This article reports on the changes that 15 vice principals experienced in their transition from teaching to administration. In-depth interviews were used to explore the personal change process that occurred, and data were analyzed for recurring themes to create a composite picture of this transition process. The findings illustrate that the novice vice principals experienced an intense socioemotional transition as they crossed organizational and professional boundaries. Former teacher roles and identities were diminished, and administrative identities and perspectives were normalized. The participants identified mediating factors related to change and transition phenomena, vertical and horizontal organizational socialization impacts, and inadequate role training and support. A visual metaphor of transitional epicycles, or cycles within cycles, was used to map the novices' experience of this transformational trajectory and their changes in perspective. (Contains 1 figure.)