Teachers who have held leadership roles at the school, district, or provincial level have the potential to contribute to student and school success when they return to classroom teaching. The contrasting experiences of two teacher leaders who returned voluntarily to classroom teaching are analyzed using Owens's (2004) social constructivist theory of role definition. These case studies offer insight into a teacher career transition that has been considered infrequently in current research. As such, they may inform the decisions of district personnel, school administrators, and returning teacher leaders so that such transitions feel less like sliding down a snake and more like climbing a ladder.