Yeah, he battled depression and was on meds. He tried to get off of them due to the terrible side effects, and ended his life shortly afterwards. As someone who has been on and off meds for anxiety and depression, I don’t blame him for being sick and tired of them.

I remember reading that he was especially interested in Ludwig Wittgenstein, which would explain his flirtations with fatalist and solipsist thought. I think you’re spot on with the observation that he was unsure of himself. I think that reflected heavy in his writing, and why even in that famous Kenyon College address, he dispensed out moral wisdom in terms of being more emphatic and caring, and then later on in the same address tells students to not take everything he’s saying as gospel. I don’t think it was some brand of cowardice. I just think it’s part and parcel of being in a society that grounds down individuals, exacerbates or even creates their mental battles, and historically unmoors them at birth. Plenty of leftists have fallen into those same depths of despair and mental anguish