College students receive countless messages about "following passion" and "doing what you love" (DWYL). What happens when these repeated messages ultimately do a disservice to some students? Although pursuing one's interests is strongly encouraged, the author explores the limitations of the DWYL advice at all costs, including the privilege that is often tied to Western-oriented career development concepts. Rather than focus solely on passion, career-related discussions with students should include authentic conversations about purpose, meaning, and the shifting future of work--and how students might best prepare for these changes. Several examples of institutional programs are highlighted. Suggestions and implications are provided for higher education professionals and student affairs practitioners.