Research examining middle‐class parents' school choices often overlooks parents in post‐socialist nations, where social reproduction may occur differently than in Western urban contexts. To bridge this gap, our study illuminates the intersection of Czech middle‐class parents' school choices and parenting strategies. Drawing on 26 in‐depth interviews with parents, we depict “cultivation for wellbeing” as a distinct parenting approach prevalent within a subset of the Czech middle class that challenges prevailing Western depictions of middle‐class child‐rearing strategies in relation to school choice. We describe five areas in which the parenting approach contrasts with concerted cultivation and intensive parenting: the promotion of unstructured free time, autonomous socialization with selected peers, a propensity to avoid confronting teachers, gentle support for children's interests, and a focus on emotional and physical wellbeing. We posit that “cultivation for wellbeing” serves as a mechanism for social distinction among a segment of middle‐class parents, enabling them to distinguish themselves from other class segments by selecting and seamlessly accessing exclusive public school settings tailored to their nuanced educational preferences. The study underscores the need to reassess the dominant portrayals of middle‐class parenting strategies, highlighting the complex interplay between child‐rearing, school choice, and social reproduction in diverse cultural contexts.