How to Decide

Picture this: you're standing at a crossroads in your career, holding two equally attractive job offers. Your heart races as you weigh the options, knowing that this choice could shape the next chapter of your life. Yet despite the importance of the decision, you find yourself paralyzed, unsure of how to proceed. If this scenario feels familiar, you're not alone. Research shows that the average person spends over 250 hours per year just deciding what to eat, watch, and wear—time that could be better invested in making truly meaningful choices.

The quality of our decisions determines the trajectory of our lives more than any other factor within our control. While we cannot control luck or external circumstances, we can master the art of decision-making itself. Every day presents us with countless opportunities to move closer to or further from our goals, and the cumulative effect of these choices compounds over time like interest in a savings account. The challenge isn't that we lack intelligence or good intentions—it's that most of us have never been taught a systematic approach to making better decisions.

At the heart of poor decision-making lies a dangerous trap called "resulting"—the tendency to judge the quality of a decision based solely on its outcome. This mental shortcut seems logical at first glance: if something worked out well, it must have been a good decision, right? Unfortunately, this backwards reasoning leads us astray more often than we realize.

Consider the story of United Artists, the film studio that passed on a scrappy science fiction project in the early 1970s. The movie they rejected? Star Wars. Today, it's easy to label this as one of the worst business decisions in entertainment history. After all, the Star Wars franchise has generated over ten billion dollars in box office revenue alone. However, this conclusion overlooks a crucial reality: at the time of the decision, United Artists executives were working with incomplete information about an unproven concept from a young filmmaker.

The truth is that even the best decisions sometimes lead to poor outcomes, and even terrible decisions occasionally result in spectacular success. Luck intervenes between our choices and their results, creating a gap that resulting fails to acknowledge. When we evaluate past decisions based purely on how they turned out, we miss valuable lessons about what actually constitutes good decision-making.

To break free from resulting, we must learn to separate decision quality from outcome quality. This means asking different questions: What information was available at the time? What process was used to reach the conclusion? Were the reasoning and analysis sound given what could reasonably be known? By focusing on these elements rather than just the end result, we can extract genuine wisdom from our experiences.

The goal isn't to ignore outcomes entirely—they contain important feedback about our predictions and assumptions. Instead, we must view them in proper context, recognizing that a single result tells us little about decision quality. Only by examining patterns across multiple decisions can we begin to distinguish skill from luck and truly improve our judgment over time.

Great decisions emerge from a clear-eyed view of the future, built on three fundamental pillars: understanding what could happen, knowing what we value, and estimating the likelihood of various outcomes. These three P's—possibilities, preferences, and probabilities—form the foundation of any sound decision-making framework.

The power of this approach becomes clear in the story of Dr. Ignaz Semmelweis, a young physician working in Vienna General Hospital's obstetrics ward in 1847. Faced with a devastating mortality rate from childbed fever, Semmelweis mapped out the possible causes, considered what outcomes he most wanted to avoid, and estimated the probability that contamination from cadavers was killing new mothers. When he instituted mandatory handwashing, mortality rates plummeted from 16% to 2%—a dramatic validation of his systematic approach to an uncertain situation.

The first step involves expanding your view of what's possible. Too often, we make decisions while seeing only a narrow slice of potential futures. Like standing at the base of a mountain, our current vantage point limits our perspective. By deliberately considering a wider range of outcomes—both positive and negative—we develop a more complete picture of what we're choosing between.

Next comes clarifying your preferences and understanding the payoffs associated with each possibility. What do you value most? What risks are you willing to accept? What would constitute success or failure? These aren't abstract philosophical questions—they're practical considerations that should directly influence your choice. Take time to order potential outcomes from most to least desirable, considering both the magnitude and nature of what you might gain or lose.

Finally, we must wrestle with probabilities, even when we lack perfect information. The goal isn't mathematical precision but rather developing educated estimates about likelihood. Start with everyday language—words like "likely," "possible," or "unlikely"—then gradually work toward more specific assessments. Remember, all estimates are educated guesses, and an imperfect forecast is infinitely more valuable than no forecast at all.

One of the most paralyzing aspects of decision-making is the fear that we're not investing enough time and energy in reaching the perfect choice. This perfectionist impulse, while well-intentioned, often traps us in analysis paralysis and prevents us from making any progress at all. The key to breaking free lies in understanding the fundamental trade-off between speed and accuracy, then calibrating our approach to match the situation at hand.

The solution begins with what's called the "Happiness Test"—a simple but powerful way to gauge whether a decision deserves extensive deliberation. Ask yourself: if this choice doesn't work out as planned, how much will it affect my happiness in a week, a month, or a year? If the honest answer is "not much," you've identified a low-impact decision that deserves a correspondingly low investment of time and mental energy.

Consider the phenomenon of "freerolling"—situations where the potential upside significantly outweighs the downside risk. Imagine you're considering applying to a dream college that seems like a long shot, or making an offer on a house that's slightly above your target price. In these scenarios, the worst-case outcome leaves you no worse off than you were before, while the best case could be transformational. When you recognize a freeroll, the decision becomes simple: act quickly to seize the opportunity, then invest your saved time in more complex choices.

