This post examines the virtue of wisdom. It is meant mostly as an exploration of what other people have learned about this virtue, rather than as me expressing my own opinions about it, though I’ve been selective about what I found interesting or credible, according to my own inclinations. I wrote this not as an expert on the topic, but as someone who wants to learn more about it. I hope it will be helpful to people who want to know more about this virtue and how to nurture it.

Singing the praises of wisdom at LessWrong has a bringing coals to Newcastle feel to it. After all, isn’t this community all about working hard and passionately to hack through the jungle of bias, illusion, and ignorance in search of the hidden temple of Athena?

So I was tempted to skip over wisdom and work on writing up some other virtue instead. But I’m hoping that by exploring wisdom as-a-virtue I can illuminate some facets of it that otherwise receive less attention here.

Two varieties of wisdom

There are two senses of wisdom that are found in some virtue traditions:

  1. phrónēsis, or “practical wisdom” (sometimes translated “prudence”), which concerns knowing how the world works, and reasoning well about how to pursue goals effectively (and about which goals are worth pursuing — which sometimes gets separated out into “conative wisdom”)
  2. philosophy, which concerns a more big-picture understanding of “what it’s all about,” whether or not there seems to be any way to make practical use of that understanding

They are both important: Phrónēsis without philosophy can make you merely clever; while without phrónēsis, philosophy can leave you with your head in the clouds, unable to bring your wisdom down to earth where you can make it matter.

“The title wise is, for the most part, falsely applied. How can one be a wise man, if he does not know any better how to live than other men? — if he is only more cunning and intellectually subtle?” ―Thoreau

Philosophy is also sometimes considered an important end in itself. Aristotle thought it was the richest and most satisfying activity for people to engage in, and reasoned that it was the pastime of the gods.

The person with the virtue of wisdom habitually and regularly prioritizes thinking and behaving wisely. Which raises the question: why wouldn’t you? You might at first think that the only reason why you would deliberately think or behave unwisely is because you believe mistakenly that you are being wise.

That is one way you can go astray: you might understand the wise course of action based on the sort of situation you are in, but mistakenly believe you are in some other sort of situation; or vice-versa, you might understand the situation you are in well enough, but be mistaken about how to confront situations of that sort wisely. But people are also deflected from wisdom by being overwhelmed by emotions like fear or anger, or by sensations like pleasure or pain. For this reason, virtues like courage, endurance, self-control, and temperance can come to the assistance of wisdom.

Wisdom and mistakes

It is a popular belief that we gain wisdom (or gain it most effectively) by learning from our own mistakes.

“Wisdom is a virtue of old age, and it seems to come only to those who, when young, were neither wise nor prudent.” ―Hannah Arendt

On the other hand, learning from other people’s mistakes may be the more prudent way to go about it (#LFMF!). LessWrong is in part a collection of dead-ends marked by warning signs, pointing out the mistakes in reasoning that others have been waylayed by.

But you typically learn other people’s mistakes from other people’s failures, which may leave your own artisanal mistakes unchallenged. If you are willing to strap on your theories and go into battle with reality until you lose, you will be more likely to discover and shed your worst theories. This takes courage, confidence, industriousness, and a willingness to fail and to admit failure.

Surfing less unwisely

“The fool doth think he is wise, but the wise man knows himself to be a fool.” ―Shakespeare (As You Like It)

At least since Socrates, wisdom has been associated with epistemic humility. The “LessWrong” name itself nods at that tradition: To be more wise, assume that you are wrong, try to figure out where and how, patch that up as best you can, lather, rinse, repeat. Don’t be too proud of the nuggets of wisdom you have dug up, but occasionally peer into the vast voids of ignorance, the blank spaces on the map. Imagine those things that could be true that would mean utterly overthrowing most of what you currently suspect to be true. Don’t become attached to your best guesses or too inclined to round off a high probability into a certitude, but always prefer reality to your favorite hypothesis.

Wisdom seems to have less to do with arriving on the firm ground of confident understanding, and more to do with learning to surf the unstable edge of profound uncertainty: neither clinging to the barely-buoyant flotsam of belief nor being pulled out into a sea of nihilism by a undertow of skepticism.

Mystical vs. rational wisdom techniques

To understand and make our way in the world around us, we try to systematize, to find regularities, to discover cause-and-effect relationships, and so forth. We create a map, using our knowledge of the territory that we have passed through, to help us predict the territory we are about to enter. By extrapolating from suggestive patterns in the world, our maps can illuminate things we do not experience directly, and can suggest places to look to discover more than we might have stumbled upon on our own. Habits of rational thinking help us to keep our maps from misrepresenting the territory, and warn us about where our maps might be misleading even when they are as accurate as we can make them.

Mystical wisdom techniques suggest a different way to go about it: rather than just improving your map and your map-reading, take some time also to look directly at the territory and improve the quality of your vision. The advantage of this approach is that you lose the compression artifacts and other errors that come from trying to reconstruct the territory from the map. A disadvantage is that while maps can sometimes be shared, visions have to be turned into maps before they can be — and by the time you have turned your vision into a map, there may be little to recommend it when compared with maps arrived at through more rational methods.

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