False dichotomies are undisciplined thought. In the words of F. Scott Fitzgerald, “The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.” Builders of greatness are comfortable with paradox. They don’t oppress themselves with what we call the “Tyranny of the OR,” which pushes people to believe that things must be either A OR B, but not both. Instead, they liberate themselves with the “Genius of the AND.” Undisciplined thinkers force debates into stark “Tyranny of the OR” choices; disciplined thinkers expand the conversation to create Genius of the AND solutions.

Because the process of achieving high-level objectives is necessarily iterative in this sense, the path to these objectives is bound to be oblique.

When you cannot measure something, said Lord Kelvin, ‘your knowledge is of a meager and unsatisfactory kind’.

In chapter 7 I described a spectrum of problems. At one end were those— like nought and crosses— best solved directly; at the other were those— the pursuit of happiness— best achieved obliquely. There is an analogous spectrum of decision-making styles, from direct to oblique.

The direct decision maker perceives a direct connection between intentions and outcomes; the oblique decision maker believes that the intention is neither necessary nor sufficient to secure the outcome. The direct problem solver reviews all possible outcomes; the oblique problem solver assembles all available information; the oblique decision maker recognises the limits of his or her knowledge. The direct decision maker maximises his or her objectives; the oblique decision maker is continuously adaptive. The direct problem solver can always find an explanation for his or her choices; the oblique problem solver sometimes just finds the right answer. The direct decision maker believes that order is the production of a directing mind; the oblique decision maker recognises that order often emerges spontaneously— no one fully grasps it. The direct problem solver insists on consistency, on always treating the same problem in the same way; the oblique problem solver never encounters exactly the same problem twice. The direct decision maker emphasises the importance of rationality of process; the oblique decision maker believes that decision making is inherently subjective and prefers to emphasise good judgment.

The intelligence agents who anticipated the attack on the Twin Towers were not praised for their prescience, and the risk managers who warned banks of impending nemesis were fired. It is good for reputation to succeed against the odds. But it is often better for reputation to fail against the odds than to improve them. In an uncertain situation the effect of improving the odds is never obvious, either before the event or after it.

Captain MacWhirr, limited man though he was, understood that dilemma. Machiavelli, the epitome of the oblique decision maker, was the archetypal fox. Five centuries before Tetlock confirmed it empirically, Machiavelli understood that to be an effective decision maker it was wise not to seek public credit for the success of your decisions. Yet another of obliquity’s many paradoxes.

I asked, “If you could pick one trait that would predict how someone would turn out, what would it be?”

“That’s easy,” he said. “How willing they are to change their mind about what they think they know.”

The most valuable people, he continued, weren’t the ones with the best initial ideas, but the ones with the ability to quickly change their minds. They were focused on outcome over ego. By contrast, he said, the people most likely to fail were those obsessed with minute details that supported their point of view.