In this article, I reflect on the negotiations involved in childcare arrangements during the first year of life in two groups of mothers in Santiago. I focus on the ways in which local imageries of motherhood interact with global tendencies in intensive mothering and the current public encouragement of increasing women’s participation in the workforce. In this study, low-income and lower middle class women prioritize staying with the baby over the year, becoming the main caregiver, and opting for giving up work and other relationships. In contrast, middle-class women go back to work by month six and combine different childcare alternatives. I argue that these women embody two ways of being a mother following different kinship expectations, relationship with expert trends, and cosmological aspects of motherhood. Consequently, they follow different paths in childcare decision making and in the management of concomitant emerging feelings such as guilt.