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School for Cool (Speech)

by Jay Connolly 11 months ago in how to

Three paths up the high school social ladder

School for Cool (Speech)

I was clearing a paper jam from the photocopier near my classroom the other day when I heard a girl ask her friend, “Why are we even here?” 

I thought that was an important question—and I knew at least one answer—but the people left before I finished with the machine. 

I don’t know if the person meant it as a big question—like, “Why do we exist in the universe?”—or a small one—like, “Why do we labour under the dictatorship of school instead of beginning the Revolution?” 

It doesn’t matter. The answer to both questions is the same. 

In North America, during years spent at one high school or another, teenagers grapple with the question of cool. Are you cool? How cool are you? Or are you uncool? And if you’re uncool, just how uncool are you? 

Some of you have been forced to confront the dark knowledge that you’re not cool and possibly never will be high school cool. For reasons I’ll explain later, you may be the most fortunate people in the room. 

Before even I was born, cool was called hip, boss, groovy, or right on. Tubular and rad and wicked came later. Last week, my grade 11s told me that today’s A-list words include dope, tight, sweet, sick, awesome, fly, swag, and fire. 

But they all refer to the gold standard of in, which is cool. 

You’re here to figure out your cool.


When I was 9 or 10, people started wearing designer jeans. It was okay to hit school in department store clothes, but it was cooler to own something different, something rare and more expensive.

One day when my mother dragged me out shopping, I saw in the window of a store a pair of patchwork, bell-bottom jeans. Flared pants were it. If you walked quickly, the pant legs would snap against each other like flags in the wind. 

My whole life I’ve been subject to sudden convictions, in the depths of my materialistic heart, that objects can change me. I convinced myself that those jeans would make me cool.

My mother was not convinced. I was a chunky kid, and I sometimes had to choose my clothes from the . . . well, from the “husky” section at Sears. Very un-cool. The jeans did not fit me well. I looked like James Cordon in a leotard—but I thought if I went to school in those pants, I could just lean against the fence like a chubby little messiah and wait for my people to gather round me.

My mom told me, “They’ll shrink when I wash them.”

“I’ll lose weight,” I said. 

“Well, then we’ll come back when you do.”

My mother did not understand that she was ripping from my life the opportunity to fit in effortlessly. Many of you will appreciate that it mostly doesn’t work that way—that the pants would not have made me cool. They would have made me look like a try-hard.

But in my mind they were going to change everything.

Attachment cool—the cool of fashion and things and surfaces—remains the most conspicuous kind of cool. 

Attachment cool is about the stuff you own—rare things, different things, weird things, trendy things, expensive things. Attachment cool is about decorating yourself so that maybe no one will see you. 

Attachment cool means wearing the right clothes, or surrounding yourself with the right people. You get it with tattoos and vintage Ray-Bans and the latest hair style. It’s cool you can buy. Advertisers spend billions of dollars to invest their products with cool. At its worst, attachment cool is nothing more than taking instructions from massive companies. 

A couple years ago, following the September release of a new iPhone, I heard two of my students plotting to get the new device. 

“What difference does it make?” I asked them. “What’s it gonna change?”

One of them said, “Don’t you want to have what no one else has?” 

“Absolutely,” I told him. But in my mind, I was thinking this: the ultimate cool doesn’t come from owning things anyone can own. It comes from being something no one else can be.

In the age of fast fashion and 6-month marketing cycles, companies release new products just as the last one’s losing its glitter, but there’s a point where market saturation kills cool. I get the sense, for example, that tattoos are not quite as important in your minds as they were to students five or seven years ago. That may be partly because many of your parents have them. When your mom has sleeves and your dad wears a throat tat, it’s not quite as rebel to get inked.

Of course, the dark danger of attachment cool is the risk that you’re nothing more than the stuff. Attachment cool can turn you into a little robot who simply runs the current cultural code. It can bury your individuality under so many layers of objects and styles that you become nothing more than an expression of the latest trends. 


The second kind of cool is de-tachment cool. If attachment cool is about showing off, then detachment cool is about not showing off.

Last year, I asked the kids in a grade 12 English class if they were cool. Only one hand went up—and that person was joking. My students understood the first rule of image management—that if you think you’re cool, or need to be cool, then you’re not. If you confess to being cool, then that means you’ve been thinking about your own cool—and it’s uncool to worry about cool. 

De-tachment cool is the cool that comes from not caring. 

It’s right in the literal sense of the word itself—to be cool to something is to be without the heat-energy of passion or concern. Detachment cool people are rarely impressed. For example, if you tell a cool person, “Nice tattoo,” or say, “That’s fire, man,” they might look surprised. Like they’re not sure what you’re talking about. And if you say, “The tattoo — on your face!”—they might go, “Oh, yeah, right, yeah . . . I guess.”

When I was 18, I had a job as delivery driver. I loaded the company truck every morning, and then I rolled through the Okanagan Valley in the sunshine with no one to answer to for the rest of the day. Driving was fun, and the truck had an powerful stereo system. 

This was in the days before everyone dove under headphones. Our music was a proclamation of identity—nowhere moreso than in a vehicle. I remember spinning the volume up to 11 and attacking the traffic with my favourite songs. This was music made physical—the kind of volume that buzzed in the metal and glass of the truck and shuddered through your body if you were nearby. 

