There are a class of occupations where the job of the worker is to know and anticipate the unknown unknowns of a situation or domain.
Aircraft safety engineers and investigators, for example, are tasked with anticipating emergency situations or failure modes of complex machines (aircrafts) that we might not have discovered to even be possible yet. Because commercial airliners are engineered to such rigorous standards of safety (exceptions like the 737 MAX notwithstanding), most aviation accidents these days are caused by failure modes that previously were not even considered in the design process, like multiple engines or safety backups failing, fueling mistakes, or miscommunication during takeoff and landing between planes on the runway. The job of safety engineers and investigators is to consider these unknown unknowns.
Venture investors are also tasked with understanding unknown unknowns. In early stage venture, the market is usually saturated with business ideas that are certain to succeed already, and the founders that seek investments are working on ideas that aren’t obviously right. The job of the early-stage investor then is to ask, “what do these founders know that everyone else in this space doesn’t?” They are looking for unknown unknowns, the answers to questions everyone else in the market is not yet asking.
Cryptographers are also quite adept at this challenge. The mathematics that underlie modern cryptography is often provably safe. The main challenge of cryptography engineers is not necessarily to prove or disprove the correctness of mathematics that underlie cryptosystems, but to anticipate ways that factors outside mathematics can compromise the guarantees of an implementation of a cryptographic algorithm. Common attacks on modern cryptosystems are often “side-channel” attacks, things like abusing the speed of computation, exploiting certain details of the hardware executing the code, or even using sounds and radio waves emitted by electronics executing secure code to leak secret information. The job of a cryptography engineer is to anticipate these unknown unknowns, and ask questions about factors that nobody else is asking to assess whether a cryptosystem is secure enough for a particular use case.
Jobs that are about anticipating unknown unknowns are often “professional question-askers”. Their main task is exploration and learning, constantly. Their job is probably the most immune to automation, because their work is already mostly about continually making themselves obsolete, and finding new problems to solve.
I’m curious what similarities are shared between people who thrive in these kinds of jobs.