When I was fifteen, I dreamed of living in the big city, as many

The words of P. J. O’Rourke are veiled in humor, but within them is a truth as old as the restless human heart: “When I was fifteen, I dreamed of living in the big city, as many a young person does if he is artistic and sensitive. By ‘artistic and sensitive’ I mean short, skinny, unkissed, bad at sports, and carrying a C average in high school.” This confession, though cast in laughter, reveals the eternal yearning of the outsider—the one who feels ill-fitted to the ordinary mold, who dreams of escape into a place where strangeness may blossom into strength.

He begins with the image of youth at fifteen, that turbulent age when identity trembles like an unsteady flame. At this age, many feel inadequate, awkward, unformed. The short, skinny, unkissed, bad at sports child is not merely a caricature; he is the symbol of all who feel cast to the margins. O’Rourke calls such a one “artistic and sensitive,” not in mockery, but in recognition: for the soul that does not triumph in games or grades often seeks refuge in imagination, in art, in the dream of elsewhere.

The dream of the big city is the dream of reinvention. Villages and small towns bind us in the gaze of neighbors, where every stumble is remembered, every weakness magnified. But the city, vast and impersonal, promises freedom. It whispers to the youth: “Here you may cast off the labels of your past. Here you may become who you are.” Thus, the sensitive soul, battered by failure or neglect, looks to the city as both sanctuary and stage.

History gives us countless examples. Vincent van Gogh, awkward, often rejected, and burdened with loneliness, left behind his provincial life to seek meaning in Paris, where color and light reshaped his vision. Though he did not find worldly success in his time, his art—born of that restless longing—became immortal. So too did countless poets, writers, and musicians leave behind the scorn of their youth to find in the city a place where their strangeness became their strength.

O’Rourke’s wit reminds us also of humility. He admits to a C average, as if to say: greatness does not always announce itself in classrooms or gymnasiums. Many who falter in youth’s measures rise in adulthood through persistence, creativity, and vision. The standards of adolescence—height, charm, popularity, athleticism—are fleeting. What endures is the fire of curiosity, the willingness to dream, the resilience to seek one’s place even when uncelebrated.

The lesson is profound: do not despise your awkward years, nor measure yourself by the narrow judgments of youth. What makes you different, what isolates you, may be the seed of your destiny. The outsider who dreams of escape may one day shape the culture of the very cities he once imagined from afar. For the pain of not belonging sharpens the vision of what could be, and that vision births art, satire, invention, and greatness.

Therefore, children of the future, remember this: if you find yourself short, unkissed, clumsy, or overlooked, do not despair. These are not curses, but the chisels that carve your character. Let them drive you to dream, to seek, to create. Your weakness today may be the foundation of your strength tomorrow. Do not run from your difference—carry it boldly, even humorously, into the world, and you will find that what once marked you as small may mark you as unforgettable.

Thus, O’Rourke’s words, though wrapped in comedy, reveal the eternal: greatness often begins in awkwardness, and the dream of escape is the first step toward becoming who you truly are. The city may not always grant you fame or fortune, but it will grant you the chance to transform your strangeness into song, your failures into wisdom, and your sensitivity into light for others.