Cool Self

A theory of life about searching for your best.

Am I cool? What is cool? Is it ok that I’m thinking about what’s cool?

We all go through life asking these questions. Usually we stumble upon some theory of life that doesn’t answer them, and instead prompts us to ask different kinds of questions. But I think that’s where the usual, often inscrutably deep theories of life miss the mark. Recently I’ve landed on my own theory, one rooted in a kind of common sense, one that answers some of my questions about cool.

The theory, in brief: Life is about finding your cool self and then living as much of it as you can being that person.¹

II

You might be wondering what one’s cool self is. 

In my simplest definition, it’s the version of you that feels like you’re being yourself and feels cool. Naturally, this hinges on how we define cool. So in the fewest words I can muster, cool means being authentic, confident, calm, and original. 

Authentic meaning being yourself, not pretending to be someone else. Confident meaning self-assured, trusting your own beliefs and decisions and actions. Calm meaning being unphased, exhibiting a nonchalant attitude towards noise. And original meaning there’s a felt uniqueness to you, your thought, your expression. People who are “cool” are, in the ideal state, free from something others are not.

Traditionally we think of “cool” as a judgment made by others. People think you’re cool; you don’t call yourself cool. This irks some people: the mere idea that what society thinks about us carries any weight at all is taboo. We like to preach that the best way to live life is without any regard for what others think. But this is idyllic; it’s not at all pragmatic. Caring what others think is a universal social behavior.²

At the same time, coolness is not just about outward appearance or perception or social status, as people have come to label “cool” as being about. Cool is also something you feel about yourself. There are times I feel cool, and there are times I definitely do not. Cool is as much a matter of self-identity as it is of projection.

So how do we reconcile the two? It’s a hard task.

Like beauty, there’s an inner cool and an outer cool. Inner cool is closer to self-worth and self-actualization; outer cool is a never-ending game of belonging and status. Ideally, you want to focus on cultivating the inner cool, make it spill over into the outer cool, and live in that state of being as much as you can. Coolness at its best is the felt harmony of self, social, and societal respect.

III

Anyone can be cool, but everyone can’t be every kind of cool.³

There are tradeoffs in the kinds of cool you can be; some kinds of cool have overlap with each other and other kinds of cool exist in isolation. In an economic sense, your cool self is also a matter of comparative advantage. Every kind of cool is unique. Each person is more likely to be unique in one way than another. So find that thing most likely to maximize your feeling of cool — ikigai but for finding your cool self.

Being your cool self is not mimicking some persona popularized in culture or meant to please your target. (The affected “cool girl” of Gone Girl fame for example or the “cool guy” of classically masculine movies of past). Being your cool self should not be striving to be some standard archetype of cool. Yet, there will always be threats trying to push you from your cool self to cool someone else.

There’s always tension between personal cool and societal depictions of cool. And it’s scaled infinitely by the global attention game. With digital identities and the mimetic weight of social media, the archetypes of cool change with the oft fickle cultural winds. And coolness is neither constant across cultures nor monolithic.

So you have to choose your cool. Your cool self should be an identity that aligns with both what you want to be and feel is true to yourself and that you can successfully express to the world. And perhaps controversially, it should come with some feeling of social acceptance, even if just from a niche group that only you care about.

IV

The theory of the cool self extends to one's ambition too.

Much of ambition is just a quest to become a cooler version of yourself (or what you think will be or feel like a cooler version of self). The destination the ambitious are searching for isn’t always something so concrete as money, power, fame, influence, or the ability to buy things; it’s a feeling of accomplishment and satisfaction that gets you closer to cool.

When you ask a little kid what they want to be when they grow up, what is their answer based on? When they answer astronaut, doctor, actor, basketball player, YouTuber, it’s not based on a deep understanding of their own psyche, the job, the lifestyle. It’s a gut reaction based on what they marvel at, what they find cool. And more often than not, what’s been marketed to them as cool in some fashion.

Are adults different? Somewhat. Adults have the benefit of learning about themselves and the world to a far greater extent. A smart adult with the powers of introspection can far better rank their choices of cool and add personal interest and pragmatics into the equation that ultimately determines their life path. But make no mistake, they’re still not immune to the allure of cool. (Be honest: how often have you loved doing something versus just loved having done or been something?)

Everything you do — that you give your attention to, embrace, embody, champion, consume, create — is better when it’s cool.

Is it a stretch to say that everyone’s ambition is to realize their desired identity, and that this identity is just their cool-est potential self? I don’t think so. But I do insist that the journey towards your cool self must be authentically you. Beware of finding yourself just chasing outer cool, as ambition so often spurs humans to do.

V

Profound relationships are born from your cool self too.

People say being in love, being loved, is the peak experience of life. That no matter how much we can quench our desire for money, fame, power, lust, greed, and all the other vices, that attaining true love supersedes them all. And I think there’s a lot of truth to this. 

I also think being your cool self is an integral step in this kind of love. Sure, your family may love you whether they think you’re cool or not. But love that originates outside the family has a lot to do with cool. I’d posit that romantically liking someone always involves thinking they’re cool (though this ‘cool’ can be of many kinds). Loving someone is arguably thinking they are one of the coolest people you know, if not the coolest, just for being themself.

