People need to be able to express interest in one-another somehow, and asking people about their hobbies is way better to me than asking about people’s jobs. Asking people about their interests is pretty harmless, compared to asking about jobs in a world where a lot of people hate their jobs, and rampant classism means that the question is sometimes a way of sizing people up. Besides, for a lot of people the only thing their job says about them is “this is the shit I came across that pays my bills for now.”
The bit about “wokeness” and “cancel culture” is a bit surprising to me, since I always figured his politics were closer to generic liberalism.