How to Decide

How to Decide Plot Summary

Introduction

Every day, you make thousands of decisions that shape your life's path. Some are trivial—what to eat for breakfast or which movie to watch. Others carry profound consequences—changing careers, investing savings, or choosing a life partner. What if you could peer into a crystal ball that revealed which decisions would lead to success and which to regret? While perfect foresight remains elusive, this book offers something perhaps more valuable: a framework for making decisions that increases your chances of positive outcomes regardless of what unpredictable factors lie ahead. By understanding how to evaluate possibilities, recognize your biases, and implement practical decision-making tools, you'll develop your own version of that mythical crystal ball—not one that guarantees perfect outcomes, but one that substantially improves your decision quality when it matters most.

Chapter 1: Recognize When Outcomes Cloud Judgment

At the heart of poor decision-making lies a simple but powerful trap: we judge our decisions by their outcomes rather than by the quality of the thinking that went into them. This phenomenon, called "resulting," creates a misleading connection between decision quality and outcome quality. Consider this scenario: You quit your job to take a position at a new company. If a year later you've received a promotion and love your colleagues, you'll likely view your decision as brilliant. If instead you've been laid off and were miserable, you'll probably consider it a terrible decision. Yet in both cases, the information you had when making the choice was identical—only the outcome differed. This distortion isn't limited to career choices. Investors who purchase a stock that quadruples in price pat themselves on the back for their wisdom, while those whose investments collapse blame their judgment. The truth is that any decision creates a range of possible outcomes, some influenced by skill and others by luck. Just as you can run a red light without consequence or proceed through a green light and get hit by a distracted driver, outcomes don't perfectly reflect decision quality. To combat resulting, we must separate the quality of the decision from the quality of the outcome. This means recognizing four possible combinations: good decisions with good outcomes (Earned Rewards), good decisions with bad outcomes (Bad Luck), bad decisions with good outcomes (Dumb Luck), and bad decisions with bad outcomes (Just Deserts). By acknowledging all four possibilities, we create a more accurate framework for evaluating our choices. When evaluating past decisions, try reconstructing what you knew at the time, not what you know now. Ask yourself: "What information did I have available?" and "What were the reasonable possibilities I could foresee?" This perspective helps you learn the right lessons from experience and improves future decision-making by focusing on process rather than results. Remember, the goal isn't to guarantee perfect outcomes—that's impossible in an uncertain world. The goal is to make decisions that, over time, tilt the odds in your favor through thoughtful consideration of possibilities, preferences, and probabilities.

Chapter 2: Embrace Both Inside and Outside Views

When making decisions, we naturally default to what psychologists call the "inside view"—our personal perspective based on our specific circumstances, beliefs, and experiences. While this viewpoint feels intuitive, it often blinds us to objective reality and limits our decision quality. Consider the story of someone whose friend constantly complains about dating "jerks." From the outside, it's obvious that the friend's own dating patterns contribute to this recurring problem. Yet the friend, trapped in the inside view, sees only bad luck or a "curse." Similarly, studies show that over 90% of professors rate themselves as better-than-average teachers, and 90% of Americans believe they're better-than-average drivers—statistically impossible claims that reveal our tendency toward self-flattering distortions. These blind spots aren't corrected by intelligence; in fact, being smart can make things worse. Research shows that intelligent people are better at motivated reasoning—finding convincing justifications for what they already believe. They construct persuasive narratives that convince both themselves and others, making it harder to recognize when they're wrong. The antidote is deliberately seeking the "outside view"—what's generally true regardless of your particular situation. For example, if you're considering starting a restaurant and estimate a 90% chance of success, learning that 60% of new restaurants fail in their first year provides a crucial reality check. Base rates like these serve as gravitational centers that should influence your forecasts. To implement this approach, try a technique called Perspective Tracking. First, describe your situation entirely from the outside view, incorporating relevant statistics and others' perspectives. Then separately describe it from your inside view. Finally, marry these viewpoints to reach a more accurate understanding. This marriage between perspectives doesn't mean ignoring your unique insights. Rather, it acknowledges that accuracy lives at the intersection of general truths and specific circumstances. By anchoring first to the outside view and then adjusting based on particular factors, you create a decision framework less susceptible to self-deception. This approach requires humility—admitting that our personal perspective might be flawed. But that temporary discomfort leads to substantially better decisions, as demonstrated by professional investors who establish boundaries around their "circle of competence" to avoid fooling themselves about opportunities outside their expertise.

