Perfectly Confident

Can you ever be too confident? Don A. Moore argues that you absolutely can—and that both extremes of confidence, too high or too low, can sabotage your decisions, relationships, and success. In Perfectly Confident, Moore challenges the popular self-help mantra that more confidence is always better. He contends that confidence should be neither a swagger nor self-doubt but a careful calibration of what you believe against what is true. The goal is not blind optimism; it’s an honest belief aligned with evidence.

Moore draws from decades of psychological and behavioral economics research, as well as his own life, to show how overconfidence and underconfidence each lead to their own kinds of error. Overconfidence produces “errors of action”—risky leaps you later regret—while underconfidence breeds “errors of inaction,” missed opportunities you’ll never get back. His central mission is teaching you to find the middle way: the narrow, evidence-based path between arrogance and timidity.

Why Confidence Is Misunderstood

Moore begins by admitting his own history as a believer in the “power of positive thinking.” As a teenager, he tried subliminal tapes claiming to make him more popular; as an adult, he attended Tony Robbins’s fire walk event, where his overconfidence literally burned his feet. These stories set the tone for the book’s exploration of why society idolizes confidence as a cure-all. Self-help literature, from Dale Carnegie’s successors to modern motivational gurus, often preaches that your goal should be to maximize confidence, as though courage alone guarantees success. Moore sharply disagrees. If there are confidence disorders—like believing you can drive blindfolded—then you can definitely have too much of it.

To combat this myth, he redefines confidence as a belief about a future outcome or performance that must be tested against actual results. Confidence is not personality or self-worth; it’s an assessment of reality. Shaquille O’Neal dunking a basketball is confident; Moore’s child thinking he could dunk if he tried hard enough is overconfident. Confidence becomes “perfect” when it reflects what evidence warrants.

The Three Faces of Confidence

Throughout the book, Moore distinguishes between three dimensions that keep confidence honest: Estimation (how good you think you are), Placement (how you rank compared to others), and Precision (how sure you are that you’re right). Overconfidence appears in each: overestimating your abilities or chances, overplacing yourself above others, and overprecision—being too sure about uncertain facts. If you think you’ll finish a project in two days when it takes ten, that’s overestimation. Believing you’re a safer driver than the rest of your city exemplifies overplacement. And assuming your stock-market prediction is guaranteed shows overprecision.

Interestingly, underconfidence has its own perils. When people feel less capable at rare or difficult tasks, they experience impostor syndrome. Moore cites Maya Angelou, John Steinbeck, and Jodie Foster—all extraordinary achievers—who confessed fears that their success was luck. Their doubts mirror what many competent people secretly feel: since they know their own struggles intimately but not others’, they assume everyone else is better.

The Middle Way

Moore proposes the Aristotelian “middle way,” drawing from Aristotle’s and Theodore Roosevelt’s advice to avoid both rashness and timidity. Perfect confidence is not arrogance or self-sabotage—it’s the truth about your abilities and your odds. That means calibrating beliefs using facts, feedback, and probabilities, not wishful thinking. It’s about seeing clearly what is possible, what isn’t, and where the data actually lie.

“Confidence isn’t about fooling yourself into believing you can walk through fire—because you’ll get burned if you try.”

Moore teaches that confidence doesn’t grow from affirmations or posture; it grows from calibration. Those who master it make better bets—in careers, investments, relationships, and even self-belief. The book’s eight chapters act as a toolkit: they show how confidence leads us astray (Part I: Over and Under) and how to recalibrate it back to truth (Part II: Just Right). Using psychology, philosophy, and real-world disasters—from Boeing’s flawed plane software to the 2008 crisis—Moore demonstrates that arrogance and fear are twin mirrors of misunderstanding reality. By learning to trust your reason, scrutinize your beliefs, and see both risk and potential with sober eyes, you can develop what he calls perfect confidence: a state of mind where optimism meets evidence and self-belief meets truth.

Moore calls overconfidence “the mother of all biases,” and for good reason: it’s the silent engine behind some of history’s worst disasters and countless everyday mistakes. From the sinking of the Titanic to the 2008 financial crisis, overconfidence lures even smart people into believing they know more than they do.

Why We Fall for Overconfidence

Overconfidence seduces because intuition feels right. Your judgments arrive fully formed, like gut instincts—whether it’s trusting a “sure thing” investment or believing your memory is flawless. Moore describes this as the illusion of knowing. Research on flashbulb memories (people recalling where they were during 9/11) shows how vividly wrong memories can feel. Everyone remembers details differently yet remains sure theirs are correct. This misplaced confidence underpins how we misjudge probabilities and act too boldly.

