If You’re Sure You’re Right (About Complicated Political or Policy Stuff), I’m Sure You’re Wrong

And That’s the Only Thing I’m Sure Of

“Positive; adj. = Mistaken at the top of one’s voice.”

Ambrose Bierce, the Devil’s Dictionary

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Photo by Robert Clark on Unsplash

Life is said to be a mystery wrapped in a riddle, not to mention the enigma. Maybe that’s why I feel less and less certain about anything with each passing day, and more and more at ease with uncertainty most of the time. Is that wisdom? Is that folly? Or is that the simple passage of time?

But there’s one clear exception to this rule. There’s one thing I feel paradoxically certain about; namely, that certainty itself is suspect. Not only that, in certain cases certainty is inherently wrong.

Philosophers of perception underscore the challenge, if not the impossibility, of seeing the world “as it is.” For one, our only direct field of vision on to the world is the microscopic realm of our own personal experience. And even that narrow slice is skewed by our perspective, subjectivity, and practical needs. Certain “natural” facts may exist irrespective of us—the hard ground beneath our feet, the big blue ocean, the chemical reaction that results from mixing baking soda with vinegar, etc. But political reality is a different beast entirely. It is the essence of a social construction.

In building this structure, we depend almost entirely on the reports of trusted (if not necessarily trustworthy) others, who often lead us astray whether they mean to or not.¹ A near infinite variety of elements—a combination of known factors, known unknowns, and unknown unknowns—enter into this construction. To name a few: The contrasting perspectives and conflicting interests of the different players involved; the distinct levels of consciousness they reflect and the modes of communication they deploy; the ever shifting contexts of evolving events and the unpredictable actions of individual people and groups within them. The international order itself can crumble, rearrange itself, transform. The kaleidoscope list goes on.

If even mathematics cannot provide definitive answers all the time—the exact value of PI, the precise quantity of infinity—human questions, which lack clear definition or well-defined parameters, are something else entirely. Certainty in connection with complicated issues of politics, foreign policy, or international affairs—say, predicting the results of our national elections, responsibility for resurgent violence in the Israel-Palestine conflict, or the deeper reasons for Russia’s invasion of Ukraine—is patently absurd.

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I spent the latter part of my diplomatic career obsessed with the idea of inevitable error in foreign policy. The high-impact strategic mistakes that were made during my time in service, including the invasion of Iraq (by most accounts, a quintessential unforced error), may be one reason. How did this happen? One answer: strategy may be guided by something other than rational calculation or national interests. Say for example (and Thucydides would), fear, or its exploitation by canny politicos. After all, 9/11 marked a clear before and after.

Another broader, perhaps better answer: In facing complicated questions of policy or strategy, no approach is ever foolproof or cost-free. Or can ever be. No approach is ever perfect. There is no right or wrong, good or bad, wise or stupid option in such matters—or at least not clearly and categorically so. And, if so, not very often. There is only better or worse, depending. The question becomes not which option is good, true or right but rather which collection or configuration of consequences, which variation of mixed bag results, which kinds or categories of error we are willing to embrace or endure. In that sense, in response to the jeering of critics about the mistakes we made on issue X, Y or Z (even when I quietly sympathize or agree with their assumptions), I’m always tempted to respond. “OK, tell me which mistakes, which nasty consequences, which different little shop of horrors you would have preferred to see. And please, be specific.”

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Early in the pages of his famous Personal Memoirs, Ulysses S. Grant captures this idea perfectly. Writing about the Mexican-American War, he recalls the many difficult obstacles encountered by American troops during their “southern route” approach to Mexico City. He then speculates that the “northern route… would have been the better one to have taken.” But he pulls back before plunging head over heels down the garden path of would of, could of, should of: “But my later experience has taught me two lessons: first, that things are seen plainer after the events have occurred; second, that the most confident critics are generally those who know the least about the matter criticized.”

Talk about skewering the target. How better to explain recent campus protests of the horrific violence in the labyrinthine maze of Israel-Palestine? Apart from understandable passion, I always felt these protests reflected the supreme confidence of those who knew very little. At a minimum, I thought, one should approach the issue with appropriate respect for its complexity, the different perspectives and layers—past and present—in play. For starters, shouldn’t the fact that Hamas fighters deliberately embed themselves in hospitals, schools and mosques be an equal focus of the justified outrage about massive civilian casualties? What about the horrific October 7 attack? I’m not saying don’t take a side. I’m not saying there isn’t blame to go around. I’m not trying to justify the conditions in Gaza or the (by all accounts cynical) ulterior aims of the Israeli government’s far right coalition. I’m only saying enter this labyrinth with caution and humility, with a mind open to its near paralyzing complexity. Many smart people with deep knowledge and long experience have tried to take on this most wicked of wicked problems, and come out of their agony with precious little to show for it. What makes anyone else so sure they know better? How exactly might they have responded had they been in charge? At what cost?

