A promotion to vice-principal represents an important career milestone within the field of education. It signals an elevation in status, marks the culmination of years of teaching and preparation, and symbolizes the beginning of a new personal and professional journey. This study explored the trajectories of eight recently appointed secondary school vice-principals as they crossed the threshold between teaching and administration. It focused specifically on the nature of their transition, the factors that were significant in facilitating or hindering it, and the challenges, tensions and dilemmas they encountered in this process. A review of the psychological and sociological literature on change, transition and socialization was used to provide a perspective on the subjective and objective nature of the change and transition process, and a conceptual framework was derived to explore and understand these phenomena. Qualitative data was collected through the use of personal inquiry methods. These focused conversations created opportunities and space for the vice-principals to relate and reflect on their personal narratives of the internal and external trajectory across the professional landscape of administration.The findings suggest that the transition from teaching to administration is a complex developmental passage that disrupts the world of new vice-principals. Becoming a vice-principal involves changing physical locations, interacting with a wide range of constituents at the multiple levels of system arenas, and assuming different roles, responsibilities, behaviours and perspectives. The participants experienced additional challenges because of factors related to inadequate preparation for the role; a lack of training and support from their school district; competing expectations from multiple stakeholders; and the demands of the rapidly changing Ontario reform context. These changes triggered a paradoxical socio-emotional process that required letting go, holding on to, and reframing aspects of their former teaching orientations, values and identities. A visual metaphor of recurring epicycles is used to describe this iterative trajectory of change and transformation. This study recommends that ministry regulatory bodies, school districts, professional development providers and administrative professional associations co-ordinate efforts to address the problematic nature of this role and the long-range developmental needs of new administrators. It concludes with a discussion of the ways in which vice-principals' transitions can be facilitated at the personal, professional and organizational levels, and provides suggestions for future research.