The purpose of this study was to examine compulsory schooling in the United States and its potential to provide an inconsistent avenue to employment for students from neighborhoods of differing socioeconomic status. Specifically, this study asked why do students from privileged neighborhoods typically end up in positions of ownership and management while those from impoverished urban or rural neighborhoods end up in working-class positions or involved in cycles of incarceration and poverty? This research involved the use of qualitative methods, including participant observation and interview, as well as photography, to take a look at a reputable private day school in the southwest. Data was collected over the span of eight weeks and was then analyzed and compared with preexisting data on the schooling experience of students from impoverished urban and rural neighborhoods, particularly data focused on juvenile detention centers. Results showed that compulsory schooling differs in ways that contribute to the preexisting hierarchical class structure. The research suggests that schooling can be detrimental to the future quality of life for students in impoverished neighborhoods, which questions a compulsory school system that exists within the current hierarchical class system.