This is an examination of the processes and procedures involved in developing a career in teaching and becoming a secondary headteacher in England. Looking at the experiences of a group of secondary headteachers in two local education authorities, the author compares how career structures match up to actual experiences of promotion. She explores gender differences in experiences of headship and considers how changes in education in the UK have affected headteacher careers. She argues that teachers can take positive action in their careers to work against the constraints inherent in the system.