There's nothing less funny than someone who looks cool. There's

"There's nothing less funny than someone who looks cool. There's nothing more unappealing." With these words, Eric Wareheim strikes at the heart of an ancient paradox—how the pursuit of coolness often leads to the loss of what is truly authentic and relatable. This idea, while expressed in modern terms, echoes the wisdom of the ancients, who understood that true humility, vulnerability, and genuineness are what resonate most deeply with others. The more we strive to appear impressive or untouchable, the more we risk losing our connection to those around us.

In ancient Greece, Socrates famously challenged the notion of outward appearances. He believed that true virtue and wisdom came not from outward displays of grandeur, but from inner reflection and understanding. Those who were obsessed with being seen as powerful or important were often the least interesting, he argued, for their focus was on self-presentation, not on the value of the soul. It was the humble, the self-aware, and the willing to laugh at themselves who, according to the ancient philosophers, were the most appealing. The pursuit of coolness was an empty endeavor that could never lead to true greatness.

Eric Wareheim’s words reflect this ancient wisdom, pointing out the unappealing nature of someone who tries too hard to be cool. In truth, coolness is often a mask, one that hides a lack of substance or a fear of being seen for who we truly are. Consider, for instance, the famous Emperor’s New Clothes tale, where an emperor’s obsession with looking grand and dignified led him to be paraded about in nothing but his vanity. His desire to appear untouchable, powerful, and cool left him vulnerable to ridicule. Only a child, untainted by the emperor's desire for grandeur, could speak the truth. The emperor's lack of self-awareness made him the most laughable figure, not the least.

Real-life figures who possess a balance between humility and confidence are often those we admire most. Take, for example, Leonardo da Vinci, whose brilliance in art and science was renowned, yet he lived not in the pursuit of fame or glory, but in a quiet, relentless quest for understanding. Da Vinci was not concerned with looking cool; he was driven by curiosity and a deep commitment to his craft. Those who met him spoke of his unassuming nature, even though he was revered by kings and scholars alike. It was his authenticity that made him appealing, not the act of putting on a persona of grandeur.

In contrast, consider the rise of the vain hero, who seeks only to shine in the eyes of others. The ancient tragic heroes, like Achilles, were often undone by their pride and their desire to be seen as invincible. Achilles, though revered for his strength and valor, ultimately faced his downfall because he could not relinquish his need for glory. In his pursuit of coolness, he became isolated, and his inability to embrace his own vulnerability led to his untimely death. True greatness, the ancients taught, lies not in being perfect or unattainable, but in accepting one’s imperfections and humanity.

The wisdom here is profound and deeply relevant to our own lives. Coolness, when chased for its own sake, often leads us to alienate others and, in the end, to feel empty ourselves. The more we try to be something we are not, the more we lose touch with who we truly are. In contrast, the most appealing people are those who do not take themselves too seriously—who can laugh at their own foibles and embrace their imperfections. The funniest, and thus most beloved, are those who do not need to appear cool, because their genuineness shines through.

So, the lesson we can take away is clear: stop chasing coolness. Instead, embrace your authentic self—flaws, humor, and all. Do not hide behind a mask of perfection or an image that others may admire. It is the imperfect and the vulnerable who connect most deeply with others, for they offer something real in a world full of façades. Laugh at yourself, be authentic, and embrace the messiness of life, for it is this that will make you truly appealing. True greatness lies not in appearing cool, but in being real, and in the power of humility and laughter to break down the barriers we so often erect between ourselves and others.