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There is a dearth of literature about the career life courses and voices of Deputy and Assistant Headteachers in secondary schools. This thesis examines the career trajectories and the experiences of Headship from 14 Deputy and Assistant Headteachers in secondary schools in Birmingham, England. A two-phase, mixed-method study (survey and semi-structured life history interviews) was employed as part of an explanatory sequential design. This research builds upon previous work in life history studies along with career phases and stages research. The findings from this study add new insights to the senior leadership role and the perception of Headship in that the Deputy and Assistant Headteacher career stage and socialization experiences can determine whether they stay, leave or climb the career ladder to Headship. This thesis tentatively suggests that Deputy and Assistant Headteachers lean towards displaying mainly Bonder, Bridger or Leaver characteristics that contribute to aspiration and how they utilize their social capital in their career journeys. A new career stages and phases framework pertaining to Deputy and Assistant Headship in secondary schools has been forwarded which draws on the distinction between bonding and bridging social capital and career transition in school leadership and management.