Education is essential to personal welfare. As educational levels increase, personal income rises, the quality of life improves, and society benefits as criminality declines, tax income increases, and the cost of social programs decreases. Unfortunately, every year thousands of students leave high school without graduating. Various factors place students at-risk of dropping out, but the question remains why some at-risk students drop out while others graduate. This phenomenology investigates dropping out by following the philosophy of Jurgen Habermas, guided by the work of Max van Manen. Participants discussed their lifeworld experiences and explained factors that had caused them to leave school. Through conversations with dropouts, this study discovered five themes related to dropping out. These were: In participants' lifeworlds, dropping out was not unusual; participants' worldviews often disconnected from life's realities; participants remained resilient despite their disadvantaged lives and educational setbacks; participants lacked social capital that could have helped them escape their lifeworlds, and participants had often been invisible to people who could have provided help. These themes do not stand alone, but meld into a picture of lives lacking the basic elements of success and the supporting relationships needed to succeed. The study concluded that schools cannot alter many elements dropouts' lifeworlds but can reduce dropping out by identifying potential dropouts and providing supportive personal relationships. This dissertation includes recommendations on how schools can better support disengaged students and recommendations for further research and action to increase graduation rates.