One common excess marks the character of most good philosophical friends and conversation partners. That excess is arrogance.
The path of philosophical life is not desired by the ignoramus. And it cannot be disclosed to the self-loathing man. Nor to the complacent man. Only the arrogant man (1) relishes what is higher, (2) wants it for himself, and (3) believes himself to be worthy of possessing it.
Hence, the path of philosophical life is desired by the arrogant man for he believes it to be the best form of life and he wants it for himself. And yet, such a path cannot be disclosed to him until he is humbled. Humbling occurs not least when he recognizes that he has been a fool. For many years, a fool. Many years spent in vain. Philosophy brings him to confront his foolishness and to feel shame for having lived this way.
This turning is the beginning. Desiring would not have been possible (or, in any case, likely) without the one so desiring having been arrogant in the three respects above. But the path remains hidden so long as he remains so. Herein lies the perplexity, the paradox.
To set foot on this path is to have one’s arrogance humbled. Philosophy humbles time and again with gentle admonition. Only then is the shining path revealed to the aspirant and this for the first time. Now it is that the aspirant no longer wants to possess wisdom nor does he believe himself worthy of having it. (Wisdom cannot be possessed.) However, his estimation of its height has only increased exponentially, and he is stirred and stirred by the mere intimations of its resplendent beauty. And all this, as Benedict says of humility, is only the beginning…