Departing from an understanding of today’s liberal capitalist society as deeply concerned with individual growth through higher education, this paper aims to explain the well documented fact that working class students are underrepresented within the higher levels of the Swedish educational system. The study assumes that the prevailing recruitment pattern is created by informal societal structures influencing the individual decisions of would-be students. It then continues to explore the decision-making processes leading a number of students from working class backgrounds into higher education, as well as their experiences of navigating this new environment, in order to better understand the obstacles that this group need to overcome in order to enter the academic area. This is done through an analysis of semi- structured interviews, informed by the career choice theory of Careership. The reading shows that these student’s choice to enter higher education largely has been a pragmatic-rational one, driven more by the need to adapt to circumstances like a changing job market than social expectations to continue their education. The interviewed students often describe the process of entering this new arena as filled with feelings of inferiority and a sense of not belonging that seems to persist even after they acquire additional cultural capital in the form of knowledge and acceptable behaviors. The results of this study implies that a long-term approach towards reversing recruitment bias within higher education must start with the development of a full understanding of these and other challenges facing underrepresented groups.