This qualitative study examines the professional career-development experiences of 16 teachers holding administrative roles. The study focused on the quality and foci of the informants' experiences over time. Data were collected through in-depth interviews, to elicit the informants' life-story narratives. Qualitative content analysis was applied to the collected data. The findings indicate that the course of the teachers' career development included meaningful introspective, social, and cognitive experiences, as well as organization-related experiences. Also, it was found that there were three relatively distinct periods in teachers' professional career progression, each of which was characterized by a particular unique emotional experience. The research findings add new knowledge concerning the career path of teachers in middle management positions in the school's organizational system.