Confidence Gone Global: The 2008 Crisis

One of Moore’s most vivid examples is the subprime mortgage meltdown. Financial institutions created mortgage-backed securities based on mistaken certainty. Investors assumed historical data would predict future outcomes, ignoring that new NINJA (“no income, no job, no assets”) loans weren’t represented in models. As defaults skyrocketed to 50%, trillions were lost. Here, overprecision—being too sure of one’s numbers—fed catastrophic overplacement among bankers who thought they were smarter than everyone else. Moore shows that Chuck Prince’s infamous quote—“as long as the music’s playing, you’ve got to dance”—was overconfidence in action.

The Gateway Bias

Overconfidence doesn’t only cause errors—it amplifies all other biases. It’s the gateway drug of bad judgment. Once you’re sure you’re right, confirmation bias (seeking agreement) and availability bias (overweighting vivid examples) become stronger. Kahneman and Plous, whom Moore cites, considered overconfidence the most significant cognitive bias of all. Correcting it starts with humility based on evidence—asking, “How might I be wrong?”

The Emotional Cost

The aftermath of overconfidence isn’t just financial—it’s psychological. People suffer greater embarrassment, remorse, or resistance to feedback when reality disproves their beliefs. In business, this appears as overconfident CEOs—like Joe Cassano at AIG—who suppress dissent, turn meetings into echo chambers, and ignore warnings until collapse. In your own life, overconfidence can appear as believing deadlines don’t apply to you, investing beyond your knowledge, or assuming your moral compass is flawless. Each stems from certainty untested by truth.

“Appropriate humility about judgment is the antidote to disaster.” —Don A. Moore

Recognizing overconfidence as the root of bias isn’t about shame; it’s about calibration. Moore teaches that knowing you could be wrong is the first step to being right. It’s the difference between Elon Musk sleeping in his factory, chasing impossible goals despite repeated explosions, and a realist entrepreneur setting achievable dreams with evidence-based optimism. Perfect confidence doesn’t silence ambition—it grounds it in truth.

If overconfidence is a reckless leap, underconfidence is freezing at the edge. Moore argues that underconfidence causes just as much harm by deterring you from action, relationships, and growth. It’s the quiet bias that keeps talented people from applying to elite universities, asking for promotions, or sharing bold ideas.

The Fear of Not Being Enough

Moore exposes underconfidence through the stories of high achievers wracked with doubt. Thomas Jefferson believed “more confidence is placed in me than my qualifications merit.” Maya Angelou worried that someone would discover she’d “run a game on everybody.” Even accomplished writer John Steinbeck feared he wasn’t a real author. These confessions define impostor syndrome: feeling inadequate while being fully capable.

How Underconfidence Limits Potential

Moore cites psychologist Justin Kruger’s research showing that people underrate themselves at difficult tasks because they know their own incompetence but not others’. This creates false humility. Low-income students, for instance, often don’t apply to top colleges because they assume rejection, even though many receive full scholarships. Similarly, competent employees hesitate to volunteer for stretch assignments or negotiations, letting less capable but bolder peers advance.

The Mirror Image of Overconfidence

Ironically, the same mechanism that makes people think they’re more honest than others also makes them think they are worse at rare tasks. When you know your flaws intimately but can’t see others’, you assume they have fewer. Moore’s clever analogy—you know your naked body’s imperfections better than others’, but every body has flaws—captures how self-focus distorts comparison.

The Cost of Inaction

Underconfidence produces errors of inaction—declining opportunities that would have succeeded. It hides behind self-protection: “What if I fail?” “What if I’m embarrassed?” Moore reminds us that perfect confidence doesn’t mean assuming success; it means knowing the odds and acting when they favor you. In decision-making, he urges truth-based optimism, not delusion. For entrepreneurs, this means acknowledging the high failure rate (nearly 80% of startups fail) yet still pursuing calculated risks when expected value is positive.

The cure for underconfidence resembles the cure for overconfidence: feedback and evidence. You correct your biases not by pumping up self-esteem but by collecting reality checks. Moore’s lesson is simple but radical—confidence isn’t about feeling good; it’s about predicting accurately and acting accordingly.

You’ve probably felt sure you knew something—only to later find out you were wrong. Moore calls this gap between belief and reality the problem of miscalibration. Perfect confidence is achieved when beliefs, judgments, and outcomes align. Calibrating confidence requires structured thinking: specifying probabilities, assessing outcomes, and learning from feedback.

