how to be cool
the counterintuitive nature of coolness
Coolness stems from individuality. Think about anyone ‘cool’ you notice on the street or meet at a party. They’re not cool because they seem vaguely like someone else you’ve met before. They’re cool because they are themselves. They are cool because they are (1) somehow different from everyone else, and (2) they lean into their difference. We all crave being true to ourselves. And when we see someone out there doing it, we think: fuck, that’s cool.
coolness comes from within
There’s this common notion that everyone’s enlightened, they just don’t know it yet. My interpretation of this is that we all have the seed of self-actualization inside of us, even if we haven’t captured it yet. What usually keeps us from accessing it is ourselves.
The journey of life is a continuous process of getting out of your own way because only you know exactly how to obstruct yourself from your own process of becoming. This is the nature of Resistance—it is our inner intelligence working against us. It’s the friction we face while self-actualizing.
From my previous essay resistance & regret:
Resistance is a dynamic force equipped with all of the self-awareness and intelligence we ourselves possess. It is trained off of a data set complete with every single one of our past decisions, vices, weaknesses, strengths and it uses this information explicitly to sabotage us.
Our Resistance is like a super-villain designed to prevent ourselves from levelling up, expressing ourselves, bringing our ideas to life—knowing everything we know about ourselves, and using it all to get in our way. It is us turned against ourselves, in the truest sense. This is why the journey to the self is one of continuously outsmarting our Resistance, of breaking through each upper limit tethering us to past versions of ourselves. But the ultimate way to ‘outsmart’ Resistance is not to fight it, but instead to lead from a place of stillness. To quiet your mind when it speaks up, and bring yourself back to the moment. Because when we get too cerebral about anything, it becomes nearly impossible for us to break through to action.
Perhaps by now you’re wondering: but how does this relate to coolness? Because coolness is just a byproduct of knowing who you are, and being cool with it. Put simply: it’s self-expression. Achieving it isn’t as simple as it sounds, though. That’s why there are several multi-billion dollar industries designed just to sell the product of “being cool.” Mimetic theory and status games revolve around one primary currency: being admired by others. People pay a lot for admiration, especially if they haven’t yet accepted themselves. We often foolishly think the acceptance we seek can be found externally (spoiler: it can’t). When we start seeking ‘cool’ outside of ourselves, it’s time to look inwards.
first we imitate, then we intuit
The thing about coolness is that you don’t start out knowing how to be cool, because you don’t start out knowing what you like. You start out—as we all do—by imitating. The very first thing we do when we are babies is imitate. We look at adults sticking their tongues out at us, and we do the same. This extends to early childhood. One of our friends is playing with Yu-Gi-Oh cards or Polly Pockets, and we think: hey those are cool, I want some. So, we collect and collect and collect. Then we shed. We keep the stuff we actually spend time with, the stuff we truly enjoy. This is when we start fixating on the things we especially like—this is how we develop taste! It’s the stuff we keep, not because we think it will seem cool to others, but because it’s cool to us.
This is why we have the saying that “the people that were cool in high school never end up all that cool later in life.” The cool kids at that age were just really good at imitating, which was the currency of coolness then. Since everyone was floating in a sea of imitation, no one appreciated individuality. The opposite in fact: they punished it. The kids who were unapologetically themselves were called “weird” even though they were just getting a head start on their future coolness by having a clear sense of self—and thus: a clear sense of taste!
We all eventually grow up and realize that imitation as a means to achieving coolness leaves you in pretty rough shape—largely trading your life, time, and freedom for what is considered “cool”. Taking jobs because they’re prestigious, instead of because they are in alignment with you. Spending money on objects, experiences, and status symbols that signal pseudo-coolness instead of expressing your individuality. Then getting confused when you don’t fully embody that oh-so-elusive-coolness. But the reason you’re not cool is because you’re trying to be cool.
the coolness epiphany
I had a dream the other night where I was hanging out with old friends, ones I spent time with back when imitation was the best way to grasp at coolness. We went to parties. Dressed up. Painted our eyes with eyeliner. Wore push up bras. We did what we thought was cool (because that’s exactly what you do when you’re young and figuring yourself out!)
In this dream, we were transported back to being newly minted teenagers who were just trying to be cool, but my state of mind was where it is now, and theirs was stuck where it was back then. They wanted to do what everyone else was doing. Go to the places where the “scene” was. Do what was ‘cool’. Confused, I asked: why don’t we just hang out with each other, skip the “place to be” and just be here? Everything we need is right in front of us. But they were so attached to the idea of doing what everyone else was doing that they became blind to what we had. And for the first time, I felt distinctly repulsed by this attitude towards coolness, because I saw just how backwards it was.
