To explore the ways context may shape career choices, we used a qualitative approach to analyze interviews with college-oriented high school students from the rural Central Appalachia region of Virginia. Using social cognitive career theory, we analyzed pathways to career choices and relevant contextual factors, using data from 24 interviews. Results revealed that participants' pathways partially matched the model, though we also found variant pathways triggered by significant environmental influences and incomplete pathways due to variations in possible career plans. Explanatory factors included status as prospective first-generation college student, outcome expectations that included remaining local and having job stability, and an emergent factor of continuing generation Appalachian. The patterns that emerged with respect to contextual factors and career choice pathways highlight the importance of culture and context when examining how students make career choices. This research extends prior research by examining career pathways using student's own words as data. Moreover, the patterns offer insights career coaches, counselors, and educators can use in supporting students' post--high school career planning.