A study highlighted by Michael Lewis found men systematically overestimate their knowledge, while women underestimate theirs. This cognitive bias is a major risk in investing and leadership. The anecdote of a man confidently miscorrecting "Marie Curie" to "Mariah Carey" perfectly illustrates this dangerous self-assurance.
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Women and people of color often believe they need another certification to be qualified, while men confidently pursue roles with fewer prerequisites. This highlights a systemic confidence and perception gap, not a competence gap, where women over-prepare to compensate for perceived shortcomings.
Howard Marks argues that declaring uncertainty is a sign of strength, not weakness. In important settings, saying "I don't know" signals that your ego is in check and thinking is robust. It makes people trust you more, not less, because it shows intellectual humility.
Post-mortems of bad investments reveal the cause is never a calculation error but always a psychological bias or emotional trap. Sequoia catalogs ~40 of these, including failing to separate the emotional 'thrill of the chase' from the clinical, objective assessment required for sound decision-making.
Don't conflate confidence with self-assurance, which is the *accurate* assessment of one's skills. Many top performers downplay their expertise out of a false sense of humility. This incongruence can be misinterpreted by others as manipulation, confusion, or a risky inability to self-assess.
The more people learn about a subject, the more they realize how much they don't know. This contradicts the idea that expertise leads to arrogance. Novices, who are unaware of a field's complexity, are often the most overconfident.
True self-awareness involves publicly admitting your weaknesses. By openly stating what you're bad at (e.g., 'I suck at 99% of things'), you build immense credibility and trust when you then declare your strengths. This approach validates your expertise in your core competencies.
True growth and access to high-level opportunities come not from feigning knowledge, but from openly admitting ignorance. This vulnerability invites mentorship and opens doors to conversations where real learning occurs, especially in complex fields like investing, which may otherwise seem like a "scam."
In 2008, Howard Marks invested billions with conviction while markets crashed, yet he wasn't certain of the outcome. He held the paradox of needing to act decisively against the crowd while simultaneously accepting the real possibility of being wrong. This mental balance is crucial for high-stakes decisions.
The self-doubt often felt by high-achievers isn't a debilitating flaw. It can motivate leaders to over-prepare, seek diverse expert opinions, and ultimately make more informed decisions, turning a perceived weakness into a strength.
Charlie Munger's comment on Elon Musk—"Never underestimate the man who overestimates himself"—highlights a paradox. Extreme self-belief, often a flaw, can be a founder's greatest asset, fueling the audacity required to pursue goals that rational minds dismiss as impossible.
