Over time, I've begun to abandon an overt search for "depth," even if thinking well and clearly and deeply, whatever that means, remains the goal. It's clear to me now in the fullness of overweight middle-age that the search for depth and "deep conversations" was a form of youthful vanity. The unspoken self-flattery, of course, that I was capable of such depths, that we could come together and improve our thinking and that we would congratulate ourselves and each other about how well and how deeply we could now think, now that we were very 21 and so wonderfully mature.
Amidst the wreckage of my life, youthful aspirations long since cast aside once seen as lies I told myself and/or lies I was told by others, I am more inclined to seek out shallow conversations. I still wish to reason well and think clearly but the tone I seek is much more the genuine humility of "isn't wonderful that we can come together and reason and isn't it a tragedy that we do so so poorly, even after all these years?" Which is to say, at some point in your life-long learning, both the vastness of the universe and the hard limits of excitable, hierarchical primates should make SOME impact on your consciousness, hopefully provoking some moderate sense modesty and humility about the quality of your thinking and the idea that perhaps learning to think well is a life-long journey of trial and error in thought and deed that will at some point be rudely interrupted by death, well before you have finished learning what you want to learn.
Which isn't to say that humility can't be it's own kind of prideful trap, of course. "Isn't it wonderful how humble we are now?" is itself not a terribly humble thought. The question is, am I seeking a self-flattering identity or knowledge? Do I desire to be seen as "deep," and lauded accordingly, or am I still searching for answers to questions I still have a hard time even finding the words for? I'm much more interested in the latter than the former as time goes on, my inner Smart Kid howling in chains notwithstanding.
