With an expansion of global capitalism and global humanitarian crises, a cosmopolitan rhetoric of the shared world community has surged in the past decades. Recent educational agendas emphasize humanitarian and multicultural ideals of cosmopolitanism, and at the same time reflect the capitalist logics to maximize the global mobilities and economic competitiveness of future generations. This thesis investigates how people navigate this vague tension between humanitarian ideals and capitalist impulses. Building on the works of Craig Calhoun (2003) and feminist researchers, this study departs with discussions on the masculine bias behind the universalist and liberal cosmopolitan ideals, and their conceptions of the cosmopolitan self, pertaining to its lack of thick attachments and belonging. I ask: How do young people who are globally oriented and invested in cosmopolitan ideals construct their identities and life trajectories? What dilemmas, tensions, and struggles do they experience when navigating their lives in the global world? I analyze narrative-based interviews with thirteen former students of the International Baccalaureate program and/or United World Colleges as an empirical case of cosmopolitan-oriented individuals. Analyses of the narratives demonstrate a dialectic identity work with value orientations toward equality and diversity, as well as active self-positioning in the global world. An awareness of their own cosmopolitan capital and privileges induces guilt, which demonstrates the tensions between the universalist ideals and the capitalist requirements, as well as a limitation of the liberal frameworks of cosmopolitanism. Real-life struggles and undeniable human attachments and belongings (e.g. financial burdens, longing for home, and physical and emotional fatigue) emerge as embarrassments and obstacles standing in the way of a pursuit of cosmopolitan dreams. An ideal and competent cosmopolitan is thus imagined to be empowered in the particular way that the neo-liberal and masculine subject is, and to only have “thin” and public attachments toward the rest of humanity. The private, personal, and “thicker” belongings and attachments are, though being human necessities, marginalized and excluded as a “hidden abode” (Fraser, 2014) from the imaginary of an ideal cosmopolitan life. This illustrates an empirical dynamic which reinscribes and reproduces the new public and private dichotomy on the global scale.