Probability Distributions vs. Point Predictions

Moore recounts how BASF, the world’s largest chemical producer, struggled with forecasting demand because it relied on “best guesses.” Managers predicted single numbers—100,000 kilograms of ibuprofen sold—rather than probability ranges. Predicting a fixed number is folly; reality unfolds across distributions. Moore teaches you to think like a statistician: consider low, medium, and high outcomes instead of giving one precise forecast. It’s better to imagine sales between 90,000 and 110,000, knowing extremes are possible.

Thinking in Expected Value

Expected value (probability multiplied by outcome) is Moore’s golden rule. He used it himself when his mentor, Max Bazerman, offered an amusing “insurance policy” on his PhD job prospects—pay $5,000 now for a guaranteed future salary if he failed to get hired. Calculating the expected value revealed it was too expensive to be worth buying, reinforcing his confidence realistically. Likewise, when Apple spent $100 million on the failed Newton, Moore shows that expected value justified it because the chance of success multiplied by potential payoff dwarfed the cost. Failures can have positive expected value if wisely taken.

Learning by Keeping Score

Calibration comes through feedback. Moore advises writing down predictions and checking them later to resist hindsight bias. Google uses postmortems for failed projects like Google Glass or Google+, asking: “What happened?” and “What can we do differently next time?” Individual calibration works similarly—make forecasts for your projects and compare actual results. Over time, you gain a sense of when your optimism or pessimism misleads you.

“Confidence calibration isn’t perfection—it’s progress toward truth.”

As Moore puts it, confidence calibration is difficult but transformative. When you express forecasts probabilistically—like “there’s a 60% chance I’ll finish in two weeks”—you accept uncertainty gracefully. Calibration doesn’t eliminate error; it teaches humility, better decisions, and wiser risk management. That’s what it means to be perfectly confident.

Moore insists that the simplest and most powerful debiasing technique is also the hardest to do: consider the opposite. Instead of asking why you are right, ask why you might be wrong. This reversal combats confirmation bias and overprecision by forcing you to think beyond your ego.

Testing Hypotheses Backward

Most minds search for supportive evidence. When Harold Camping predicted the apocalypse in 2011, his followers refused any bet that paid out after Judgment Day because they were sure the world would end. Economists who studied them—offering $5 now or more money later—found believers incapable of considering disconfirming evidence. Moore links this to Francis Bacon’s warning centuries earlier: people notice affirmatives but ignore negatives. The real test of truth is asking what would disprove your belief.

Learning from Disagreement

Constructive disagreement is the foundation of wisdom. Moore praises organizations like Amazon, which reward employees for “respectfully challenging decisions.” At UC Berkeley, tenure meetings begin with one speaker arguing for and another against—that’s formalized devil’s advocacy. Even Popes used the position of Promotor Fidei, the “Devil’s Advocate,” to prevent rash canonizations. Pope Sixtus V’s rule slowed saint-making for centuries, proving skepticism’s virtue.

The Gift of Critics

Critics can irritate you—but they are invaluable. Moore cites Senator Al Franken’s willingness to thank a staffer who called him out for arrogance. Leaders who invite constructive criticism build truth-centered organizations. Ignoring critics, whether you’re a CEO or a family decision maker, breeds blindness. The “bowels of Christ” quote from Oliver Cromwell—“I beseech you, think it possible you may be mistaken”—embodies this humility. Perfect confidence means seeing dissent as data, not defiance.

When disagreement arises, ask yourself: what evidence could prove me wrong? If you can name none, your belief may be faith, not fact. As Jeff Bezos told his managers, “People who are right a lot change their minds a lot.” That’s what perfect confidence looks like—courage to question yourself.

Moore shows that wise decision-makers forecast not only possibilities but failures. This dual vision—the postmortem and premortem mindset—builds resilience and prevents overconfident optimism. He illustrates with both real disasters and organizational triumphs.

Learning from Death (Postmortem Thinking)

The airline industry’s safety record—safer per mile than walking—exists because of rigorous postmortems. After every accident, investigators examine what failed. Boeing’s 737 Max crashes stemmed from ignored warnings about software flaws. When organizations perform honest postmortems, like Google analyzing failed projects, they increase their chances of avoiding repeat mistakes. The mantra “fail fast, fail often” embodies healthy humility.

Imagining Failure Before It Happens (Premortem Thinking)

Psychologist Gary Klein’s premortem asks teams to imagine that a project has failed spectacularly and list every reason why. Moore recounts one such meeting where someone dared to say aloud what others feared: if the CEO retired early, the project might collapse. Premortems reveal hidden dependencies and overconfidence risks. In Kahneman’s words, this technique “invites people to imagine the disaster and write its history.”

