In "The Pleasure of My Company," Steve Martin explores the complexity of self-expression and the pressure to conform to societal expectations. The protagonist grapples with the idea of authenticity, feeling uncertain about what it truly means to just "be himself." This reflects a common struggle many face when trying to align their inner feelings with external behaviors.

When advised to have fun with self-expression, the character's confusion highlights the challenges of navigating personal identity. The notion of enjoying oneself can seem vague or intimidating, especially when one feels disconnected from their genuine self. This scene captures the essence of the journey toward self-acceptance and the desire for authenticity in a world that often encourages performance rather than true individuality.