How to be Cool

And Why Writing This Means I’m Not

I was once at a party when a friend asked a small group of us what word we would want others to describe us as. We were more or less in a circle, and like good order-loving Canadians, took turns answering. “Kind” the first person said. “Compassionate”, said the next. “Generous” is another one I remember.

By the time it was my turn, the number of veiled, nauseatingly self-serving responses was enough to make even the Dalai Llama go “oh come off it, people.”

The word I chose was “cool”. Yes, “cool”, that’s right.

It is difficult to describe what cool actually is. The word can mean everything and nothing at the same time. Ask ten people to define cool and each will produce their own take on it, and in most that take will be a reflection of their own desires, misgivings, and choices. In that way, it is a lot like the word god.

The foregoing is meant to explain how (un)surprising what happened next was. I got verbally undressed in a way that only a word so offensively relative can inspire. Using the other “c” word would have left me less judged.

“You know how uncool it is to say that?” said the first person — Duh. If I was cool, I wouldn’t want to be cool. Old men desire youth, but drowning men are not thirsty.

“I can’t believe that is your choice.” — Yah me neither. I guess I surprised us both.

“Why do you care what other people think?” This one bothered me the most. The entire premise of the question involved the tacit desire for the approval of others. It’s like asking a fuck-marry-kill hypothetical and then accusing the responder of being homicidal.

“Fuck you, you douche”.— ☹

Okay that last one didn’t happen. But you get how the rest of the conversation went. Turns out the desire to be cool, however ambiguous that word may be, makes you an uncool asshole.

All this aside, my answer sparked a conversation. What is it to be cool?

What is it to be cool?

Some, dare I say lazy, people believe cool is just, like ya know, cool? To these people, you can’t define or categorize cool. Cool is like the quantum observation paradox. The moment you see it, it no longer exists. If you don’t know what I’m talking about, you’re probably cooler than I am.

Soft-spoken cool

To others, cool is about soft-spoken confidence. Zen master cool. Walk into a room and say nothing cool. Clint Eastwood in Gran Torino cool. Bo Jackson cool. B0, perhaps the greatest athlete to ever live, wasn’t much for showboating or self accolades. He didn’t love the the media or press conferences. This may have been an aftereffect of his childhood stutter, but even so, his genuine and visible discomfort with that kind of fame made him bigger than his coolness.

“Hard”-spoken cool

Then there’s the opposite. The “hard”-spoken cool you could call it, with its loud, confident, mania-fueled exuberance, and unapologetic flash and self-endorsement. Unlike its soft-spoken counterpart, this variety tends to reap the benefits of what social status can buy.

The Tao Te Ching advises us that those who know do not say and those who say do not know. Lao-Tzu left out the part about how those who say get laid a lot more.

if [A->B] & [B->C] then [A->C]

Then to some being cool isn’t so much just about you at all. It’s not about your clothes, your car, or your house. Goods can be bought, after all. Instead cool is about those around you. What celebrities you know, what clubs you can get into, and how good your drug dealer is. Evidently there is a transitive property of cool. If Vince is cool and Chad knows Vince, then Chad is cool. Vince is probably also a douche. Quod erat demonstrandum.

Counter culture

I used to live in Seattle, where another type of cool was, and I say this with no evidence, pioneered: counterculture cool. It took some of its cues from Nirvana but existed long before. It’s a type of cool iconified by hipsters and grunge and any other group fighting against the mainstream and “cool” itself. “I’d rather be dead than cool” said Kurt Cobain — channeling directly his disdain for conformity and popular culture. And we all know how that ended.

There is so much irony in a statement like that. Only someone who cares enough about being cool would rather die than be it. Moreover, counterculture itself has become the mainstream. Marketing departments caught onto this long ago and their rebellion-endorsing campaigns have matured to the point where even something as banal as toothpaste can sell for being “different”.

Counter counter culture

One of the reactions to the counter-culture paradox is the emergence of norm core. If you don’t know what norm core is (and I hadn’t for the longest time) it’s a style characterized by dressing up like your mom and dad. Think unremarkably cut jeans with new balance sneakers. Apparently a coterie of people in the inner Brooklyn camps of cool realized trying to be different was in fact still trying, and trying hard isn’t cool at all. The only cool thing left to do is to embrace the mainstream, ironically of course.

Un-natural selection

Evolutions of cool like this happen all the time. For instance, what does a hedonistic club hopper do when they realize they’re better than the suburban trash that frequent venues with vacuous names like “Glow”, “Fortune”, or “Trinity” (my personal ironic favorite). They evolve into “gypsies”. The gym evolves into yoga. Clubbing evolves into outdoor electronic dance music concerts. Short Prada skirts evolve into (still short) diaphanous dresses or just underwear. Black suits evolve into bear suits. Species evolve, and so does cool. Pretty sure Charles Darwin wrote that somewhere.

See in natural environments, a species’s success is often its ultimate downfall. Overpopulation leads to habitat destruction or starvation, a bunch of animals die, and the whole thing starts again. Much in the same way, in the world of cool, the only real stressor is ubiquity. Nothing adopted by the majority can be cool — nothing. Once everyone has or does something, that thing dies, and becomes incredibly uncool, until it can be reborn in some kind of douchey, ironic form.

Conclusion

In my experience, there’s one way to escape this cycle entirely. There’s one class of people I know who are cool regardless of their fashion choices, lifestyle, or demeanour: selfless people. Seriously — you want to be cool? Just be nice to be people. Care about what they have to say. Try to empathize with those you dislike even more than those you like.

This isn’t about moralizing at all. I’m not trying to say piety is cool. In fact, disingenuous empathy is terrible. It comes down to one simple heuristic. Cool people can handle themselves in social situations. The coolest person can parachute into any social gathering, whether it be some nerds playing Risk or a packed concert, and hold their own. People who are genuinely interested in others and their stories have an energy that draws others in.

So really what I’m saying is everyone at that party was right. Wanting to be compassionate or generous is actually pretty cool. And wanting to be cool, well, is not.

:’(