Philosophy is the love of wisdom. But throughout its history, philosophy has also been haunted by wisdom's opposite: foolishness. So what is the relationship between philosophy and foolishness?
If philosophy has always been preoccupied with wisdom, its relationship with the opposite of wisdom—foolishness—has always been a vexed one. One reason for this is that throughout the history of philosophy, the relationship between wisdom and foolishness has not been one of simple opposition. Instead, it seems that for some philosophers, at least, there is a kind of wisdom in foolishness.
We already know that Socrates was a self-confessed know-nothing. And also we know that for the Zhuangzi there is something wise in giving up in the pursuit of wisdom. So when thinking through what it means to be wise, we are going to have to ask what it means to be foolish.
Looking for the light: The wise fool and the lamp
The idea of the Wise Fool has a long history. This history goes back at least as far as Socrates. Arguably, Socrates was both a fool (he was ignorant) and wise (he knew he was ignorant). Being both wise and a fool, he was able to fool with those who claimed wisdom for themselves, and in fooling with them, he could demonstrate that they too were fools — only more foolish fools than he was himself.
The Wise Fool is someone who, in their search for wisdom, appears foolish in the eyes of the world. In the ancient Greek world, the philosopher Diogenes the Cynic was even more well-known than Socrates for his foolish wisdom. In one famous story about Diogenes,
Plato defined Man as a featherless biped. The definition was generally well received. But Diogenes refuted it by plucking a chicken, bringing it to Plato’s Academy, plopping it down and proclaiming, ‘There’s Plato’s Man for you!’ 
Plato was, unsurprisingly, not impressed by Diogenes. He allegedly described him as 'Socrates with a screw loose.'  And Diogenes's behaviour was admittedly bizarre. Another much-retold anecdote is that he went around in full daylight holding up a lamp. When people asked him what he was doing, he said, 'I'm searching for an honest man.'