In the contemporary work landscape, individual workers increasingly create, sustain, and manage their own careers. Business schools prepare students to enter careers using a vocational approach that neglects the cultural lens on why students desire the careers they do and how they perceive those careers over time. In this essay, we argue that career education entails not only assessing and developing individual strengths and skills but also pondering the context, purpose, and scope of one's career. Our proposed pedagogy is: (a) interdisciplinary, blending insights from management and the humanities; (b) centered in narrative, specifically film narrative, which forms the central organizing principle of the course; and (c) historical, analyzing the narrative themes and subtexts that recur over time. We seek to move beyond a "how-to" approach, focusing on skills students need to succeed in their initial jobs, toward a "why do?" interrogation of the cultural and historical roots of work and career attitudes. This approach challenges students to critically examine ideas about what makes a good career--for themselves and others--over the long arc of their working lives. We present some key tenets of our proposed approach, using examples and evidence from a class we co-taught to illustrate them.