Wild Problems

Wild Problems Plot Summary

Introduction

Life presents us with decisions that cannot be solved by formulas or algorithms. These "wild problems" - like whether to marry, have children, or change careers - resist measurement and predictability. Traditional approaches to decision-making rely on balancing costs and benefits, attempting to maximize utility or happiness. Yet for life's most consequential choices, this framework falls short. Wild problems involve fundamental uncertainty, identity transformation, and questions of meaning that extend beyond simple pleasure and pain calculations. When we make a significant life choice, we not only experience new outcomes, but we become different people. Rationality, in its conventional sense, struggles when our very preferences and values might change as a result of our decisions. This book challenges us to reconsider how we approach life's biggest decisions, suggesting that flourishing - living a life of meaning, purpose, and integrity - matters more than momentary happiness. By exploring alternative decision frameworks and examining how remarkable thinkers have approached wild problems, we discover that embracing uncertainty rather than fighting it may be the wiser path toward a life well lived.

Chapter 1: Wild vs. Tame Problems: Understanding Decision-Making Limitations

Life presents us with two fundamentally different types of problems. Tame problems have clear goals that can be objectively assessed: finding the fastest route to Chicago, following a recipe to make the perfect omelet, or solving a chess puzzle. For these challenges, we can develop techniques that work reliably and produce predictable outcomes. When we apply rationality, science, and algorithms to tame problems, we see steady progress. Wild problems, by contrast, resist this kind of methodical approach. Should you marry? Who should you marry? Should you have children? What career should you pursue? These questions have subjective goals that are difficult to measure. There's no manual, road map, or algorithm that guarantees success. What worked for someone else might not work for you, and what worked for you yesterday might not work tomorrow. For most of human history, wild problems were "tamed" by authority and tradition. Kings, parents, religion, and cultural norms provided guidance on life's big decisions. But modern society has largely rejected these constraints. What was once destiny is now a decision - glorious in its freedom but challenging in its uncertainty. Without recipes to follow, we must navigate this landscape of choice in new ways. Our natural response is to try converting wild problems into tame ones. We gather data, make lists of pros and cons, and attempt to quantify what cannot be measured. This approach feels like progress, but it's often like searching for lost keys under a streetlight simply because the light is better there, even when our keys lie elsewhere in the darkness. By focusing exclusively on what we can measure or imagine, we ignore aspects of life that may be crucial but resistant to calculation. When we face wild problems, traditional rationality tools may lead us astray. The challenge isn't just about making better decisions - it's about understanding that for many of life's most important choices, there may be no objectively "right" decision in the way we usually think about it. Instead, we need a philosophy for facing uncertainty that acknowledges the limits of our predictive abilities and recognizes that who we become matters as much as what we experience.

Chapter 2: The Darkness of Uncertainty: Why Data Cannot Illuminate Life's Big Decisions

Charles Darwin, facing the question of whether to marry, created a list of pros and cons in his journal. On the "marry" side, he noted companionship, children, and someone to care for him in old age. On the "not marry" side, he worried about loss of freedom, less time for reading and work, and potentially having to leave London. This approach seems rational - weigh expected well-being from one choice against another, and choose the option with the highest expected utility. However, Darwin's list reveals the fundamental darkness surrounding wild problems. First, he cannot truly imagine what married life would entail, particularly its benefits. His list reflects what a single man might observe from the outside - focused on practical considerations like housekeeping and "female chit-chat" rather than the profound ways marriage might transform his identity and experience. The asymmetry of knowledge is striking - we can more easily imagine the constraints of marriage than its unexpected joys. Second, Darwin faces what philosopher L.A. Paul calls the "vampire problem." Before becoming a vampire, you cannot know what it will be like to subsist on blood and sleep in coffins. More importantly, becoming a vampire changes your preferences and values. Similarly, many life decisions involve crossing into experiences that will transform not just what we do but who we are and what we care about. The person making the decision isn't the same as the person who will live with its consequences. Third, Darwin's list reveals nothing about how marriage might affect his sense of purpose, meaning, and identity - elements that transcend day-to-day pleasures and pains. His consideration of marriage treats it as a series of experiences rather than a potential transformation of self. When we face wild problems, we cannot fully anticipate how our choices will shape who we become. The darkness surrounding wild problems isn't merely about insufficient information. It's about the impossibility of knowing certain things in advance. No amount of research can fully prepare you for what it's like to be a parent or to change careers dramatically. What makes these decisions wild is that some aspects of them can only be known through experience. When faced with such uncertainty, making lists of pros and cons may provide comfort, but it creates the illusion of control rather than genuine clarity.

