This article examines the contested transformation of parenting discourses in postwar Taiwan as a case of global sociology. The author argues that such transformative change embodies Taiwan’s compressed condition of modernity, entangled with a variety of global forces and transnational connections. This article looks at two critical periods of discursive transformation, including a top-down project marked by US aid and the family planning programme during the 1950s and 1960s, and a bottom-up campaign activated by transnational elites to advocate schooling reform and parental education in the post-Martial Law period. The author raises the concept ‘glocal entanglement’ to describe the cultural and institutional entanglements between societies under asymmetrical power relations, and emphasizes that parents across class divides had differential access to globalization and uneven relations with the modernity projects.