If by "cool" you're referring to some sort of constellation of wardrobe, body modification, and iTunes library that approximates what someone eight years younger than you has, you don't stay cool. I mean, you can sort of pantomime it for a while, and since you've just turned 30 it wouldn't be so difficult for you. But this kind of cool shifts quickly, and assuming you're a typical 30-year-old who now has obligations beyond smuggling peyote into your dorm room, it's going to move faster than you. Maybe not much faster, at first, but coolness requires precision—either you're on top of it or you aren't. And at this point you probably have little time to figure out what the official position on the Yeah Yeah Yeahs sucking is. If you do have the time, you probably won't for much longer.
Some people manage to replace cool with the confidence that comes from experience and accomplishment, and, increasingly, the people in your life will start to value those things more as they themselves move on from their 20s. Coolness was a placeholder, something they leaned on as they assembled themselves.
Twice in the last month or so, I've had people ask me what new music I'm listening to. Both times, the honest answer has been "I don't listen to new music, I listen to old music." In high school, I was on the bleeding edge, but somewhere towards the end of college/beginning of grad school, other things became worth the time I used to devote to following new bands. I know what I like, and the kinds of things I like, and that's fine by me--it doesn't exclude the occasional worthy new thing, but the days of chasing novelty for its own sake are behind me. Thankfully.
I think there's a pedagogical equivalent to this, which is the desire for novelty less because a new source can add something to what you're teaching, and more because you're bored of reading the same things over and over again (this is not a criticism, since Lord knows one day I will feel exactly the same thing, but I worry that this valorizes the experience of the teacher, who has read, say, the Republic dozens of times, over that of the student, who may never have encountered it before); this is probably the honest explanation for the funky-looking course syllabi NR-type conservatives mock (if you read and re-read the great works, you'll start looking for perspectives that keep them interesting, and that'll lead you down some bizarre roads).
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