Defensive Pessimism and Disaster Preparedness

Defensive pessimists channel fear productively. Students who dread failing exams study harder. Similarly, leaders who imagine their company collapsing prepare better. Moore praises Warren Buffett and Charlie Munger’s philosophy: “Invert, always invert—tell me where I’ll die so I don’t go there.” Facebook’s Project Storm and Berkeley’s earthquake drills show how collective foresight prevents catastrophe. Vasily Arkhipov, the Soviet sailor who refused to launch a nuclear torpedo during the Cuban Missile Crisis, epitomizes this foresight—he literally saved the world by resisting panic.

“Better than learning from tragedy is avoiding it entirely.”

Perfect confidence merges caution with courage. By forecasting both success and failure, you make rational choices about risk. Moore’s blend of psychology, philosophy, and business strategy reframes failure as data—not defeat.

Moore introduces the logic of expected value as the foundation of wise decision-making. Every choice—whether buying insurance, launching a product, or going skydiving—has both probability and value. Multiply them, and you see what it’s really worth. Perfect confidence means applying math to emotions.

Wishful Thinking vs. Rational Betting

Moore’s stories—from Jerry Yang rejecting Microsoft’s $44 billion offer for Yahoo! to entrepreneurs bleeding confidence—show how desire can distort probability. Optimism feels good but often misleads. He humorously analyzes his own bet with Max Bazerman and demonstrates how risky choices look different once you quantify their odds. Rational optimism beats wishful thinking.

Taking the Right Risks

Citing Nobel laureate Paul Samuelson’s coin-flip study, Moore examines how people reject positive-value bets because losses hurt more than gains please—a bias Prospect Theory calls “loss aversion.” He teaches you to overcome fear of small losses by adopting a policy mindset: take every worthwhile bet, knowing the law of large numbers will favor you over time. Investing, eating healthily, or engaging socially all follow this rule. Everyday gambles add up to a life of rational courage.

Keeping Score and Avoiding Hindsight Bias

Tracking expected values guards against regret and hindsight bias. Successful innovators like Jeff Bezos and Elon Musk justify bold projects not because they’re sure they’ll win but because the payoff outweighs the risk. Amazon’s model, Moore argues, treats every experiment as a bet on expected value. Failures like Apple’s Newton or Boeing’s rushed 737 software remind us that ignoring probabilities leads to ruin.

Applied to personal life, this method transforms choices—careers, relationships, even parenting—into informed wagers. It’s not cynicism; it’s grounded hope. As Moore says, sound confidence isn’t pretending you’ll never lose—it’s knowing you’ll win more than you’ll lose, on average.

In his closing chapters, Moore connects psychology with philosophy. Perfect confidence, he writes, is not extreme—it’s the middle way. Borrowing from Aristotle, Buddhism, and Theodore Roosevelt, Moore concludes that happiness and success grow when confidence matches truth.

Evidence-Based Courage

Moore’s examples of Alex Honnold, the free-solo climber who ascended Yosemite’s 3,000-foot El Capitan without ropes, demonstrate the balance between fear and mastery. Honnold’s confidence wasn’t bravado; it was earned through data—every move rehearsed until certainty was rational. Overconfident climbers die from recklessness; underconfident ones exhaust themselves clinging too tightly. The same principle applies to life’s climbs: pursue difficult goals only after preparing enough to justify belief.

Overconfidence vs. Underconfidence Revisited

Moore compares overconfidence to false positives and underconfidence to false negatives. Sometimes, errors of excess are worse—as when engineers in Genoa trusted a bridge’s concrete too much, allowing deadly collapse. Other times, excess caution wastes opportunity. The point: don’t ask which side is better; seek the truth. Perfect confidence is accuracy plus courage.

Feeling Good About the Facts

Moore ends on an uplifting note. Seeing truth doesn’t mean being pessimistic; it means choosing gratitude. He invites you to imagine downward counterfactuals—how much worse things could be—to appreciate how good they are. Modern life, he reminds us, is astonishingly prosperous compared to the past. The goal isn’t false hope; it’s joyful realism.

“Believe the truth. Act boldly when odds favor you, and with humility when they don’t.”

Between arrogance and fear lies wisdom. Perfect confidence is not the loudest voice—it’s the truest one. Calibrate your beliefs, learn from evidence, welcome correction, and savor the chances worth taking. That’s how confidence becomes perfect.