Instead of waiting for obvious failure, "anomalizing" involves proactively looking for small, early signs that reality is departing from your expectations. This mental habit allows for early course correction before a mistake becomes costly.

Contrary to 'positive thinking,' this method involves identifying everything that could go wrong for each step required to succeed. By proactively creating solutions for these risks, you significantly increase your overall probability of success and de-risk your goals.

A pre-mortem asks a team to imagine their project has already failed spectacularly. By explaining the hypothetical failure, they uncover potential risks and can build mitigation strategies, effectively using the power of hindsight bias in advance.

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.

Instead of waiting for a postmortem after failing, conduct a 'premortem' at the start. Proactively contemplating the specific obstacles that might prevent you from achieving your goals is a critical first step. This pessimistic-sounding exercise allows you to identify barriers like impulsivity or laziness and design solutions for them.

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?'

AI models tend to be overly optimistic. To get a balanced market analysis, explicitly instruct AI research tools like Perplexity to act as a "devil's advocate." This helps uncover risks, challenge assumptions, and makes it easier for product managers to say "no" to weak ideas quickly.

Before committing capital, professional investors rigorously challenge their own assumptions. They actively ask, "If I'm wrong, why?" This process of stress-testing an idea helps avoid costly mistakes and strengthens the final thesis.

Before starting a project, ask the team to imagine it has failed and write a story explaining why. This exercise in 'time travel' bypasses optimism bias and surfaces critical operational risks, resource gaps, and flawed assumptions that would otherwise be missed until it's too late.