Chapter 3: Beyond Utility: Flourishing Matters More Than Happiness

When confronting life's big decisions, many of us instinctively adopt what philosophers call utilitarianism - the view that right actions maximize pleasure and minimize pain. This approach, pioneered by Jeremy Bentham, suggests that when faced with choices, we should calculate which option produces the most "utility" - benefit, advantage, pleasure, good, or happiness. Economists have embraced this framework, viewing life as something like a day at an amusement park where we rationally seek to maximize satisfaction given our constraints. But many who have faced wild problems report something curious. When Persi Diaconis, a Stanford mathematician specializing in probability, was deciding whether to move to Harvard, a friend suggested he make a list of costs and benefits. Diaconis blurted out, "Come on, Sandy, this is serious." Similarly, psychologist Phoebe Ellsworth admitted that when making her own university-change decision, she abandoned her cost-benefit analysis when it wasn't "coming out right." These reactions suggest that something beyond narrow utility calculations matters deeply. Human beings care about more than day-to-day pleasures and pains. We want purpose. We want meaning. We want to belong to something larger than ourselves. We aspire. We want to matter. These overarching sensations define who we are and how we see ourselves. The Greeks called this condition eudaemonia, often translated as "flourishing" - living life fully by fulfilling our human potential with integrity, virtue, purpose, dignity, and autonomy. John Stuart Mill captured this distinction when he wrote, "It is better to be a human being dissatisfied than a pig satisfied; better to be Socrates dissatisfied than a fool satisfied." While psychologist Dan Gilbert argues that all that matters is our experienced happiness, this view misses how we care about more than just the sum of momentary feelings. A life of fifty years of pleasure followed by twenty years of regret differs profoundly from twenty years of suffering followed by fifty years of contentment. Flourishing is both quantitatively and qualitatively different from our day-to-day pleasures and pains. It persists and overlays our daily experiences rather than coming and going like momentary sensations. Our essence is not easily compared to our day-to-day feelings. Purpose, meaning, dignity, being a spouse or parent - these aspects define us and suffuse all our days, not just individual moments. They transcend and elevate our experiences, changing not just what we feel but who we are. This explains why many people willingly choose paths that bring more pain than pleasure - why people write haiku, join the army during wartime, run marathons, or volunteer without pay. Pain, especially when in service of an ideal, can be a source of meaning. That doesn't make us irrational. It often makes us admirable.

Chapter 4: Privileging Principles: Placing Values Above Cost-Benefit Analysis

When faced with ethical dilemmas, we encounter situations where our deeper principles clash with narrow self-interest. Imagine finding a wallet containing cash, credit cards, and identification. With no witnesses around, a purely utilitarian calculation might suggest keeping the money brings more personal benefit than returning it. Yet many people would return the wallet despite the apparent sacrifice of utility. This scenario highlights a critical approach to wild problems: privileging principles over calculated trade-offs. When Teodora, a housekeeper at a lodge in the Grand Tetons, found a diamond earring while cleaning a room, she could have kept it with little risk of discovery. Instead, she left a note for the previous guests. Her decision wasn't about weighing potential reward against the minimal risk of being caught. Rather, she saw herself as an honest person and acted accordingly. For Teodora, there was no trade-off to consider - her sense of self came first. The standard economic view would suggest that everyone has their price - an amount of money or other benefit they would accept to violate their principles. While incentives certainly influence behavior, this framing misses something profound about human character. When our core values are at stake, we resist making trade-offs. We don't want our virtue to have a price, even if sometimes it does. Our anger at the suggestion that we can be "bought" reveals our aspiration toward integrity. This leads to a powerful decision framework: for choices that implicate your core identity, don't consider the cost. Save your sense of self. Return the diamond, no matter how large. Nothing cancels out betraying who you are or who you aspire to be. The first virtue of this approach is simplicity - having a rule means spending less time deliberating and suffering. You have a default that guides your actions: "I am the kind of person who always returns lost objects" or "I am the kind of person who visits friends in the hospital." The second virtue is more profound: rules prevent us from fooling ourselves. Without clear principles, we effortlessly rationalize decisions that betray our better selves. As Benjamin Franklin observed, "So convenient a thing it is to be a reasonable Creature, since it enables one to find or make a Reason for every thing one has a mind to do." Rules help us maintain who we are and who we want to become. Even more importantly, principles can guide aspiration. Philosopher Harry Frankfurt notes that humans uniquely have desires about our desires - we might want to have a conscience even if we currently lack one. Through practice and habit, we can develop the virtues we aspire to embody. In Max Beerbohm's story "The Happy Hypocrite," a wicked man wears a mask of saintliness to win a virtuous woman's heart, only to discover that his face has transformed to match the mask. Through changed behavior, he changed his character.

