Purpose: This article aims to identify the main challenges faced by headteachers after taking up their first headship in the UK. It also compares how these challenges have changed over time. Other purposes include the setting of the initial phase of headship within a whole career model and how heads become socialised into the role. Design/methodology/approach: Based on evidence from empirical studies using longitudinal data over a period of 20 years, the paper reviews the challenges faced by new headteachers in the UK; it also advocates a stage model for studying the principalship. Findings: Many of the main challenges experienced by new headteachers remained the same over a 20-year period; most of the differences were accounted for by changes in government policy over the period. The main difficulties included catering with the legacy of previous incumbents, overcoming established school cultures and communication behaviours, coping with poorly performing staff, and countering a poor public image of the school. Originality/value: The paper uses the main longitudinal data set available on the challenges and difficulties experienced by beginning headteachers in the UK; it also contributes conceptually to the socialization of headteachers and suggests a stage model of headship, relating the beginning phase to a holistic perspective of headteachers' career trajectories. (Contains 1 table.)