Scholars believe that accumulating experiences of self-alienation and falsehood urge us to reshape our selves, sometimes through experimenting with different ways of being and acting, often leading us to developmental leaps. In this paper, I examine analytic therapists’ struggles to reshape their professional selves and suggest three ways in which supervision can facilitate this process: a. Fostering the supervisees’ internal dialogue between different therapeutic voices including those of their supervisors. b. Constructing and consolidating the supervisees’ “future selves;” how they envision themselves as therapists in the future. c. Constructing and facilitating supervisees’ experimentation with different versions of the self on the prelinguistic and linguistic levels. Furthermore, I discuss the challenges in assimilating the supervisees’ professional developmental leaps, which often result from such processes.