The Three Sides of Risk · Collaborative Fund
Carl Richards writes: “Risk is what’s left over when you think you’ve thought of everything.”
Morgan Housel • The Psychology of Money: Timeless lessons on wealth, greed, and happiness
Instead of pursuing options that cap downside while also capping upside, make bets that have asymmetric pay-offs: If you win, you win big. If not, you’ve gained valuable skills, relationships, and reputational benefits that will carry you over to your next asymmetric bet.
Erik Torenberg • Reconsidering Career Optionality
Too often our efforts to manage risk create further risks. Whether in combat or in day-to-day life, we encounter situations that call for us to assume a reasonable amount of risk to achieve our goals, and if we try to make ourselves “bulletproof,” we may ultimately collapse under the weight of our gear.
Stanley McChrystal • Risk
If we had a magic wand we would find out exactly what proportion of these outcomes were caused by actions that are repeatable, versus the role of random risk and luck that swayed those actions one way or the other. But we don’t have a magic wand. We have brains that prefer easy answers without much appetite for nuance. So identifying the traits we
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