I remember rolling down the windows and pounding the streets with Kiss and Aerosmith and Nazareth and AC/DC. On the highway, I’d keep things at a reasonable level, but in town, where people would see and hear me, I ran the volume just beneath the level of instant hearing loss. And when people stared at me, I’d look at them like, “What?”

You have to find the balance, of course. If you’re too obvious in your construction of cool, you’ll wreck it. I’ve seen students fall so deeply under the spell of new sunglasses that they over-wear them, keeping them on in dim buildings and on dark days. I once saw a kid here wear his sunglasses in the rain, and I thought, “Dude, no!”—because as soon as someone said, “He thinks he’s so cool,” it would be over. 

Yesterday in grade 12 English, a student looked at me and said, “You have all the latest Apple gadgets.” And I said the only thing I could say, under the circumstances, which was, “Oh, wha? Oh . . . I guess.”

Detachment cool means not noticing your cool stuff, not seeing your own cool behaviors, not worrying about danger, and not engaging with rules. If you want to be detachment cool, then stay out of the way. Avoid expectations. Hang back. Do not commit.

Unfortunately, detachment cool turns some people into cynical side-line critics—the kind of people who mock the effort, ability, and achievement of others. 

I should make clear that cynicism and skepticism are important human resources. They protect us from quacks, cheats, swindlers, and fakes, but they also take time to grow into. 

I was a cynical teenager, but eventually I realized that the cool of detachment is sometimes the cool of anxiety. Show me a person who’s quick to condemn others for their skills and involvements, and I’ll show you person who’s probably worried that they’ll never find their own way to shine. 


Which brings me to a third kind of cool. It’s something the attachment people can’t buy. It’s the thing the detachment people fear. I don’t have a name for it, but it’s the kind of cool that fills me with respect, and I always react to it the same way. It makes me shake my head in stunned admiration. It makes me mutter to myself, “Cool”—because that’s what I say when I catch people rising above.

I’m talking about the cool of total commitment. The cool of effort unrestrained by the fear of failure or the awareness of audience. The cool that comes from being so into building skill or ability or knowledge that you don’t care about the opinions of others. It’s the cool of unembarrassed enthusiasm. It’s the cool of setting your inner compass according to your values and your dreams instead of letting other people point you in a direction that makes them feel comfortable.

It’s easy to be detachment cool because all you have to do is withdraw and criticize. The cool I’m talking about is difficult because the path to excellence usually involves some failure, disappointment, and recalibration. But the rewards are huge. In detachment cool, you tear people down from the outside. In this last kind of cool, you build yourself up from the inside. 

The American poet Robert Pinsky wrote that “one of the strongest human cravings is for difficulty.” If you want to know who you are, then tackle a challenge that matters to you. The process will teach you about the pressure points in your own personality—about what frustrates you and makes you want to quit, and about the small breakthroughs that inspire you. You will endure the tension between your patience and your impatience. You will come to appreciate the rewards of slow progress. Your attachment cool friends won’t understand . . . your detachment friends will tell you to give it up . . . but your true friends will shake their heads in respect and wonder. 

Some of you may be thinking, “Yeah, sure, but I don’t know what I care about.” Fair enough. In that case, you have to care about it all, because only by giving your full effort to everything you do will you stumble over the pursuits worth placing at the center of your life.

A former student of mine named Brendan Tang discovered pottery in high school. He was a superior math student, and he considered medicine as a career because his dad was a surgeon, but he loved pottery, so he gave himself permission to pursue it. He has shown his work around the world; one piece sits in Canada House in London, England, and many others are owned by first-rank collectors. Brendan is a celebrity in a world that matters to him. 

I could tell you a hundred other stories about students who found their passion in law or medicine, in business or engineering or geology, in the visual arts or the performing arts. Last year, I ran into a former writing student named Katherine. She had wanted to be a veterinarian. She now works training animals for movies, and she loves the challenge. 

In the past, I’ve heard people reject significant effort by saying things like, “What’s it going to get me?” Here’s a better question: “What’s it gonna make you?” And I know the answer: It will make you the kind of person accustomed to reaching deep into the resources of your own self and spirit to produce effort and determination and commitment. It won’t guarantee success, but it will train you to become the kind of person who’s ready to put themselves on the line. It will make you a person of character. It will teach others that they can count on you. It will remind you that you can count on yourself.  

Everyone in this room has at least three unique assets—the genetic code you were born with, the set of experiences and environments you’ve been exposed to, and the original self forged from combining those two factors. Attachment cool wants you to reject your inner resources in favour of things; detachment cool wants you to call down others instead of becoming a champion in your chosen field of challenge. I’m telling you there’s no cool as powerful as the courage to find your own way.

I said at the beginning of these remarks that the terminally uncool may be the luckiest people in the room. It’s because they often reach a point where they simply give up on cool. They decide to like who they like . . . to do what they enjoy . . . to work at what gives them satisfaction . . . and to be who they are. And if they keep doing that, then almost inevitably, they will become the kinds of people who make me—and probably many of you—shake my head and say, “Cool.”

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Jay Connolly
Jay Connolly
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Jay Connolly

Jay Connolly teaches English at a Canadian boarding school.

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