This article provides an analysis of issues related to personal "dignity" and social validity in schools. Specifically, dignity is defined in terms of individual success and independence, while "social validity" is defined in terms of the system as a whole. These definitions are explored in the context of schoolwide systems of positive behavior support (PBS). Descriptions of schoolwide systems of PBS are used to analyze and detail procedures that maintain respect for personal dignity and social validity. In addition, processes for engaging persons in this discussion are critically analyzed. Future development and growth of PBS as a technology-based approach to developing self-determined, independent, and successful persons is discussed. Direction is suggested in the way we consider issues, define our values, and engage others in systemic change efforts.