Jeff Aronson warns that prolonged success breeds dangerous overconfidence. When an investor is on a hot streak and feels they can do no wrong, their perception of risk becomes warped. This psychological shift, where they think "I must be good," is precisely when underlying risk is escalating, not diminishing.

In a rising market, the investors taking the most risk generate the highest returns, making them appear brilliant. However, this same aggression ensures they will be hurt the most when the market turns. This dynamic creates a powerful incentive to increase risk-taking, often just before a downturn.

During periods of intense market euphoria, investors with experience of past downturns are at a disadvantage. Their knowledge of how bubbles burst makes them cautious, causing them to underperform those who have only seen markets rebound, reinforcing a dangerous cycle of overconfidence.

Investors often underestimate how easily years of compounded gains can be erased by a single bad decision, such as using excess leverage or making an emotional choice. Downside protection is not merely a defensive strategy; it's a vital, offensive component for ensuring the compounding engine survives to continue running.

Conventional definitions of risk, like volatility, are flawed. True risk is an event you did not anticipate that forces you to abandon your strategy at a bad time. Foreseeable events, like a 50% market crash, are not risks but rather expected parts of the market cycle that a robust strategy should be built to withstand.

Experienced pilots crashed a perfectly flyable plane because overwhelming alarms caused their executive function to collapse. They fixated on one wrong idea, ignoring contradictory data—a stark warning for investors in volatile markets.

AI can quickly find data in financial reports but can't replicate an expert's ability to see crucial connections and second-order effects. This leads investors to a false sense of security, relying on a tool that provides information without the wisdom to interpret it correctly.

After nearly crashing his plane by abandoning his flight plan on a whim, Jim Clayton learned a critical lesson: in high-stress situations, your senses can be wrong. He applied this to business, relying on data and strategic plans over impulsive emotional reactions during predicaments.

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?'