It has been argued that middle-class parents engage in the ‘concerted cultivation’ of their children with a view to securing their future status. One aspect of this ‘concerted cultivation’ entails the enrolment of children in organised enrichment activities. While scholars have focused on the ‘enrichment’ market for school-aged children, few have examined the preschool market. This article presents an analysis of a Sydney-based Australian parenting publication with a focus on advertisements for enrichment and entertainment activities targeting preschool-aged children. Many of these advertisements promote the message that future educational success is predicated on parental investment in the preschool years and mothers/parents are urged to do all they can to give their child a ‘head start’ on learning. This analysis highlights how these activities are promoted as a strategy for class reproduction, suggesting that anxiety about children’s future status has seeped into the preschool years.