It is said that, back in ancient Greece, people from all city-states looked up to the Oracle at Delphi as one of the most important religious sites in the entire country. Ancient Greeks put so much stock in it that the fate of kingdoms often rested on the prophecies uttered by the Oracle. So, when the Oracle declared Socrates to be the wisest of men, it was a big deal. Socrates, though, didn’t buy it. He protested that he didn’t know much, and that Greece was full of people much more confident in their knowledge than he was in his. To prove the Oracle wrong, Socrates began talking with all the intellectual stars of his day. It quickly became apparent that these people sounded very self-assured and boasted loudly about their wisdom, but their self-assurance was mere posturing and their boasting was made of empty words. The more Socrates investigated, the more obvious it was that their wisdom stood on shaky legs, and that their theories didn’t hold up to scrutiny.
This was exactly what the Delphic Oracle had been trying to say. Socrates was wiser than all of them paradoxically because he didn’t consider himself wise and was painfully aware of the limits of his knowledge. Lacking the arrogance of those who believe they know everything there’s to know, Socrates had to remain constantly open-minded, ready to experiment with many different paths, and willing to question everything—including his own conclusions. And this was precisely what made him wise.
Across the world, in China, Taoists had reached the exact same conclusion. In the Tao Te Ching we find the line “Who knows that he does not know is the highest.” And similarly, Chuang Tzu, one of the other leading Taoist philosophers, declared, “The torch of chaos and doubt—this is what the sage steers by.” What the Delphic Oracle and the Taoists were suggesting is an approach to knowledge that Alan Watts has described as “the wisdom of insecurity.”
On the surface, all of this sounds odd. Why is insecurity a good thing? Why chaos and doubt? Why praise those who acknowledge their ignorance? After all, insecurity and doubt can be paralyzing forces. They can make us too timid and insecure to commit to needed action. This is what Bertrand Russell was thinking of when he wrote, “The problem with the world is that the intelligent people are full of doubts and the stupid ones are full of confidence.” This line, in turn, was inspired by WB Yeats’ sentence, “The best lack all conviction, while the worst are full of passionate intensity.”
Clearly, this is not what we are talking about. No wishy-washy crap that only leads to weakness and indecision. What we are advocating, instead, is the perfect antidote against dogma, which is the place where all good thoughts go to die. Worshiping mistaken ‘knowledge’ or, more optimistically, partially true knowledge makes us miss our blind spots. We take a concept too far, where it stops being a healthy idea. We don’t counterbalance an insight by taking into account a good objection. And before we know it, we end up spouting ideological articles of faith that have lost whatever good inspiration they may have started with. The wisdom of insecurity, on the other hand, invites to constantly test our most cherished conclusions. Doubt, according to the Taoists and the Delphic Oracle, is the root of all curiosity, all inquiry; and this is why it is a precious source of wisdom. Dogma works against this. Dogma fears that if it doesn’t make bold assertions of having a monopoly over the truth, it will appear weak and indecisive. So, in order to cultivate the appearance of strength, dogma shuns the reality of strength.
All of this came to mind recently when a friend sent me a whole bunch of YouTube videos debating a particular topic and asked for my thoughts. Halfway through formulating my response, I realized that what I was writing was utter and complete bullshit. It was fairly well thought, but the problem was my knowledge of the topic at hand was superficial at best. My grasp on the evidence was between amateurish and non-existent. And of course, without a good grasp on the evidence, I can’t really have an educated opinion.
Over the past few years, social media and the democratization of knowledge have given a chance to everyone to publicly express their opinion on any possible topic. I am not one to worship the experts of any one field since, often, they act as gatekeepers and are resistant to embracing new perspectives. I have seen too much proof of the contribution brought by non-experts to dismiss them. But at the same time, opinions, if uneducated, are of limited value. Not all points of view are born equal. Some are based on deep research and solid understanding of the evidence. Others are based on meandering in the dark corners of the internet for a few minutes looking for something to confirm our prejudices. Choosing to remain open to alternatives and resisting the urge to express strong takes on every possible topic, including those we barely understand, may not be such a bad idea. In an age when it feels like a crime not to have strong opinions on everything, sometimes saying ‘I don’t know’ may be the healthiest response. The Delphic Oracle would approve.
Well, darn. This is an excellent essay. I read it at 9h30, 26 May, 2025, Paris time. Not that anyone appointed me Critic of Daniele Bolelli, but I got a lot more out of this than my attempt to listen to The Drunken Taoist. But maybe I should do a deep dive into the origins of this Substack and the podcast in question so I have a valid opinion. This much uncertainty makes me some kind of genius, I guess. That's real scary. For me and everyone else.
This is an excellent essay and for me, very timely too. It helps me understand why the Socratic method of teaching is so effective and it reinforces the reason that Jesus taught in parable: both methods require the listener to engage. And if they choose not to, they can walk away unoffended to be invited another day.