Women in contemporary western economies have both more options and more pressures to combine work with family responsibilities in the early years of motherhood. This chapter examines how these options are exercised as women make decisions about re-entry to the workforce following the birth of their first child. We present an analysis of data from a cohort of Australian women, tracked longitudinally from pregnancy until their first child was 18 months old, to identify patterns of approach and salient factors of influence as they negotiate the dual challenges of re-entry to the workforce and finding acceptable childcare. Mothers’ work intentions were mapped against actual return behaviour with return assessed at 6, 12 and 18 months after birth of their child. Early returns were associated with jobs that offered less provision for maternity leave and availability of familiar trustworthy childcare. All mothers had high satisfaction levels with motherhood and their mothering role. However, working and non-working mothers rated the costs and benefits of maternal employment differently. Working mothers were more likely to see maternal employment as increasingly beneficial and less costly across the first 18 months of their child’s life. Each generation of parents face different challenges in finding the balance between work and care. In this contemporary sample of mothers, the majority returned to work and adapted to the new reality of work options, which were somewhat different from their pre-parenthood ideals.