The Japanese community in Singapore comprises mainly white-collar workers and their families. This article addresses issues concerning education, overseas living, and identity-related investments made visible by way of examining schooling and parenting practices. Framed within a critique which recognizes schooling and identity investment as being inherently ideological in nature, the discussion centers around a Japanese school in whose broader operations both parents and other Japanese institutions are involved. Subsequent analysis is directed towards deconstructing (1) institutionalized practices relating to ways in which Japanese overseas organize their lives and frame their life experiences; and (2) the means by which particular notions of Japanese cultural and national heritage are legitimated and fostered through schooling. The article concludes with the observation that the maintenance of an ideologized form of Japaneseness, and not the engenderment of cosmopolitan or globalized identities, constitutes the dominant driving force behind Japanese-medium schooling in Singapore.