This study compares Christopher Bollas's theory of thinking and the creative process, both within and outside of the psychoanalytic encounter, with the work of artist and sculptor Gabriel Orozco. It demonstrates the parallels between the psychoanalytic quest for the true self and the artistic endeavor to create art that offers a potentially transformative experience. Orozco's art and Bollas's psychoanalytic theories are inter-animating and mutually reinforcing, giving a discursive and visual form to ideas concerned with the fully-lived life and the search for personal truth.