This study investigates the experiences of a group of classroom teachers who transitioned into administrative roles as vice-principals in a rural schoolboard in southwestern Ontario. We included both elementary and secondary former teacher leaders who moved into the school administration and explored the aspects of their leadership experience that influenced their decision to make the transition into an administrative role, the challenges they faced, and how their formal and informal leadership experiences prepared them for their responsibilities within their new role. Eight former teacher leaders who moved to the vice-principal role within the last two years were interviewed using semi-structured interviews. The data were analysed using a two level coding strategy that allowed for the identification of key themes and patterns. This study found that (1) increased responsibilities and professional growth were motivators for teacher leaders to enter into administration; (2) while that there was a rapid adaptation entering the new job, the teacher-leader experience did not prepare them for the feelings of isolation from their former peers in their new role; and (3) establishing professional and collegial relationships with staff and community members is central to the successful transition from teacher leader to administrator in a rural context. This research aims to inform further research in the area of transitioning from teacher leader to administrator as well as future recruitment and support initiatives for aspiring leaders in rural schools.