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A good decision can still have a bad outcome. The key is to focus on a strong process for the decision itself. Afterward, all energy should shift from relitigating the choice to proactively managing the new circumstances to create the best possible outcome.
Regularly re-evaluate your investment theses. Stubbornly holding onto an initial belief despite new, contradictory information can lead to significant losses. This framework encourages adaptation by forcing you to re-earn your conviction at regular intervals, preventing belief calcification.
An investor might correctly identify a company's flaw but still be wrong to pass, as great founders often fix those issues. This requires investors to have the humility to admit their ultimate conclusion was wrong, even if their initial analysis was correct, and be willing to re-engage with the startup.
Obsessing over whether past decisions were 'right' is paralyzing and wasteful. Accept that you made the best call with the data available at the time and move on. The speed gained from this mindset allows you to make more total decisions, leading to a net win.
Individual project failures are insignificant when viewed within the context of a larger life purpose. A single wrong strategic decision doesn't cripple you because success is a 'net-net game.' Focus on your overall trajectory and process, not isolated outcomes.
In high-stakes leadership roles, the paralysis of indecision often causes more damage than a suboptimal choice. Making a poor decision allows for feedback, correction, and continued momentum, whereas inaction leads to stagnation and missed opportunities. The key is to decide, learn, and iterate quickly.
To avoid emotional, performance-chasing mistakes, write down your selling criteria in advance and intentionally exclude recent performance from the list. This forces a focus on more rational reasons, such as a broken investment thesis, manager changes, excessive fees, or shifting personal goals, thereby preventing reactionary decisions based on market noise.
Don't focus on making perfect decisions upfront. Instead, cultivate the ability to quickly reverse a bad decision once you recognize it. The inability to tolerate a known bad situation allows you to cut losses and redeploy resources faster than those paralyzed by fear or sunk costs.
Every mistake unfolds in three acts: 1) the development of your underlying mental models, 2) the mistaken decision itself, and 3) the aftermath and how you process it. Many people focus only on Act 2 (the mistake), but the most damaging error is often made in Act 3 by failing to unpack and learn from the experience.
Citing former Treasury Secretary Bob Rubin, Josh Steiner argues you should never judge a decision by its outcome. A bad process can get lucky, and a rigorous one can fail. The key is to run a process that gathers all available information and empowers experts. Once that decision is made, don't look back, regardless of the result.
Evaluate every check, including follow-on investments, independently from prior commitments. The decision should be based solely on the current risk-adjusted value of that capital, not on past investments, which prevents throwing good money after bad.