I’m spending this week in school. Surrounded by teenagers, I am transported back to my own school days, back to a time when cool was the rule. I came into high school decidedly uncool, with my charcoal smear mustache, fresh off the boat from three years in a small Israel town. I knew nothing about pop culture, sports, music, how to dress or swear. My mother still cut my hair.

By the time I graduated, I was cool—ish. By day I was a good student. I starred in the school play, I edited the paper, I illustrated the yearbook. At night, my friends and I were automatically waved past the velvet rope at Studio 54. We were regulars at CB’s, Mudd Club, Area, Heat, Danceteria, and the Roxy. We hung out with junkies in Alphabet City and smoked dope in the theatre balconies of Time Square. We went to outlaw parties on the High Line, thirty years before it became a tourist attraction, climbing the rusty pylons to drink from brown bags on the crumbled tracks. New York in the ’70’s, it turned out, was cool as hell and some of it rubbed off on me.

When I graduated from college and came back to New York to enter the work world, I was the new kid all over again. I soon discovered there was hierarchy of cool among ad agencies. Ally, Scalli, Della Femina, Lord Geller and Ammirati ruled the early ’80’s only to be eclipsed by newcomers like Riney, Hill Holiday, Kirshenbaum, Deutsch, and the coolest of the cool, Chiat Day and Weiden & Kennedy.

I just assumed I wasn’t cool enough for any of these top shops and worked for the intellectual agency instead, Ogilvy & Mather. Still, I always looked with dorkish yearning at the cool guys. It seems that to work on Apple or Nike required some chromosome I was missing. I didn’t call people ‘bruh’, didn’t have any tattoos or a soul patch or a pony tail, hadn’t backpacked through Morocco or Burma, didn’t own a black lab with a bandana or a Harley. Some magic was working these super-cool places, magic I wasn’t privy too.

Recently I met a bunch of people who worked at Weiden in that period, thanks to my girlfriend, Jenny — who’s one of them. Nice guys, smart enough, but not another species. They may have felt little more empowered to take risks, more likely to see off-center ideas, more free in some ways, but they put their black Levi’s on one leg at a time, same as me.

I’ve had the same experience with artists I admire. People who I thought had drunk some magic elixir, or carved their own pens out of logs of Brazilian Zebra wood which they’d felled themselves, people who seemed to be gods but were just marginally cooler and freer and looser and are confident than I was. With a little effort, a little willpower, I could see that I could be as cool as Robert Crumb or James Jean or Lapin or Tommy Kane.

I look at the high schools kids I worked with this morning. The coolest ones aren’t the ones with silly haircuts or eyeliner or extreme clothing or the outline of cigarette packs in their pockets. They’re the one who are open, confident, curious … themselves. Assuming you are style handicapped, ungifted, uncoordinated, hopeless, backward, well, that’s just your monkey being uncool.

Grace and aplomb can be yours. Just take a deep breath and walk into the room like everyone’s your pal. Draw that same way. With clear eyes and an open mind. With confident strokes, no matter how wonky. With a willingness to fail and an eagerness to learn. Laugh at yourself, take a chance, keep coming back, and, lo and behold, you’ll be super-cool.