This paper presents the findings of a self-study exploring the experiences of women leaders, and the intersections of leadership work with roles as mothers. Drawing on narratives of women from across experiences of leading to support women in the workplace, to women who juggle leadership work and mothering, and women whose mothering involves caring for children with Special Educational Needs and Disabilities, we address the dearth in scholarship addressing these positionings and implications for women in leadership. Using self-study as a qualitative approach to bring together three current school leaders and an ex-principal, this study uses autobiographical experiences and shared reflections on blogs and materials accessed through our professional networks to contribute robust and rich analysis of personal narratives on the challenges and opportunities afforded to women in the state school context in England. We apply a conceptual framework of micro-meso barriers to consider the relationship between self and organisation level interactions. Findings contribute strategies from the personal to the organisational, with implications for the ways in which coaching, flexible working and an equitable approach to decision making can be utilised by schools to support and engage women without a sense of compromised leadership practice or motherhood priorities.