This qualitative study was motivated by a sizeable number of school principals retiring early in South African schools. They either leave teaching for other careers or retire before the retirement age of sixty. It was then necessary to explore what factors, if any, made them leave school management and the teaching career. Sixteen school principals were purposefully selected and interviewed through semi-structured interviews. Eleven of these had already left teaching in the previous four years, while the others were waiting for their last days in teaching at the time of the study. The results illustrate that there are various reasons that lead to the early retirement of school principals from historically black schools. Among these are burnout, lack of teacher commitment, increased unionisation of teachers as well as the non-involvement of district officials in the schools' improvement and management plans. Consequently, many participants maintained that it was almost impossible to run schools effectively when this scenario prevailed. The conclusions point out that school managers and leaders need to be supported in various ways as they steer various programmes in their schools. This includes constant mentoring, management preparation as well as continual formal professional development programmes.