There was a key difference between me and the people in my dream: they hadn’t had their coolness epiphany yet. I believed being cool was being yourself and being with your people. They thought coolness was portraying yourself as someone ‘cool’ around people you wanted to impress. This was only a dream, of course. But it was reminiscent of how I felt when I was younger, when I started to pick up on the fact that imitation wasn’t the true root of coolness, but a cheap attempt at copying it. The true root of coolness lies within. Matthew McConaughey captures this sentiment beautifully in the following quote (please read in his voice for full effect):
“Cool is a natural law. A fad is just a branch on cool’s trunk. A fashionable fling whose 15 minutes can never abide, no matter how long it tries. Cool stands the test of time. Because cool never tries. Cool just is.”
Cool just is—because coolness comes from being comfortable with yourself. And when you’re comfortable with yourself, you just are. You aren’t worrying about what others are going to think or “where the people are.” You just want to be where you are, where your people are, where you can be yourself—because what could be more cool than that?
the path to coolness is paved with self-acceptance
The irony of coolness is that people are always looking for it in exactly the wrong places. They look around at others, at what is “in” and then they express that. But as McConaughey points out, cool never tries—cool just is. The cool that people seek through imitation—trends, status symbols, prestige—doesn’t last. Coolness is one-of-a-kind wherever it is found, because it is a product of self-knowledge and expression. Any attempts at mirroring coolness fall flat, because you can immediately tell if the person is comfortable with themselves. And when they aren’t, it’s clear the coolness they are trying to express is a performance rather than their existence.
trends try, cool just is
One example I always chuckle about in my head is a feature of mine that, over the past few years has garnered more compliments than probably any other one: my eyebrows. People (mostly women) often come up to me and say: wow, I love your eyebrows! or, my personal favourite: are your eyebrows real? I laugh a little, politely affirm that they are real, and say thank you. I laugh because my eyebrows have always looked like this. Ever since I was a child, I had thick, dark, pronounced eyebrows. Back then it wasn’t cool, though. Thin eyebrows were in. My eyebrows were the opposite of cool—it was probably odd to anyone tuned in to trends that I left them so thick, that I didn’t change them to match the trend. But eventually that trend passed, and thick, dark eyebrows became the new flavour of cool. Suddenly, people started asking me if my eyebrows were even real, because people were altering their eyebrows to make them thick and dark, just like mine.
The irony, of course, is that as soon as thin eyebrows are back in, I’ll probably get those nostalgic, confused looks from the people that complimented me. They will ditch their newly minted eyebrows to fit back in with what’s cool, and look to me with confusion as to why I’m not doing the same. But my eyebrows will (hopefully) always look like this. I don’t plan to change much about my appearance if I can help it. Because trends come and go. They’re in, then they’re out. All that effort and money and damage to ourselves to keep up with them.. and for what? To be cool, just to realize that cool doesn’t try, cool just is.
pursuing cool only confuses you
Sometimes we need to take the long way home on these life lessons—but let me spoil the end of this coolness journey for you. Conforming to what is in, or what you think people will think is cool, just makes you more confused about who you genuinely are. Self-acceptance is the natural source of coolness. It is a renewable resource. The more you accept yourself, the cooler you become. Trends are non-renewable—any coolness you source from them will expire—and you will be forever stuck looking for something new to imitate. When you learn that the coolest parts of you are the parts you are covering up with the stuff that you think makes you cool, you’ll shed everything and just be yourself.
Let your life reflect your true self. Lean into the quirks in your style. Let your interests roam free. Be passionate about what you love, about who you love. Lean into your weird. Say what you want to say. Do what you want to do. Feed your curiosity. Befriend the people you actually align with, instead of “cool” people that hold social signal value.
coolness is your inner truth, expressed
Coolness comes from within. It starts with self-acceptance > which leads to individuality > which leads to the development of taste > which leads to self-expression > which is the essence of coolness. We cultivate coolness by going inwards. When you’re being your true self, cool radiates off of you in waves. People sense it immediately and ask you how you do it. You shrug and say you’re just being yourself. Because there are no shortcuts to coolness. There is just the process of becoming who you truly are. Your existence is the essence of your coolness. So, try less. Be more. Your coolness will come naturally :).
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Until the next essay, you can find me on Twitter, in the comments of this essay, or via my previous essays here. If you liked this one, you may also enjoy compatibility and connection.
Nailed it, so good.
My favorite way to describe the Write of Passage journey to new students is “Write the articles you can write. Pursue the (career) path only you can pursue. Live the life only you can live.” Maybe next time I’ll save my breath and say “eh just be cool”
Everyone wins on their uniqueness and everyone’s insecure about their uniqueness.