The practice of personal autonomy is a dynamic event that consists of a vital interplay between the self, socio-cultural reality, meaning, and being epistemically responsible. Autonomy is not static, something that we simply possess by virtue of a status as 'rational beings'. Therefore, in this dissertation, I examine the traditional notion of autonomy as it has been developed by Kant and subsequently influenced the current debate between 'liberals' and 'communitarians'. Primarily from the standpoint of the critiques developed by Charles Taylor, I argue that the fundamental disagreement between these two camps is over the concept of the self. While this landscape stands divided, some middle ground can be found in the work of Joseph Raz, who postulated the need for a combination of individual abilities and an autonomy-supporting environment as necessary conditions for practicing personal autonomy. His characterization of 'personal autonomy', distinct from Kantian autonomy, forms the underlying paradigm for this work (although I argue that it must be expanded greatly). (Abstract shortened by UMI.)