It’s rarely the substance or content of the opinion that gets under my skin (though it can be), it’s the certainty and stridency of its expression—a sure-fire indication (in my humble view) that they are wrong. Confidence in such cases sounds more like overconfidence to me, like being mistaken at the top of one’s voice.

Not to put too tautological a point on it, but things that are unknowable are impossible to know. The great Prussian theorist of war Carl Von Clausewitz cites the pivotal role played by chance—the so-called “fog” of war—in human affairs. You don’t know what will happen because you can’t know. Chance rolls the dice. The messenger misinterprets the command, and goes right instead of left. The candidate unexpectedly turns his head, and the assassin’s bullet nicks only his ear. The autocrat toys with a secret plan deep in the dark dungeon of his unbeautiful mind. Nobody else knows.

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I have read numerous accounts since November 5 of citizens entering the voting booth with one (wavering) intention in mind and emerging having voted a different way. It turns out they didn’t even know themselves what they would do. How can you?

That some critics claim (implicitly) to know the mind of Vladimir Putin strikes me as doubly preposterous for this very reason. (Does Putin himself know?) With perplexing certainty, they tell us that we in the West forced Putin’s hand. By allowing NATO to expand, by cornering Russia with our support for neighboring Ukraine, we provoked him to lash out in justified self-defense. I see. Well, that’s certainly one possibility. As philosophers know, the fact that an event actually occurred means that it was possible for it to occur in just that way. We can see that plainly now, in retrospect.

But did we see it the same way in the fog of the moment, before anything broke one way or the other, before the thing assumed a definitive shape? I don’t think so. This is confirmed by reviewing the historical record and replaying the vigorous debate that took place at the time. It was a classic “split memo” situation, with well-informed, thoughtful, intelligent people firmly entrenched on both sides. It certainly was no “slam dunk” in either direction. Nor is it clear now that we would have been better off taking the “northern route,” choosing option A instead of B. What if NATO had frozen its membership at the moment of Germany’s reunification? What if the West had rejected the appeals of former Eastern bloc countries for NATO protection against the risk of Russia's resurgent imperial ambition? Would Russia have paid forward the magnanimous gesture in kind, and chosen to respect the new sovereignty of its (vulnerable and unprotected) near abroad neighbors into the indefinite future, as history makes clear—irony intended—it would?

I leave the obvious counterfactual to the imagination. We may yet have the opportunity to test the hypothesis before long.

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It’s tempting to use the clear lessons of the past to illuminate our path to an uncertain future. More specifically, it is tempting to pull out elements of a past made plain in retrospect to guide our way through the fog of the present toward an unknowable future. Since a certain approach appeared to work before, the lesson seems to go, we can be confident it will work the same way again now. In a recent interview with the Economist podcast Checks and Balance, renowned speechwriter for Republican presidents and Wall Street Journal columnist Peggy Noonan worries that the world (and our fiercest rivals) are better prepared for our once and future president this time around, and thus what worked for him before might not work so well again. In that and other senses, critical elements of the complicated context have changed in known and unknown ways. We are back to starting at “Go”, but this time lured by a false knowledge at a time of deepening precariousness. What consequence might flow from being too certain this time around?

In the closing paragraph of the introduction to his master work on Diplomacy, Henry Kissinger lays out the difference in perspectives between the analyst and the statesman (whatever else one might say about the man, he knew both perspectives well): “The analyst runs no risk. If his conclusions prove wrong, he can write another treatise. The statesman is permitted only one guess; his mistakes are irretrievable. The analyst has available to him all the facts; he will be judged on his intellectual power. The statesman must act on assessments that cannot be proved at the time he is making them; he will be judged by history on the basis of how wisely he managed the inevitable change and, above all, how well he preserved the peace.” We’re about to get a test case of this familiar problem—the interplay of certainty and uncertainty, action and reaction, the all-knowing critic and the harried, hurried, highly distracted and woefully ignorant person in the arena, again.

1. In his brilliant Substack Newsletter Conspicuous Cognition, the philosopher Dan Williams writes about questions of perception in a nuanced, engaging, and refreshingly accessible way.