Education is commonly lauded as a guarantor of a social contract in which citizens accept state authority in exchange for conditions for citizens to thrive and achieve social mobility. In the past two decades, the aim of educating for the “knowledge economy” has grown prominent in development discourses and is championed by an array of actors, including national governments, donor agencies, and private philanthropists. Since 2003, Jordan has partnered with organizations to enact educational reforms to realize this vision of progress. These efforts have been accompanied by a series of top-down campaigns in Jordan aimed at fostering national unity and youth participation in public life. These attempts to produce empowered and educated national subjects, along with Jordan’s relatively high rankings on development indices, have contributed to its image of stability and moderation in an oft-volatile region. Yet high rates of youth unemployment and political marginalization in Jordan, along with regional conflicts fueling the displacement of hundreds of thousands of refugees, challenge this image and other assumptions about political authority, socioeconomic mobility, and purpose of education. This paper presents emergent findings from an ongoing longitudinal qualitative study of eight Jordanian university students. Drawing on data from an ethnographic case study of two government high schools for boys in 2007-2008, along with annual interviews conducted with a subset of original and new participants since Summer 2014, this paper endeavors to map how the pursuit of education has become a process fraught with ambivalence amid larger conditions of social uncertainty. Additionally, the paper explores the following questions: How are the aspirations of a livable life mediated through interactions with educational institutions, and what do those interactions tell us about possibilities for youth belonging in these times?