Chapter 5: Living Like an Artist: Embracing Uncertainty and Creating Yourself

William Faulkner once described writing a book as getting "the character in your mind. Once he is in your mind, and he is right, and he's true, then he does the work himself. All you need to do then is to trot along behind him and put down what he does and what he says." This organic, emergent approach to creation offers a powerful model for how we might approach wild problems in life. Instead of executing a predetermined plan, we can allow our path to unfold through the process of living it. Some fortunate individuals have what might be called a "prefab" life - they know early on they want to be doctors or engineers, they follow the prescribed path, and they succeed. But most of us don't have such clarity. We find ourselves in unfamiliar territory with little guidance about what might bring us fulfillment. What we want, what we enjoy, and what gives our lives meaning emerges from the choices we make and what we learn from living with those consequences. Elizabeth Bishop's poem "One Art," widely considered one of the finest villanelles ever written, took seventeen drafts to reach its perfection. The poem wasn't fully planned in advance - it emerged through the process of creation, with the form itself seeming to make demands on the poet. Similarly, our lives aren't fully planned or controlled. They emerge through our interaction with circumstances, opportunities, and challenges. Living like an artist means being open to discovery about the world and yourself. It requires a willingness to engage with uncertainty rather than merely trying to eliminate it. Artists often have no idea what they're going to create when they begin - they make art in order to know what they are planning. Picasso observed, "To know what you're going to draw, you have to begin drawing." So it is with life. This perspective has practical implications. On one hand, it suggests the importance of saying yes to experiences that might expand your horizons, even when their value isn't immediately obvious. Serendipity plays a crucial role in discovering what you enjoy and what brings meaning to your life. On the other hand, it means recognizing when to abandon plans that aren't working, when dreams become nightmares you should walk away from. Living like an artist also means seeing yourself as the work of art - as clay to be molded or marble to be sculpted. You become an "artifactual man," as economist James Buchanan put it, crafting yourself through your choices. This requires self-awareness and aspiration - thinking about what you want to become, even if you don't know the precise shape of what you're striving toward. The movie Babette's Feast captures this spirit when a character remarks: "Through all the world there goes one long cry from the heart of the artist - give me leave to do my utmost." Doing your utmost doesn't always mean racing at full speed. Sometimes it means slowing down, paying attention, and being ready for what comes next.

Chapter 6: Optionality and Adaptability: The Belichick Strategy for Life

Bill Belichick, the extraordinarily successful head coach of the New England Patriots, offers surprising wisdom for approaching wild problems. While NFL teams invest enormous resources analyzing college players before the draft, Belichick takes a different approach. Rather than believing his team can perfectly predict which players will succeed, he embraces his ignorance about the future and develops strategies that account for this uncertainty. Belichick frequently trades higher draft picks for multiple lower picks, valuing quantity over supposed quality. He understands that despite extensive data and analysis, it remains extremely difficult to predict which college players will thrive in the NFL. Instead of focusing all his energy on making the perfect draft decision, he increases his options by selecting more players and then evaluating them firsthand during training camp. This approach acknowledges that some aspects of performance can only be assessed through direct experience. This strategy embodies the principle of optionality - having the freedom to do something without the obligation. Like Zappos offering free returns on shoes, optionality allows you to try something while maintaining the ability to change course if it doesn't work out. When facing wild problems, optionality means trying more experiences rather than agonizing over which single path might be best. Instead of spending excessive time researching which choice might be perfect, you can sample different options and discover what resonates through direct experience. Belichick also demonstrates the importance of being willing to abandon sunk costs. He doesn't feel compelled to keep high draft picks who underperform simply because of their status. He recognizes that some decisions inevitably turn out differently than expected, not because of poor judgment but because prediction is inherently limited. Life choices that disappoint aren't "mistakes" in the traditional sense - they're ventures that revealed information you couldn't have known in advance. This perspective challenges conventional wisdom about grit and persistence. While giving up immediately at the first sign of difficulty is rarely wise, mindlessly persisting with choices that clearly aren't working wastes precious time. If you hate law school and hate being a lawyer, try a different type of law. If that doesn't help, changing careers isn't failure - it's adaptation based on new information about yourself and your circumstances. Wild problems are painful partly because of the specter of regret. But the Belichick strategy suggests spending less time trying to make the "perfect" decision and more time developing approaches that allow for adaptation when things don't go as planned. Rabbi Jonathan Sacks observed, "The only way to understand marriage is to get married... Those who hover on the edge of a commitment, reluctant to make a decision until all the facts are in, will eventually find that life has passed them by." All the facts are never in.

