The authors used qualitative case study methodology to explore parents' perceptions of their children's readiness for kindergarten. The authors interviewed parents, focusing on their children's experiences during their transition from a child-centered, play-based preschool setting guided by an emergent curriculum into a range of diverse kindergarten environments. Using data from parent interviews at the end of the children's kindergarten year and from the children's formative preschool assessments ("developmental stories"), the authors focused on six children's experiences of transition to kindergarten. Findings suggest that habits of mind developed during the preschool experience figured prominently in the children's transition processes into a variety of kindergarten settings, enabling them to successfully navigate their new, more structured environments.