Perhaps counterintuitively, some of our most agonizing decisions are actually the easiest ones in disguise. When you're torn between two genuinely excellent options—say, choosing between Paris and Rome for a dream vacation—the very difficulty of the choice reveals its simplicity. If both options would make you happy, then whichever one you pick, you can't be that wrong. Apply the "Only-Option Test": if this were your only choice, would you be satisfied? If you answer yes to multiple options, flip a coin and move on.

The goal isn't to rush every decision or eliminate careful thought from your process. Instead, it's about developing the wisdom to distinguish between choices that merit deep analysis and those that call for swift action. By matching your decision-making intensity to the stakes involved, you'll find yourself making better choices while reclaiming precious time for what matters most.

While positive thinking has dominated self-help culture for decades, there's profound wisdom in deliberately imagining how things might go wrong. This approach, known as mental contrasting, doesn't stem from pessimism or fear—it emerges from a practical recognition that obstacles are inevitable, and our best defense is thoughtful preparation.

The technique of conducting a "premortem" illustrates this principle beautifully. Imagine you've committed to a challenging goal—perhaps starting a business, completing a difficult project, or maintaining a new healthy habit. Rather than simply visualizing success, transport yourself to a future point where you've failed to achieve your objective. From that imagined vantage point, work backwards to identify the most likely reasons for failure. What internal factors might derail you? What external circumstances could intervene? What would you wish you had done differently?

This process of prospective hindsight serves multiple purposes. First, it helps you spot potential problems while you still have time to address them. Second, it reduces the emotional impact of setbacks by mentally rehearsing them in advance. When challenges do arise—as they inevitably will—you'll recognize them as anticipated difficulties rather than devastating surprises. Finally, it enables you to create "precommitment contracts" with yourself, establishing barriers that make it harder to abandon your goals when motivation wanes.

Consider complementing your premortem with its positive counterpart: a "backcast" that envisions success and traces the path that led there. What decisions proved crucial? What support systems made the difference? What skills or resources were most valuable? This dual approach—combining realistic preparation for failure with clear vision of success—provides a more complete map for navigating toward your goals.

The power of negative thinking extends beyond individual planning to encompass what might be called the "Dr. Evil" game. Imagine that an evil genius has taken control of your brain, intent on making you fail while avoiding detection. This villain wouldn't force you to make obviously terrible decisions—those would be too easily spotted and corrected. Instead, they would nudge you toward choices that seem reasonable in isolation but guarantee failure when repeated over time. Perhaps an extra donut "just this once," or hitting the snooze button because you had "a really hard day." By identifying these seemingly innocent but cumulatively destructive patterns, you can make category decisions that remove temptation from future moments of weakness.

Just as medical professionals wash their hands to prevent the spread of infection, decision-makers must practice intellectual hygiene to avoid contaminating the feedback they receive. The human tendency to seek confirmation rather than correction means that well-intentioned advice often reinforces our existing beliefs rather than challenging them with fresh perspectives.

The problem begins with how we frame our requests for input. When you share your opinion before asking for someone else's perspective, you've already infected them with your viewpoint. Like the famous psychology experiment where people agreed that obviously different-length lines were the same after hearing others make that claim, our beliefs are powerfully contagious. The solution requires discipline: quarantine your own opinions when seeking feedback from others.

This principle becomes even more critical in group settings, where the first person to speak often sets the tone for everyone who follows. Research demonstrates that teams frequently fail to share crucial information that contradicts emerging consensus, even when individual members possess knowledge that could improve the final decision. Combat this tendency by soliciting initial opinions independently—through email or written responses—before bringing the group together for discussion.

The legendary poker player's approach to getting feedback on difficult hands illustrates proper decision hygiene in action. Rather than saying, "I folded my cards and lost the pot—what do you think?" they would describe the situation neutrally: "The player before me raised, I had ace-queen—what would you do?" By withholding both their actual choice and its outcome, they created space for genuine, uncontaminated advice.

Consider anonymizing initial feedback when status differences might influence responses. Junior team members often hesitate to contradict senior colleagues, even when they possess valuable insights. Similarly, create checklists of relevant information that must be provided before feedback can be given. Just as you wouldn't ask a doctor for medical advice while withholding crucial symptoms, don't seek decision guidance while omitting key facts about your situation.

Remember that discovering disagreement is a gift, not a threat. When someone's perspective diverges from yours, one of three valuable things is happening: the truth lies somewhere between your positions, you're wrong and can correct your thinking, or you're right but will deepen your understanding by explaining your reasoning. All three outcomes improve your decision-making capacity.

The journey toward better decision-making isn't about achieving perfection or eliminating uncertainty from our choices. Instead, it's about developing reliable processes that help us navigate an inherently unpredictable world with greater wisdom and skill. As this exploration has revealed, the quality of our decisions depends far more on our approach than on our ability to predict the future with perfect accuracy.

The tools and frameworks we've examined work together to create a comprehensive system for improvement: learning to separate decision quality from outcome quality, systematically considering possibilities and probabilities, matching our analytical intensity to the stakes involved, preparing for obstacles through negative thinking, and maintaining intellectual hygiene when seeking feedback. Each element strengthens the others, creating a foundation for choices that align with our values and move us closer to our goals. The path forward is clear and immediately actionable: start by applying the Happiness Test to one decision you're currently facing, and experience firsthand how proper categorization can free up mental energy for choices that truly matter.