In an attempt to transform a skills-based graduate course into a theory-driven multimedia storytelling course, a first-year assistant professor encounters diverse obstacles that upend their initial pedagogical intentions. This evocative autoethnography explores the course instructor's experiences as they deal with issues of decreasing student engagement, complex class dynamics, and growing institutional pressures. As the semester advances and the course becomes completely and forcefully transformed, several attempts are made to preserve key aspects of the original plan, despite the multiple failures encountered along the way. Reflecting on the problems evidenced throughout the entire semester, the instructor re-evaluates the pedagogical value of their approach, vis-à-vis the uncertainty and frustration encountered by their students.