16th-century philosopher Montaigne collected bizarre foreign customs (e.g., blackening teeth) not for novelty, but to remind himself how arbitrary his own cultural norms were. This practice helps leaders and investors question their own deeply ingrained, "obvious" truths and see reality from a new perspective.
Genius, whether in comedy, investing, or leadership, is the art of noticing. It's about being more sensitive to details, questioning foundational assumptions (like why slavery ended), and seeing the opportunity in things others accept at face value. This is a trainable skill of curiosity.
When thrust into unfamiliar or intimidating settings, pretending to be an anthropologist can dissolve imposter syndrome. This mental shift reframes the situation from a personal performance test into a field study. It transforms discomfort into curiosity, allowing you to observe, take mental notes, and feel like you belong.
To accurately assess a leader's actions, especially an unconventional one, avoid asking 'What would it mean if I did that?' Instead, ask 'What does it mean that *they* are doing that?' This helps separate your personal behavioral standards from their actual intent and worldview.
To combat self-deception, write down specific predictions about politics, the economy, or your life and review them 6-12 months later. This provides an objective measure of your judgment, forcing you to analyze where you were wrong and adjust the thought patterns that led to the incorrect forecast.
Barry Diller's key lesson from failure is that experience breeds cynicism, which corrupts good decision-making. He advises leaders to constantly fight this tendency and "scrub their instincts clean." Maintaining a degree of naivete is crucial for accurately judging new ideas without being biased by past negative experiences.
Guidara deliberately avoided hiring people with extensive fine-dining experience. Newcomers are less beholden to industry norms and more likely to ask "why," challenging long-held assumptions. This 'intelligent naivety' can be a superpower for innovation, preventing stagnation.
Open-mindedness is not a passive virtue but a competitive advantage. "Strategic tolerance" is the deliberate act of engaging with opposing views and information you dislike. This process pressure-tests your own ideas against reality, making you and your business strategies more resilient and effective.
Our brains are wired to find evidence that supports our existing beliefs. To counteract this dangerous bias in investing, actively search for dissenting opinions and information that challenge your thesis. A crucial question to ask is, 'What would need to happen for me to be wrong about this investment?'
No matter how intelligent you are, personal bias clouds judgment. For all significant decisions—personal, professional, or economic—consult a trusted "kitchen cabinet" of objective advisors. This external perspective is crucial for sound decision-making and protects against isolated thinking.
To counteract the brain's tendency to preserve existing conclusions, Charles Darwin deliberately considered evidence that contradicted his hypotheses. He was most rigorous when he felt most confident in an idea—a powerful, counterintuitive method for maintaining objectivity and avoiding confirmation bias.