This chapter analyzes young people’s pursuit of their personal aspirations against China’s and Taiwan’s economic and political domains. Discontent and frustration with one’s personal life are often closely tied to political events and economic changes and their perceived impact on individual opportunities. This chapter offers an excursion into how the economic and political trajectories of China and Taiwan have influenced the hopes and aspirations of individuals differently across the generations. Specifically, I will explore how important historical events in these two societies have left their imprint on the personal family histories of my interlocutors and thus shaped their sense of national identity and belonging.