This article examines the formation of flexible citizens embodied by Japanese Filipinos who were born in the 1980s and 1990s. Using flexible citizenship (Ong, 1999) as the analytical tool, the author explores the lived experiences of Japanese Filipinos through their experiences of flexible mobility, individual freedom and self-enterprising within the contexts of migration policies, nationality laws, family values and the job market. Based on an ethnographic study, this paper suggests that the flexibility of middle-class and educated1 Japanese Filipinos is embedded in the new possibilities and constraints created by the institutional structures of the Philippine and Japanese governments. They do not simply acquire the legal status to an imagined, developed Japan for higher social mobility, but rather their experiences are complex ways of acquiring legal status in one nation-state without completely cutting ties with another, while maintaining family and social group cultural values and accumulating different forms of skills within their constructed transnational arenas. This is the basis by which they then propel themselves into becoming employable in a globally competitive job market. Another form of mobility, in this case from Japan to the Philippines, is used by parents to impose disciplinary actions upon Japanese Filipinos. Flexible citizenship is thus a form of mobility for complex, sometimes contradicting, reasons constructed, negotiated and/or contested by Japanese Filipinos while continually transforming their subjectivity in the contemporary transnational context.