As part of a doctoral study examining how social justice is understood and acted upon by educational leaders in socially disadvantaged schools, principals and assistant principals were asked to write an autobiography. The reflexive value in producing an autobiography prompted leaders to reflect on the unique experiences that had brought them to a leadership position in their current school, and asked them to reflect on how their early lives, family and career had intersected to contribute to their beliefs and understandings about education and educational leadership. Autobiography, as a method of qualitative research, has potential for investigating the ‘fit’ of educational leaders (Tooms & English, 2010). Additionally, auto-ethnography which examines the social and historical production of my own research practice, provides a further critical and reflexive phase (Wilkinson & Eacott, 2013). Employing Bourdieusian methodological thinking tools of habitus, and the mechanisms and conditions of the field, this paper analyses the autobiographies produced of four principals and assistant principals working in some of the most socially disadvantaged areas of Victoria. It examines the utility of using autobiography as a method to investigate the habitus and dispositions of educational leaders in challenging contexts, including their own understanding of their location within the field, and the capitals they bring to their leadership. It evaluates the value of autobiography as a reflexive tool for educational leaders and researchers working in challenging socio-economic contexts.