In our opinion Jonathan Lear is one of the most significant American thinkers in the first decades of the 21st Century. In his brilliant and seamless fusion of philosophy and psychoanalysis he has presented such a startlingly original concept of the human psyche and what is comprised in “a distinctively human life” that it constitutes a novel and compelling human ontology. We present this ontology by attempting to unify Jonathan Lear’s ideas from his first great psychoanalytic work, Love and its Place in Nature, through his most recent work on irony and psychic integrity. We explicate Lear’s brilliant reformulation of Freud’s theory of development, his critique of the Western attempt to overly organize the psyche to defend against psychic and social disruption, and his postmodern advocacy of “living without a principle.” We conclude by showing how developing the virtues of courage and hope with a disposition to irony are the keys to becoming a person who can integrate the disparate parts of the psyche, engage in meaningful self-inquiry, and live in a vibrant openness to new possibilities. In sum, we attempt to show through Lear’s work that it is only by living with both a psychoanalytic knowledge of the depths of the psyche and ways to access this depth that one can realize the possibilities of one’s humanity to the fullest degree.