The purpose of this collective case study is to describe the lived experiences of three secondary educators assuming the dual roles of teaching in a core content area and coaching an athletic team during their first semester of employment. Through the lens of occupational socialization, this study explores the significance of previous life experiences on teaching/coaching orientations, the perceptions and motivations of core content area teacher-coaches, the relationship between the social positions of teaching and coaching, and the effects of teacher-coaches' daily experiences on identity formation. Utilizing various qualitative measures such as observations, interviews, and artifacts as well as a series of open, axial, and selective coding during data analysis, this exploration into two of the most recognizable roles in secondary education is intended to shed light on the phenomenon of what it means to be a core content area teacher/athletic coach in the twenty-first century. Six central themes have emerged based on the cross-case analysis of the socialization of the three primary participants in this study: (1) opportunity, (2) inductive experiences, (3) balance, (4) mentality, (5) connecting social positions, and (6) disposition. Findings suggest that while athletic coaching and numerous other responsibilities can lead to interrole conflict, the social positions of teaching and coaching may also serve to complement one another in a more symbiotic relationship. Based on these findings, implications for teacher education programs, nontraditional alternative certification programs, coaching education programs, and academic and athletic programs in secondary schools will be discussed.