not giving you a new map. He's telling you to throw the map away and learn to navigate by the stars. Michael: And to enjoy the journey of exploration! The point isn't to solve the mystery of your life. It's to live inside that mystery. To embrace the wildness, not try to tame it. The book ends with a beautiful quote from the final Calvin and Hobbes strip. Calvin is on his sled, looking out at a fresh blanket of snow, and he says, "It's a magical world, Hobbes, ol' buddy... Let's go exploring!" Kevin: That's a perfect way to put it. It leaves me with a big question, for myself and for our listeners: What 'wild problem' are you avoiding right now because you're stuck trying to find the 'right' answer before you even take the first step? Michael: A question worth sitting with. We'd love to hear your thoughts on this. Find us on our socials and share a wild problem you're grappling with, or a time you chose flourishing over simple happiness. Let's build a community around these big, important questions. Michael: This is Aibrary, signing off.