This article considers career decision making in relation to headship/principalship. It explores the career options open to experienced and promoted teachers. Changes in the role of the headteacher and perceptions of the role of the head held by potential and recently appointed headteachers are reviewed. Findings on acting headship are used to illuminate headship itself and recruitment issues. Headship is analysed in terms of factors at four levels: the system, headship itself, the school and the individual. The outcome of a recent major inquiry into teachers' pay and conditions in Scotland and changes subsequently agreed is analysed for its likely impact on the nature of and recruitment to headship. The article concludes with some thoughts on the need for sufficient but not excessive numbers of good applicants for headship, for effective human resource management of teachers and potential heads and for shared realism about the role of school leaders.