To understand Nietzsche's pedagogy of self-overcoming and to determine its true import for contemporary education, it is necessary to understand Nietzsche's view of the self that is to be overcome. Nevertheless, previous interpretations of self-overcoming in the journals of the philosophy of education have lacked serious engagement with the Nietzschean self. I devote the first part of this paper to redressing this neglect and arguing for a view of the Nietzschean self as an assemblage of ontologically basic affects which have been guided and modulated by the incorporation of perspectives. This interpretation has important consequences for self-overcoming, for it constrains the individual's conscious agency to operations on perspectives. In light of this view I then advance a competing conception of self-overcoming and discuss some of the shortcomings of antecedent interpretations. Although previous interpreters have done their part to exhaust the characteristic actions of self-overcoming, I argue that they have either exaggerated the deleteriousness of social influence in the formation of the authentic individual, or else ignore it altogether. In the final part I reconsider the debate over the democratic or aristocratic nature of Nietzsche's pedagogy of self-overcoming. Interestingly, self-overcoming cannot be labeled strictly as either, and out of this ambiguity grows the role of the school as an agent of cultural transformation.