Chapter 7: Ensemble Thinking: Getting Over Yourself and Building Connections

Human beings are hardwired to see themselves as the main characters of their own reality shows. We experience life as a narrative in which we face big decisions, overcome obstacles, and pursue goals, with everyone else relegated to supporting roles. This self-centered perspective is natural but limiting. It shapes how we interact with others and ultimately restricts our capacity for connection and meaning. An alternative approach is to view life through the lens of an ensemble cast. In shows like Friends or movies like Love Actually, no single character dominates the narrative. The story emerges from their relationships and interactions. Similarly, we can choose to see ourselves not as lone protagonists but as part of something larger, weaving in and around others in unexpected and meaningful ways. This shift in perspective transforms how we experience daily interactions. Consider a conversation with a friend. With a self-centered approach, you might prepare anecdotes in advance, focus on making your points, and afterward congratulate yourself on your eloquence. But from an ensemble perspective, the conversation becomes an emergent experience without a predetermined script. You give your full attention without planning your next remark, allowing something organic and unpredictable to unfold. Psychiatrist Iain McGilchrist notes that the right hemisphere of the brain processes experience differently than the left, focusing on connection and "betweenness" rather than isolated parts. It sustains a sense of continuous being in the world rather than breaking experience into discrete elements. Strengthening this capacity for connection helps us escape the gravitational pull of self-absorption. Rabbi Jonathan Sacks distinguished between contracts and covenants. In contractual relationships, you keep score and worry about being exploited. But covenants are promises based on commitment rather than calculation. They allow interactions to be free from constant cost-benefit analysis. Marriage, Sacks said, turns love into loyalty, taking both parties beyond "what's in it for me." Getting over yourself doesn't mean abandoning self-care or ignoring your needs. Rather, it means recognizing that your deepest fulfillment often comes through connection rather than achievement or consumption. By seeing yourself as part of an ensemble rather than the star of the show, you experience life's texture differently - richer and more satisfying. In practice, this means being fully present with others rather than mentally rehearsing your next remark. It means privileging relationships over efficiency in many contexts. It means understanding that friendship and family aren't just resources for your benefit but opportunities to contribute to something larger than yourself. On the dance floor of life, make room for other dancers and let your partner shine. In the choir of life, lower your voice and revel in the harmony.

Summary

Wild problems demand a fundamentally different approach than the decision frameworks we apply to more straightforward challenges. Unlike tame problems where data, algorithms, and rational analysis lead to steady progress, life's biggest decisions involve uncertainty that cannot be eliminated, identity transformations that cannot be fully anticipated, and questions of meaning that resist quantification. The conventional view of rationality - weighing costs and benefits to maximize personal utility - proves inadequate when confronting choices that define who we are. Instead of seeking certainty or striving to identify the "best" option, we might embrace uncertainty and recognize it as inherent to the human condition. This means privileging principles over narrow self-interest, developing optionality rather than committing prematurely, seeing ourselves as works in progress rather than finished products, and embracing an ensemble mentality that values connection over self-maximization. The path to flourishing isn't found through ever more precise calculations but through integrity, meaning, and purpose - elements that transcend momentary pleasures and pains. By approaching life's wild problems with humility about what we can know and clarity about what truly matters, we discover that uncertainty isn't merely something to tolerate but potentially the very soil in which a meaningful life takes root.

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Russell "Russ" Roberts

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