This article analyzes the career trajectories of eight Black and South Asian headteachers who were part of a larger study of three generations of Black, Asian, and Minority Ethnic (BAME) headteachers (28) interviewed in 2015 (Johnson, 2017). Using a longitudinal life history approach and portraiture, it seeks to answer the question, "How do Black and South Asian headteachers narrate their career progression and leadership values over time?" In particular, I explore the growth of academization and the formation of Multi-Academy Trusts (MATs) on the work lives of Black and South Asian headteachers and the role of autonomy, value alignment, and professional support on their leadership retention.