This paper explores women’s changing roles in paid work and the family as Estonia makes the transition from Soviet-style socialism to western capitalism and prepares to join the European Union. It charts linkages between women’s employment and their efforts to combine work and family life as an emerging area of public policy concern in Estonia. The paper argues that the reconciliation of work and family life is not yet a very ‘live’ practice in Estonia. Until recently, a few good quality surveys had been conducted, but no policy impact assessments. The paper provides an overview of the main trends in the options available to women as well as the penalties they have paid as parents in the labour market during the transition of post-socialist Estonia. It considers the main findings from social science surveys and discusses the reasons for the relative shortage of public policy measures and the unwillingness on the employers’ side to address the work-home balance issue more actively. More comprehensive research on workplace practices is advocated as well as a needs assessment analysis to provide a better understanding of the interplay between employment patterns and family-related conditions.