Chapter 3: Weigh Possibilities with Clarity

Making good decisions requires envisioning how the future might unfold. Yet most of us struggle with accurately forecasting probabilities, often using vague terms like "likely," "possibly," or "rarely" instead of precise estimates. Dr. Annie Duke recounts an experiment where she asked participants to estimate the weight of a bison at Yellowstone National Park. While most people couldn't pinpoint the exact weight, almost everyone provided reasonable estimates within a certain range—no one guessed 10 pounds or 50,000 pounds. This demonstrates that even with imperfect information, we know more than we think we do. The problem isn't lack of knowledge but reluctance to make educated guesses. When Michael and Andrew Mauboussin surveyed people about probability terms, they discovered enormous variation in interpretation. When someone says an outcome has a "real possibility," different listeners might understand this as meaning anywhere from a 20% to 80% chance. This ambiguity creates miscommunication that undermines decision quality. To improve decision-making, we need to adopt what Duke calls "the Archer's Mindset." An archer aims at a target's bull's-eye, knowing they may not hit it perfectly but will score points by landing somewhere on the target. Similarly, we should make our best estimates even knowing they won't be perfectly accurate. Consider how this applies to practical decisions. If you're choosing between two job candidates, don't just list pros and cons. Instead, estimate specific probabilities: What's the likelihood each candidate will still be with your company in six months? In two years? Making these explicit predictions forces you to examine your reasoning and creates accountability for your decision process. When making estimates, include both a specific number (your "bull's-eye") and a range that reflects your uncertainty. The width of this range signals how confident you are. For instance, if estimating a bison's weight, your bull's-eye might be 1,800 pounds with a range of 1,100 to 3,500 pounds. This approach acknowledges uncertainty while still providing useful information. To test whether your ranges are reasonable, use the "shock test": Would you be genuinely surprised if the true answer fell outside your range? If not, your range is too narrow. Most people are overconfident in their estimates, with studies showing that when people aim for 90% confidence intervals, they typically capture the correct answer only about 50% of the time. By expressing probabilities precisely and acknowledging uncertainty appropriately, you create more opportunities to learn from disagreement. When someone estimates a different probability than you do, that difference becomes immediately apparent, creating valuable opportunities to update your thinking.

Chapter 4: Escape Analysis Paralysis

How much time do you spend deciding what to eat, what to watch on streaming services, or what to wear? Research shows the average person spends over 250 hours per year—equivalent to seven workweeks—on these routine choices alone. This "analysis paralysis" consumes valuable time that could be better spent elsewhere. Decision-making always involves a trade-off between time and accuracy. The more time you invest, the more accurate your decision might be. The challenge is finding the right balance for each situation. Not every decision deserves hours of deliberation, yet most of us struggle to identify when we can decide faster. The Happiness Test offers a simple solution: ask yourself, "Will this decision significantly affect my happiness in a year? A month? A week?" If the answer is no, you can decide quickly. What you eat for dinner tonight will rarely impact your happiness next week, let alone next year. For low-impact decisions that repeat frequently, you can move even faster. Since you'll get another chance at the same choice soon (like what to eat tomorrow), the cost of a suboptimal decision is minimal. The potential regret from ordering the wrong entrée diminishes when you know you'll get another opportunity shortly. Another mental model that can speed decision-making is recognizing "freerolls"—situations with limited downside but substantial upside potential. Imagine someone offers you $10 if you correctly answer a trivia question, with no penalty for wrong answers. That's a freeroll. Similarly, applying to a dream college that seems like a reach, or making a reasonable offer on your dream house below asking price, presents minimal downside with potentially life-changing upside. Counterintuitively, difficult decisions between seemingly equal options should also be made quickly. When choosing between vacationing in Paris or Rome—both amazing destinations—the very difficulty signals that either choice would be satisfactory. Use the "Only-Option Test": ask yourself, "If this were my only choice, would I be happy with it?" If both options pass this test, you can't be significantly wrong either way, so decide quickly, even by flipping a coin. For decisions with easily reversible outcomes, embrace "quit-to-itiveness" rather than "stick-to-itiveness." Recognize that many decisions aren't permanent. Jeff Bezos calls these "two-way-door decisions"—choices you can back out of if they don't work out. When the cost of changing course is low, you can decide faster and learn through experimentation. The key insight is to allocate your decision-making time wisely. Spend time sorting options into "acceptable" and "unacceptable" categories, but once you've identified multiple acceptable options, save time by picking among them quickly. This "Menu Strategy" ensures you invest your mental energy where it matters most.