When new romantic love morphs into a kind of steady companionship, you might lose a bit of the attraction that exists only between two naive cool selves. When people talk about how to keep relationships lively, fresh, they suggest doing new things together. Why? New things are new opportunities to show your cool, an avenue to continuously refresh your ability to impress and appreciate the other.

Belonging to any community or social group is heightened by feeling like your cool self too. When your friends think you’re smart, stylish, fun, they think something about you is cool. And when you see them as true friends, it’s because you both feel like yourself and feel cool around them. Sure, you can feel accepted on the basis of some criteria, for being useful to people, for just being welcomed regardless of who you are. But many deeper bonds form between two cool selves.

VI

I’m my coolest self in the company of people who put me at ease.

I’m one kind of cool around my closest family. I’m a slightly different kind of cool around people who I’m not yet entirely complacent with, yet I trust and want to impress a bit (because, for some reason, I already think they’re cool).

I’m my cool self when I’m wearing something I feel cool in, that represents my tastes and stokes my confidence. I feel my cool-est self when I’m energized by something I’m working on, something I’m creating that I care about, that I’m proud to share with the world, and that if successful, will compound value for me. 

I’m my cool self when I’m not burdened by anxieties about the future or the past and am actually in the present. When I don’t second guess myself and I express my opinions and personality freely, without too much regard for propriety. When I’m in an environment that puts me at ease: low lights, comfy chair, cozy space in a familiar place or a new one that already feels homey.

New York City seems to have many people being themselves while exuding some kind of cool. It’s a place that people who want to be individuals, to achieve and express something unique about themselves, seem to seek out. Yes, I’m certain there are phonies and automatons here too. Some people fall into conformity, into being too quintessentially NYC, but optimistically I think many stumble in the other direction — into being a cooler version of themself. Being cool isn’t location-dependent, but a certain city or environment can unveil more of the cool you.

VII

If you haven’t found your cool self, you have two options: 

Change something about yourself or change something about your environment. Changing something about yourself can be changing something tangible or just how you express who you are in the world. Changing something about your environment can be the people, the place, the culture, a lot of things. 

The idealistic thing to say is that people never need to change who they are. This too is one of those good foundational principles, but changing yourself to get closer to the emotional self-actualization that your cool self represents is — I’d argue— good for you. And the truth is that what feels like yourself and what feels cool, to you and to those few people whose opinion you care for, will always evolve.

I’m not saying that the only measure of living a great life is finding your cool self. For one, there’s more to dissect in our relationship to cool and the dangers of measuring your self-worth in any capacity that clings to an identity (this likely merits a whole other essay about the psychology of desiring cool). And there are undoubtedly basic necessities and other values to cultivate in life, to guide important decisions and relationships and the like, in good times and bad. But no matter what you’re facing in life, I’d propose that facing it as your intrinsically cool self will yield better results and more “happiness” as we generally think of it.

Perhaps that’s why everyone chases the feeling of cool. The search for cool is a search for your best self and the best version of those around you. A cool person knows what they want and does what they want, and they do it with authenticity, confidence, calm, and originality. So in a world that demands masks and performances, that hammers you with mixed-media messages of the current kind of conformity, finding your cool self is a triumph. And admittedly, it can be hard.

That’s why the theory of the cool self is grounded in common sense. It isn’t inscrutable for the purpose of seeming deep, seeming complex enough to be considered a serious theory of life. Its seriousness lies in the fact that it’s intuitive, that you know it when you feel it (and most people have felt cool at some fleeting point in their life). The seriousness of the theory of the cool self lies in its simplicity. 

Find your cool self, and live in it.

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Special thanks to Bharat, Ashwin, Sam, Srijan, and Angela for their feedback on a prior draft of this piece, shared in Writers Block.

1. I’m sure this will strike some as superficial, low-brow, or whatever dismissive label you could conjure up. On the one hand, I could make a case that it’s none of these things. And on the other hand, I could make a case that it’s all of these things, but then so is every other theory about life. No one has a definitive answer to the purpose of life or the ultimate experience of living it. All any of us have is a theory. And just because “cool” has been inundated with superficial meaning, I don’t find it any less significant.

2. Take “purpose.” We all seem to agree that purpose is worth searching for. We say purpose is found in dedicating yourself to some kind of work, taking on a respected role in a community or profession, one that’s inevitably in service to others. This gives people purpose, meaning, satisfaction, fulfillment. Doesn’t this depend to some degree on others’ opinions and judgments of you? Unequivocally, yes.

3. “Cool” is one of the most abstract judgments introduced to us very early in life. When you’re young, the categories of cool seem limited. As you grow up, the categories of cool get more diverse (and we start using different, more nuanced words to describe “cool” too). At the same time, what it takes to fit into these categories of cool becomes more specific and more merit-based. Perhaps this is why we observe that many of the “cool kids” in high school peak in high school. A lot of that is outer cool. And the incentive to work for cool can be weak when you’ve already tasted it for free. It’s those who haven’t tasted it much that seem to maintain the drive.