Perspectives on freedom, liberty, agency, creativity, and free will have a rich and varied history in philosophy, psychology, neuroscience, and psychoanalysis. Central to psychoanalysis, we want nothing for our patients, nor from our patients, if not the expansion of their personal freedom, agency, individuality, creativity, and self-ownership. What is freedom, exactly? What does it mean to have and to exercise free will? What does it mean to be truly creative? Do we have true choices, or are we overdetermined puppets faltering under the illusion of self-generated acts of freedom? Does feeling free to choose, and then perhaps acting to choose, equate with actual freedom? These perspectives and questions are examined in light of how we think about emotional health and the phenomenology of therapeutic action. This article explores an emergence theory of free will and the centrality of self-ownership in understanding and experiencing freedom of choice. A clinical example is offered in the spirit of what it might look like and what it might mean to enable authentic free choice.