Recent research in psychology introduces "grit" as a characteristic observable in successful students (Duckworth, 2016). Popular applications of the grit framework can further the notion of "rugged individualism," placing the onus of achievement upon the individual. This perspective can lead failures to be considered the result of deficiencies, overlooking effects of structural factors associated with learning. Sociologically, certain applications of grit can be limited in explaining mobility: they may not address the social contexts of the people they assess; or, they may lack a dynamic understanding of students' cultures. This article applies a qualitative, sociological framework offering "agency" as a concept to complement grit and understand social structures, which facilitate student mobility. Through in-depth interviews, this research gives voice to students who experienced significant upward mobility, despite low-income backgrounds. These cases suggest that interplay between personal agency and a supportive social structure is necessary for students to navigate barriers towards academic and professional success.