How I think I think

‘I know you want me to force myself to think in black and white but I won’t.’ — Antonia

People taking multiple comparable decisions every day tend to create mental models to operate more efficiently. I suspect these are widely used in sports, politics, videogames, war, and Tinder. Venture capital has forced me to create and apply different mental models to quickly evaluate a deck or weigh a founding team.


These systems may also help solve more complex puzzles. Marc Andreessen, for example, says he has a mental model of a tiny Peter Thiel sitting on his shoulder. He discusses tough problems with his mini peer who helps him ponder difficult issues. I’ve realized that once I go beyond the quick decision and face an important choice, my pendulum mental model kicks in.


When I activate this framework, a massive bob hanging from a pendulum is already oscillating, sometimes forcefully between the two sides of an important decision. In order to reach a conclusion, I go from yes to no, and no to yes, several times during a process that can take a few weeks. Data acts like a gravity force that propels the bob back to equilibrium where I can finally see my decision. As the process moves on, one of the opposite positions becomes more dominant.


What makes this process unpredictable is that new information can disrupt the bob back to big movements. When gathering information or seeking opinions I may be on an extreme side of the pendulum, testing black or white. If I see gray, I use that to validate black or white. During the entire process, my positions are, in general, extreme but weakly held.


Most sensible people including my extremely bright partners work with shades of gray that they feed with new information to uncover the truth. Since most important decisions in our business are binary — to invest or not invest — sensible investors use their final position on a grayscale to resolve whether to go black or white.


In my head, when the bob of the pendulum finally stands still, I find conviction.

This is by no means an optimal decision process. It comes not from a deliberate settlement but from an impaired and hyperactive brain. To be honest, it’s exhausting. I’m sure it’s confusing for people around me too. But that’s what’s makes me, me. And, that’s ok.

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