Simply keeping pace with peers is not a valid measure of success. If peers are taking excessive risks in a bubble, matching their performance means you were equally foolish. True skill is outperforming in bad times while keeping pace in good times.

Instead of succumbing to the "Fear of Missing Out," top investors deliberately practice "Thoughtfully Missing Out." This means consciously deciding not to pursue trendy investments that fall outside their clearly defined circle of competence, which prevents costly mistakes.

The worst feeling for an investor is not missing a successful deal they didn't understand, but investing against their own judgment in a company that ultimately fails. This emotional cost of violating one's own conviction outweighs the FOMO of passing on a hot deal.

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.

To achieve above-average investment returns, one cannot simply follow the crowd. True alpha comes from contrarian thinking—making investments that conventional wisdom deems wrong. Rubenstein notes the primary barrier is psychological: overcoming the innate human desire to be liked and the fear of being told you're 'stupid' by your peers.

The difficulty in going against conventional wisdom isn't just intellectual. According to David Rubenstein, it's rooted in the human desire to be liked and respected. People avoid contrarian bets because they don't want to be told they're "stupid" by their peers, making the psychological and social cost very high.

Junior investors often seek external validation. A better approach is to study successful investors to build a strong internal instinct for what greatness looks like. Once developed, you must trust this instinct and back your non-consensus ideas with confidence, as seeking consensus or borrowing conviction is a critical mistake in venture.

Copying a guru's strategy often fails. Their outperformance might be a temporary style factor, not just skill. More importantly, their unique circle of competence is not transferable. Focus on becoming a better version of yourself, not a second-rate version of someone else.

Mala Gaonkar combats investment fads by replacing the "Fear of Missing Out" (FOMO) with "Thoughtfully Missing Out" (TOMO). This framework encourages her team to consciously and deliberately pass on hyped opportunities that fall outside their defined circle of competence, avoiding costly mistakes.