This chapter elucidates how the specific demographics of China and Taiwan have given rise to different education systems that resulted in diverging degrees of independence from parents. Providing insights into young adults’ memories of their early educational careers, this chapter outlines how the schooling systems in China and Taiwan in the late 1980s and 1990s wore the imprint of very different state ideologies that had a decisive impact on how children and teenager perceived their vocational and academic opportunities. Moreover, it will be shown how parental ambitions as well as early experiences of success and failure in schools affected aspirations and perceptions of personal agency differently among my young Chinese and Taiwanese interlocutors.