In recent years the UK secondary educational landscape has witnessed significant change, with the introduction of an ever-extending spectrum of competing government initiatives and policies. This has resulted in the steady erosion of the traditionally recognized role of headteacher. This paper presents the results of a practitioner-based study centred on the professional career journeys of a selected group of senior incumbent headteachers from across Liverpool, United Kingdom. The purpose of the research was to consider key features of difference in the headteacher role over a 30-year period. Five heads were interviewed about how they rose to headship and the influences and events that guided their career choices. Findings include acknowledgment of the requirement for self-directed career development, paucity of skills in preparation for headship, transformation in leadership models and the changing skills, qualities and qualifications required of contemporary and emergent headteachers. (Contains 5 notes.)