Chapter 5: Practice Productive Negative Thinking

Much of the self-help industry preaches the power of positive thinking—visualizing success will supposedly manifest desired outcomes. Books like "The Secret" even claim that positive thoughts magnetically attract positive results. Yet research suggests negative thinking, properly applied, can be far more effective for achieving goals. Consider New Year's resolutions. Within a week, 23% are abandoned, and ultimately 92% of people never achieve their resolution goals. Why? Because simply visualizing success doesn't prepare us for obstacles. Mental contrasting—imagining potential barriers to our goals—provides a more reliable path to achievement. Gabriele Oettingen, a psychology professor at NYU, conducted over two decades of research on this approach. In one study, participants in a weight-loss program who practiced mental contrasting lost 26 more pounds on average than those who relied solely on positive visualization. Similar results appeared across domains from academic achievement to career advancement. To harness negative thinking productively, use a technique called a "premortem." Developed by psychologist Gary Klein, a premortem asks you to imagine yourself in the future having failed to achieve your goal, then work backward to identify what went wrong. Unlike a postmortem, which examines failure after it occurs, a premortem helps you anticipate and address problems before they happen. For example, if you're planning to exercise more regularly, imagine it's six months from now and you've gone to the gym only three times. Why did that happen? You might identify reasons within your control (hitting snooze too often, not scheduling workouts) and factors outside your control (unexpected work demands, injury). This exercise typically reveals 30% more potential obstacles than standard planning. A complementary technique is the "Dr. Evil game." Imagine an evil genius has taken control of your brain and wants to make you fail in a way that's hard to detect. Dr. Evil won't make you do obviously terrible things—that would reveal his presence. Instead, he'll cause you to make small, justifiable decisions that collectively guarantee failure. For a nutrition goal, Dr. Evil might prompt you to make exceptions for special occasions, work situations, or social events that, taken together, completely undermine your plan. Once you've identified potential obstacles, create precommitment contracts to raise barriers against poor decisions. Just as Ulysses had himself tied to the mast to resist the Sirens' song, you can establish mechanisms that prevent self-sabotage. This might mean setting up automatic transfers to retirement accounts, keeping unhealthy foods out of your home, or declaring your intentions to friends who will hold you accountable. These techniques don't just prevent failure—they increase the likelihood of success by helping you prepare for setbacks that might otherwise derail your progress. While positive thinking helps establish worthwhile goals, negative thinking provides the practical pathway to achieving them.

