Hi Jason,

I just turned 30. How do I keep on staying cool without looking like an old guy who’s trying to stay cool?

Indy, IN+

You might want to know this much about me: I’m a 35-year-old who, the last time he made a conscious effort to be cool, ended up buying a pair of black slacks at H&M that were just perfect for a wild-and-crazy night of catering. And it has always been thus with me. On the other hand, I’ve never been a mustachioed hipster wearing a T-shirt with the Yoo-hoo logo on it for some reason, so I’m fortunate for that.

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. I’m not suggesting you undergo some sort of instantaneous transformation into “maturity” involving a fanny pack and a Land’s End catalog—30 is still quite young, you know—but I think you need to at least begin shedding the skin of your 20s. Hang on at your peril. There’s a 40-year-old out there who still wears shirts that allow him to show off his barbed-wire-armband ink. Don’t become him.

But you could, you know, just be a guy who knows a lot about a lot, who’s got some awesome stories because he’s lived almost a decade beyond the campus quad, and who’s shown some follow-through on the ambitions he spent so many years blabbing about in his 20s. You also could be in better shape than all the guys who bloated up in college, too. Not so “cool,” but cool and durably so.

Look, no matter how I play with quotation marks, I suppose there’s a part of me that still wants the girl in the fishbowl sunglasses and Ramones T-shirt she got from an eBay vendor to invite me to a roof-deck party where a DJ is remixing music that I never heard originally, if for no other reason than it would somehow signify that the faint bags I’m beginning to notice under my eyes even after a good night’s sleep are imaginary. But they aren’t.