Knowledge is not wisdom. And wisdom does not arise from being spoon fed facts. It comes only from experience. Teachers force-feed math, science, language, geography, and other bodies of obligatory content. But no amount of facts can replace experience, especially the wonderful privilege of failure. The skinned knee teaches more than the safety manual. The rejected manuscript teaches more than the writing guide. The broken heart stings more than any poem. People talk about AI as if it can reach the source code of wisdom. But it can't, because it's not alive. It doesn't suffer disappointment. Heartache. Longing. Ridicule. It can mimic the words of those who have, but it misses the mark of the experience. It's a robot cheating off the paper of the scared boy sitting next to him, copying the answers without ever having wrestled with the questions. John Dewey wrote that “there are but two philosophies. One of them accepts life and experience in all its uncertainty, mystery, doubt, and half knowledge and turns that experience upon itself to deepen and intensify its own qualities—to imagination and art. This is the philosophy of Shakespeare and Keats.” The second is the quest for certainty. AI eagerly takes up its mantle. This philosophy treats ambiguity as defect, mystery as inefficiency, doubt as error to be corrected. It seeks fixed, absolute knowledge and pursues certainty through abstraction, system-building, and fixed outcomes. It wants the answer key to existence. But that's not life. That’s Macbeth's despair. It’s life as “a walking shadow, a poor player that struts and frets his hour upon the stage and then is heard no more... a tale told by an idiot, full of sound and fury, signifying nothing.” The quest for certainty, carried to its end, arrives at nihilism. If meaning must be “proven,” then nothing means anything. There’s a reason Shakespeare never resolves Hamlet's questions. Keats doesn't explain the Grecian urn. He called this comfort with ambiguity negative capability; the capacity to remain “in uncertainties, mysteries, doubts, without any irritable reaching after fact and reason.” Tarantino never reveals what's inside the briefcase. Because that's not how life works. The mystery IS the meaning. The human experience is not about gathering all the data, plugging it into an algorithm, and being handed an answer. It's about embracing uncertainty. It’s living inside the question. A machine that mimics human expression is not human precisely because it is programmed, compelled to generate a response. It cannot sit with silence. It cannot shrug. It doesn't realize that sometimes there is no answer. Or that the absence of an answer is itself the point. Only humans can appreciate that. Only the living can find wisdom in not knowing.