This essay considers psychotherapy as creative endeavor on both sides of the therapeutic dialectic. It recalls both a Nietzschean adage (“self-creation, the most difficult art”) and the injunction he adapted ever-so-slightly from the Greek poet Pindar: “How one becomes what one is.” The presuppositions and potentials underwriting this piece tap into bedrock existential themes of transience and ultimate insignificance on one hand while holding out for possibility, some semblance of meaning within the void, on the other. These ongoing tensions elicit the apprehension and novelty that inhere in genuine exchange and the fashioning of character out of fragment, chance, and hard work. “Life,” Nietzsche observed, “is only justified as an aesthetic experience.” It is this feeling for the intrinsic, albeit difficult, place of self-creation (a beckoning of, and striving for, a Jamesean “more” or “ever not quite”) that serves as both touchstone and beacon in this reverie on psychotherapy and art.