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Navigating ambiguity. | Irrational Exuberance

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Perceiving the layers of context in problems will unlock another stage of career progression as a Staff-plus engineer, but there’s at least one essential skill to develop afterwards: navigating ambiguity. In my experience, navigating deeply ambiguous problems is the rarest skill in engineers, and doing it well is a rarity. It’s sufficiently rare that many executives can’t do it well either, although I do believe that all long-term successful executives find at least one toolkit for these kinds of problems. Before going further, let’s get a bit less abstract by identifying a few examples of the kinds of problems I’m referring with the label deeply ambiguous: At Stripe, we knew that data locality laws were almost certainly coming, but we didn’t know when or what shape that regulation would come in. One scenario was that many countries would require domestic transactions (e.g. transactions where the buyer and seller reside in the same jurisdiction) to be stored in a domestic datacenter, w

Perceiving the layers of context in problems will unlock another stage of career progression as a Staff-plus engineer, but there’s at least one essential skill to develop afterwards: navigating ambiguity. In my experience, navigating deeply ambiguous problems is the rarest skill in engineers, and doing it well is a rarity. It’s sufficiently rare that many executives can’t do it well either, although I do believe that all long-term successful executives find at least one toolkit for these kinds of problems. Before going further, let’s get a bit less abstract by identifying a few examples of the

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