I think it’s related, but not in the way you’re implying: He seems to view it as a personal failing that he didnt ignore the awkwardness to “solve the problem”

I think it’s related, but not in the way you’re implying: He seems to view it as a personal failing that he didnt ignore the awkwardness to “solve the problem” of no one memorializing his friend and thinks about that inability to perform in the moment often, because he wants to be someone who can “rise to the occasion” in such moments. You seem to have a different problem, eg a bad work-life balance or lack of meaningful duties to perform.