Bourdieu argued that his research was biographical: he sought to reflexively understand the social production of many of his life experiences without resorting to the illusion that they were unique, a-historical and transparent. To this end he systematically developed and applied a methodological toolkit, built around the concepts of field, capitals and habitus. Following Bourdieu's argument about the social-personal, I seek in this paper to focus in on the position of the headteacher. I argue that post-WW2, headteachers in England and Australia have pushed for more and more freedom and autonomy arguing 'I/we know what's best for my/our school. They [local authority, central office, politicians and policymakers] don't. If only they would give me/us the resources, stop interfering and leave me/us alone, we could just get on with it.' Mobilising Bourdieu, I sketch an argument that the quest for freedom is (re)produced as a disposition necessary for headteacher/principal practice in a de-and re-centralising schooling field. I offer this as a possible agenda for further research.