This thesis presents the findings of research into how mothers working in the Sixth Form and FE sector experience the family friendly policies in place in their organisations. Mothers of young children are among the largest group leaving the teaching profession each year, citing inflexibility, childcare issues and lack of opportunity in their reasons for leaving and research into this is limited. With a retention crisis in the profession, this thesis offers an insight into how mothers are experiencing the policies designed to mitigate the impact that becoming a mother has on a women’s employment in the sector. Eight mothers working in Sixth Form and FE colleges in the North of England were interviewed about their experiences of pregnancy at work, maternity leave and their return to work following childbirth. Alongside this, the institutional policies relevant to these life experiences (maternity and family leave policies) were analysed. The analysis revealed the difficulties of working motherhood from keeping their pregnancies concealed during the very early days, decisions about the duration of maternity leave and issues arising on returning to work. Participants described supportive colleagues, less supportive institutional practices and a litany of gendered processes and experiences impacting on the way policy was experienced and the work/motherhood choices that they made. Conducted under a novel Matrifocal Critical Realist umbrella and thematically analysed through a gendered organisations theoretical lens, this thesis argues that although the policy makers may have good intentions, the policies are not experienced by any two mothers in the same way. Societal and structural issues have a large role to play in how policy intention is enacted and experienced with the gendered nature of the organisations constraining mothers’ choices and (re)producing inequalities for mothers at work.