This is one of my favorite passages from Truth and Method. It is very much on the topic we are discussing.
Thus the historical nature of man essentially implies a fundamental negativity that emerges in the relation between experience and insight. Insight is more than the knowledge of this or that situation. It always involves an escape from something that had deceived us and held us captive. Thus insight always involves an element of self-knowledge and constitutes a necessary side of what we called experience in the proper sense. Insight is something we come to. It too is ultimately part of the vocation of man—i.e., to be discerning and insightful.
…
If we want to quote another witness for this third element in the nature of experience, the best is Aeschylus. He found the formula—or, rather, recognized its metaphysical significance as expressing the inner historicality of experience—of “learning though suffering” (pathei mathos). This phrase does not mean only that we become wise through suffering and that our knowledge of things must first be corrected through deception and undeception.
…
Understood in this way, the formula is probably as old as human experience itself. But Aeschylus means more than this. He refers to the reason why this is so. What a man has to learn through suffering is not this or that particular thing, but insight into the limitations of humanity, into the absoluteness of the barrier that separates man from the divine. It is ultimately a religious insight — the kind of insight that gave birth to Greek tragedy. Thus experience is experience of human finitude.
…
The truly experienced person is one who has taken this to heart, who knows that he is master neither of time nor the future. The experienced man knows that all foresight is limited and all plans uncertain. In him is realized the truth value of experience. If it is characteristic of every phase of the process of experience that the experienced person acquires a new openness to new experiences, this is certainly true of the idea of being perfectly experienced. It does not mean that experience has ceased and a higher form of knowledge is reached (Hegel), but that for the first time experience fully and truly is. In it all dogmatism, which proceeds from the soaring desires of the human heart, reaches an absolute barrier. Experience teaches us to acknowledge the real. The genuine result of experience, then—as of all desire to know—is to know what is. But “what is,” here, is not this or that thing, but “what cannot be destroyed” (Ranke).
…
Real experience is that whereby man becomes aware of his finiteness. In it are discovered the limits of the power and the self-knowledge of his planning reason. The idea that everything can be reversed, that there is always time for everything and that everything somehow returns, proves to be an illusion. Rather, the person who is situated and acts in history continually experiences the fact that nothing returns.