Why Being Uncool Is the New Cool
A guide to standing out in a world obsessed with fitting in
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Welcome to another edition of Beyond Self Improvement! If you missed it, here’s last week’s article: Navigating the Storms of Spiritual Life.
In today’s essay, you’ll learn the untold strategy that transformed a struggling salesperson into a top performer and how you can use it to overcome your hurdles. If you’re new, consider subscribing below to join our growing community and get the next essay direct to your inbox:
Dear Friend,
It’s unclear exactly what part of our brains distinguishes those who have “it” and those who don’t. But it seems an essential, almost primal instinct—and it doesn’t feel good.
By grade school, we start categorizing each other as “cool” and “uncool,” often by the most arbitrary standards. Our deep desire for personal acceptance is masked by our yearning to be one of the “cool kids,” where simply being part of the “in” crowd would satisfy our heart’s longing.
But it’s never enough. We’re never satisfied.
Being cool never brings the contentment we want—whether the right outfit, joke, or number of likes on a post. Instead of learning to appreciate these moments, we pursue acceptance with ever greater intensity. After all, validation from cool people feels fantastic.
The cycle continues because each moment of being cool fails to bring the joy, security, or sense of belonging we crave.
Rather than feeling closer to fulfillment, we feel more distant from ourselves, always believing we’re one praise away from genuinely being okay. While “hustling for love” (my favorite Brené Brown saying), we give up our sense of agency.
𑁍
Ultimately, trying to be “cool” is just a cover for our more profound need for love and acceptance.
It’s an outward desire of an inner longing for validation. Left unchecked, our attachment can become oppressive. Sadly, the desire doesn't end with high school—only the definition changes. Instead of listening to the right band, it’s about having the right job at the right company. Instead of having the right shoes, it’s about having the right car. Instead of using slang, it’s about having the right house in the right neighborhood.
Wanting to be "cool" has always depended on believing it was a prerequisite to being happy, but it had the opposite effect.
It led me increasingly away from who I was, acting in ways I didn’t want to act, saying things I didn’t want to say, and thinking thoughts I didn’t want to think, all under the misguided belief that happiness required being someone other than me.
In my relationships today (at least the ones that are healthy, mature and mutually satisfying), I’ve noticed that the more genuine and vulnerable I am, and the less I filter what I say and do, the more meaningful the conversations and the more I feel seen and understood.
Valuing fitting in and being cool above all else is a problem. Eventually, you feel trapped and can no longer bear your inauthentic existence. It feels like a mental straightjacket that keeps you guarded and in control, the one that doesn’t let you embarrass yourself at karaoke or be ridiculous on the dance floor.
Because taking off the straightjacket and being the passionate, vulnerable, silly you is way too risky.
𑁍
Here’s how to break free:
Look inside and have an honest conversation with yourself. What’s holding you back and why? Maybe you love watching ballet, but you’re worried your friends will think it’s weird. They may think you’re funny and stop inviting you to do things. Besides, it’s easier to like watching what they watch.
Tell someone about your fear. Sharing your worries is difficult and takes courage, but it may offer the perspective you can’t see but need to break free. Talking about your fears and insecurities may help you see how irrational they can be and begin the process of transforming your relationship with them. But words are not enough.
Face your fear. It’s time to show your friends how much you love watching ballet. But if you’re not ready, maybe this can help. At the core of uncool is risking being vulnerable. Being vulnerable is the choice to be authentic and let ourselves be seen. Here’s where it gets tricky—you must be prepared to be disliked. This is the risk we run when we reveal our authentic selves.
You’re safe with your friends, but for the general public, there will most definitely be people who will reject you.
The good news is, once you experience the joy and freedom of unleashing the real you, you see it’s worth the occasional hater. When you risk being yourself, you feel alive. A little scared, perhaps, but primarily alive
Before you think about this too much, there’s one more step.
It’s right there in the title. The only thing to do is be exactly who you are. It takes courage, and stepping out of your comfort zone will surely get you knocked around. But stay at it. Because one day, without ever realizing it, you’ll be beyond cool or uncool and just be you.
And just like that, you’re unique like everybody else.
𑁍
In the end, my longing for freedom overrode my desire to fit in.
The things I was made fun of the most that made me uncool—being skinny, shy, and nice—have fueled my success later in life and made me the person I am today. And I wouldn’t change that for the world.
Seeking approval from others has always been a roundabout way of seeking permission to accept who I am. It was as if I were asking for a glass of water when I could have just helped myself. Strangely, it didn’t have to be that hard. I could have chosen myself all along.
Accepting yourself as you are, "cool" or not, is one of your life tasks. When you learn to appreciate yourself and know that you belong, you no longer seek acceptance from others. You approve of yourself, and there’s no greater way to love yourself than that.
Keep being unapologetically you,
Ryan
Thank you for walking beside me on this path, my friend. I’m glad you’re here.
My biggest passion—working 1:1 with readers like you.
Whenever you’re ready, I can help you stop waging war with yourself and start being your best friend. Schedule a free, 45-minute discovery call now.
This is rich, articulate, and greatly appreciated. I enjoy how you have explored the issue of “cool vs. uncool.” It’s a subject I have often pondered. It’s amazing how it (the need to be perceived as “cool,” “hip,””with it,” etc) runs so many of our lives, often in the background, but it’s still there. Ultimately, the need to be seen as “cool” often shuts people out and causes us to create all sorts of ways of being in the world that don’t reflect who we truly are. “Coolness” is an epidemic! I “suffer” from its afflictions myself, and I’m happy you have reminded me of this. It’s ironic how, while the need to be cool is indeed rooted in the desire for love and acceptance, it actually often circumvents love and acceptance entirely. Thank you, Ryan!