My friend and I sang an a cappella rendition of Extreme's 'More

In the journey of life, there comes a time for every individual when the desire to be seen, to belong, and to be considered cool outweighs the call to authenticity. Ed Helms’ words, “My friend and I sang an a cappella rendition of Extreme’s 'More Than Words' at one of our football pep rallies in a desperate attempt to look cool. For a while, I wore pink Converse All Stars because I thought it made me seem daring and irreverent,” offer a glimpse into the human condition, that deep-seated yearning to be accepted and admired by others. The lengths to which we go in the pursuit of coolness often reveal our inner insecurities, showing how the desire to fit in can lead us to take actions that, in hindsight, seem self-conscious and perhaps even inauthentic. Yet, there is a deeper wisdom in this—something that the ancients understood well: the search for identity is a journey filled with trials and errors, and it is through these experiments with persona that we eventually come to understand who we truly are.

In the ancient world, the quest for identity was not new. The Greeks, for example, revered the process of becoming oneself. In Plato’s dialogues, Socrates often questioned young men about their actions and beliefs, encouraging them to look inward and understand the truth of their desires. The great philosopher Diogenes, who lived in a barrel, rejected society's norms and embraced his own truth, while the likes of Socrates and Aristotle debated the importance of virtue and character in shaping a life well-lived. Both men and women in these ancient societies experimented with the masks they wore in public, but the key lesson was always to peel back those layers to discover the authentic self. Much like Helms' experience with the a cappella performance and pink Converse, these ancient figures realized that to be truly “cool” or respected, one must first embrace authenticity, not the fleeting trends of society.

The story of Achilles, the hero of the Iliad, is a striking example of this journey toward understanding one's identity. Achilles, in his early years, was torn between his desire for eternal glory and his love for his friend Patroclus. When Patroclus died, Achilles had to confront his sense of self, realizing that his quest for honor and glory was not the true path to fulfillment—true greatness lay in the relationships and moments of genuine emotional connection. Achilles’ quest for honor, like Helms' search for coolness, initially led him down a path of self-exploration, but it was in reconciling his true self with the roles he played that he found his ultimate purpose. His experience teaches us that while external validation may be sought in youth, true fulfillment comes only when we recognize and live out our authentic selves.

Even in the more modern world, we see this constant interplay between external expectation and self-authenticity. Steve Jobs, for instance, wore simple black turtlenecks and jeans, which contrasted sharply with the lavish, flashy outfits often worn by other tech moguls. In his youth, however, Jobs experimented with different personas, trying to figure out how to present himself to the world. What he ultimately learned was that innovation and vision were his true sources of power, not the trappings of what society deemed fashionable or “cool.” His legacy, like that of many in the ancient world, shows that the journey toward self-realization is often paved with experimentation and missteps but leads to a deeper understanding of one’s place in the world.

The lesson in Helms’ anecdote is not simply about the pursuit of coolness or the superficial choices that many of us make in our youth. Rather, it is a reflection on the impermanence of external validation and the transience of societal trends. Just as Helms later reflects on those youthful choices with a sense of humor, we too must realize that the things we do to gain acceptance are often not who we are at our core. The process of growth involves discerning between the masks we wear for the approval of others and the essence of who we are beneath. True coolness—as it turns out—is not about following trends or conforming to external expectations, but about the courage to stand authentically in one’s own skin, knowing that true strength lies in self-awareness and self-acceptance.

In practical terms, this means that we must embrace experimentation in our lives, understanding that we will make mistakes and try on many different roles as we search for our identity. Much like the great figures of history—whether Socrates, Achilles, or Jobs—we must allow ourselves the freedom to explore and grow, knowing that every trial, every attempt to fit in, is part of the journey. We must challenge ourselves to step away from the masks of social pressure and external approval and instead focus on cultivating the qualities that define us truly—compassion, wisdom, creativity, and authenticity.

The message is clear: be patient with yourself as you navigate the complexities of life’s journey. You will wear many hats, try on many identities, and sometimes chase the fleeting ideals of coolness. But in the end, the wisdom lies in knowing that true fulfillment comes not from external approval but from living genuinely and being at peace with who you are, regardless of what others may think. Like Helms, who now smiles at his youthful experimentation, we too will one day look back and realize that our coolest moments were those when we found the courage to be true to ourselves, to shed the masks of society and stand unapologetically in the light of our own truth.