Childhood statelessness is an urgent global human rights issue. Yet, there is limited ethnographic data on the everyday and varied experiences of stateless children and youth, whose representations in mainstream media and campaign materials tend to transmute them into generalized subjects with an ostensibly universal experience of total abjection. Drawing on thirteen months of ethnographic fieldwork in northern Thailand, this chapter examines the process of ‘learning to be stateless’ among Shan youth participants and the impact of statelessness during their various life stages. The chapter argues that statelessness is not necessarily a fully and actively internalized status since birth but a dynamic condition that constantly undergoes re-interpretation by the affected youth at punctuated moments and at various life stages. By examining the contemporary regime of statelessness in a country such as Thailand, where stateless persons have access to certain rights as children but not as adults, this chapter calls attention to the intersection of life stages and statelessness and the complex ways in which such regimes of simultaneous inclusion and exclusion place the emotional and practical burdens on stateless persons as they transition from childhood into adolescence and adulthood.