”I have what I call an iron prescription that helps me keep sane when I naturally drift toward preferring one ideology over another and that is: I say that I’m not entitled to have an opinion on this subject unless I can state the argument against my position better than the people who support it. I think only when I’ve reached that state am I qualified to speak.”

The above quote is from Charlie Munger, Warren Buffett’s right-hand man for more than 40 years, and it offers wonderful advice for anyone wishing to stay open to the importance of—as well as the need for—unlearning.

Munger’s practice of arguing opposite sides of an issue is a practice that dates back thousands of years. As Nassim Taleb recounts in his wonderful book, Fooled by Randomness, in 155 B.C. the Greek philosopher, Carneades, traveled to Rome to argue against a fine which had been levied upon the Athenians.

With unmatched eloquence, Carneades sang the praises of Roman justice and convincingly swayed his audience to the merits of his position. Alas, that was not the point he was trying to make. The very next day Carneades dissected his previous arguments and proceeded to persuasively convince the same audience that the opposite was true.

So where did Carneades really stand on the issue? We don’t know. But that doesn’t matter because what he wanted to advocate was a doctrine of ‘uncertainty of knowledge.” Carneades, you see, was a “radical skeptic” and believed that all knowledge is impossible to know, except for the knowledge that all knowledge is impossible. Or, as Taleb writes, “[h]e stood all his life against arrogant dogma and belief in one sole truth.”

Carneades, though, recognized he lived in the real world and realized such a philosophy would not be readily accepted—or easily tolerated—by a society in need of rules and structure. He, therefore, advocated the idea that “probabilities of truth” could be established, and that these probabilities of truth might reasonably guide society.

The philosophy calls to mind a quote from F. Scott Fitzgerald who once said: “The test of a first rate mind is the ability to hold two diametrically opposed ideas at the same time and still function.”

The ability to deal with ambiguity is not, however, a luxury reserved only for ancient philosophers and poets. In 1988, a study by the American Management Association found that the leadership characteristic most essential for steering organizations through troubled and complex times was “the ability to deal with ambiguity.”

One strategy for preparing for such ambiguity is, like Carneades, to know the opposing side of an argument was well as the supporting arguments. In this way, whenever new—and perhaps contradictory information—becomes available, the holder of the opinion (or position) can assimilate that information into their decision-making process. This, in turn, might make it easier to reverse a position in spite of having voiced support for it in the past. Why might this be so? Because the previous work in understanding the opposite view will have tilled and loosened the soil in which unlearning may take place.