This paper explores how the contradictions of neoliberal education reform and its companion, the self-made aspirational subject, are embodied by Sir Michael Wilshaw, former headteacher of Mossbourne Community Academy in Hackney, East London, through his leadership practices. Wilshaw creates powerful mobility and morality tales that pave over the contradictions and ambiguities inherent in the academies programme and Mossbourne's approach. Drawing on a larger study of Mossbourne, the paper focuses on how raced and classed pathological discourses are mobilised and inverted both by Wilshaw and policy rhetoric, cultivating compliance through a belief in the aspirational subject capable of transcending social structures. The paper argues that neoliberal academy reforms are not about autonomy, but the imperative to comply with centralised policy demands at the expense of democratic participation and accountability.