Chapter 6: Maintain Decision Hygiene

Have you ever noticed how people tend to agree with your opinions when you share them first? This isn't coincidence—it's evidence of a phenomenon called "belief contagion" that undermines effective decision-making. In a classic experiment, psychologist Solomon Asch demonstrated how social pressure influences perceptions. Participants were asked to identify which of three lines matched a reference line—an objectively clear task. When planted confederates deliberately gave incorrect answers before real participants responded, 36.8% of subjects conformed to the wrong answer rather than trusting their own eyes. This tendency to conform creates a serious problem for decision-makers seeking honest feedback. When you share your opinion before asking for someone else's view, you "infect" their response. They may unconsciously shift their thinking to align with yours or consciously adjust their answer to avoid disagreement. To combat this contamination, practice what Duke calls "decision hygiene"—quarantining your opinions when seeking feedback. Just as Dr. Ignaz Semmelweis discovered in 1847 that doctors needed to wash their hands between patients to prevent infection, decision-makers need to prevent their beliefs from spreading to others when genuine perspectives are needed. In practice, this means asking neutral questions without revealing your stance. Instead of saying, "I think Candidate A is the best fit for this position. What do you think?", simply ask, "Which candidate do you think is the best fit?" This subtle difference yields dramatically more honest responses. For group decisions, the problem compounds. Once the first person shares an opinion, it influences everyone else. Research by Garold Stasser and William Titus showed that even when group members collectively possess all information needed to make an optimal choice, they often fail to share critical details that contradict emerging consensus. To preserve independent thinking in groups, solicit initial opinions and rationales from each member independently before any discussion occurs. This can be done via email or written responses. For lower-stakes decisions, have group members write down their views before sharing, starting with the most junior person to minimize status effects. Another crucial aspect of decision hygiene involves providing complete information. When seeking feedback, we naturally spin narratives to highlight details supporting our preferred conclusion while downplaying contradictory evidence. Combat this by creating a checklist of relevant information that must be shared when seeking advice on recurring decisions. The goal isn't to eliminate disagreement but to reveal genuine differences in perspective. These differences expose blind spots in our thinking and offer valuable corrective information. Maintaining decision hygiene ensures that when you ask for input, you get what you actually need—honest feedback—rather than what feels comfortable: confirmation of what you already believe.

Chapter 7: Build Your Decision Toolkit

Decision-making doesn't require supernatural abilities, but it does demand a reliable set of mental tools that help you navigate uncertainty. Throughout this book, we've explored techniques that collectively form a comprehensive decision toolkit for confronting life's choices, large and small. For evaluating past decisions, tools like Knowledge Tracking help separate what you knew at the time from what became apparent only later, preventing hindsight bias. Decision trees with counterfactuals remind you of all possible outcomes that could have occurred, not just the one that did. Perspective Tracking ensures you view situations both from your personal standpoint and through objective, outside lenses. For new decisions, the Six-Step Decision Process provides a systematic approach: identify possible outcomes, clarify your preferences, estimate probabilities, assess options, compare alternatives, and decide. This structure transforms vague intuitions into explicit reasoning that can be examined and improved. Time-saving frameworks like the Happiness Test, the Only-Option Test, and recognizing freerolls help you allocate your limited decision-making resources efficiently. Preparation tools like premortems and backcasting enable you to anticipate obstacles and plan responses before they arise. Remember that perfect decisions are impossible in an uncertain world. As Duke writes, "Your decisions are like a portfolio of investments. Your goal is to make sure that the portfolio as a whole advances you toward your goals, even though any individual decision in that portfolio might win or lose." This investment mindset frees you from the paralysis of perfectionism while maintaining focus on long-term improvement. The most valuable insight may be recognizing that genuine feedback—particularly when it contradicts your initial thinking—is a gift, not a threat. By practicing decision hygiene and actively seeking diverse perspectives, you create opportunities to refine your understanding and strengthen your choices.

Summary

Life offers no crystal balls to reveal our future, but it does provide something more valuable: the ability to improve our decision-making process. By understanding how biases like resulting and hindsight distort our judgment, and by implementing practical tools like premortems, decision trees, and outside-view thinking, we can significantly enhance our ability to navigate uncertainty. As Duke reminds us, "The only thing you have control over that can influence the way your life turns out is the quality of your decisions." We cannot control luck—the unpredictable factors that intervene between our choices and their outcomes—but we can control how we approach decisions themselves. By embracing this philosophy, we stop chasing the illusion of perfect certainty and instead focus on building robust decision processes that improve our odds over time. Begin today by applying just one technique from this toolkit to your next important decision. Perhaps conduct a premortem to anticipate obstacles, seek feedback without revealing your opinion first, or explicitly estimate probabilities instead of using vague terms. Through consistent practice and thoughtful refinement, you'll develop your own version of that mythical crystal ball—not one that guarantees perfect outcomes, but one that provides clearer vision when it matters most.

About Author

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Annie Duke

Annie is the co-founder of The Alliance for Decision Education, a non-profit whose mission is to improve lives by empowering students through decision skills education. She is also a member of the National Board of After-School All-Stars and the Board of Directors of the Franklin Institute. In 2020, she joined the board of the Renew Democracy Initiative.

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