I remember wishing he’d used some term other than “a critic” — a term too easily mistaken for a profession, a position — when what he really means is a critical person: the Merriam-Webster 2. definition of critic (“one given to harsh or captious judgment”), rather than either the 1a. (“one who expresses a reasoned opinion” on matters of “value, truth, righteousness, beauty, or technique”) or 1b. (“one who engages often professionally in the analysis, evaluation, or appreciation” of art). If he meant that last one, all he’d be saying is that he made a spectacularly shitty critic, which is not his point — although he does seem happy to let the lines blur between these things, to let it be inferred that critics are merely critical, just like it says on the label; this is what’s known in the world of not-saying-YES as a “dick move.”
Really what he’s telling in this paragraph is the story of an age cohort, or at least a certain segment of one.
[M]eanwhile along come a whole bunch of younger people for whom these issues are not all that vexed or pressing, people who are fluent in irony and sincerity both and don’t need to be told how to love earnestly, people for whom “say YES” is not a profound and meaningful shift in mentalities but just a stitched-sampler reminder of something very, very basic, and maybe in this sense every generation digs a hole and then goes around preaching about the importance of climbing out of it while young people nod politely at them and dig different holes entirely.