In this paper, we look into how country-specific factors shape the interrelationship between childbearing and women’s labor supply. To this end, we compare Italy and Poland, two low-fertility countries where the country-specific obstacles to work and family reconciliation are similarly strong but which differ in the history of women’s labor supply and the extent to which couples’material aspirations are satisfied by men’s earnings. Our findings show that women’s employment clearly conflicts with childbearing in Italy, while in Polandwomen tend to combine the two activities, despite the similar difficulties they face. These results challenged the standard microeconomic explanations and point to the importance of other country-specific factors, apart from conditions for work and family reconciliation, in shaping women’s employment and fertility decisions, such as economic incentives or culturally rooted behavioral patterns. Overall, our study provides thus foundations for explaining the variation in the relationship between women’s employment and fertility in an enlarged Europe.