This reflective essay investigates why writer's block affects novice and expert writers on a continuum from students in first-year writing seminars to teachers of writing, paying particular attention to the shared experiences of this pair of practitioners. I begin by focusing on my own experiences as a blocked writer making a disciplinary shift from literary to writing studies after receiving my doctorate in comparative literature from the University of Chicago. By setting a literature review of writer's block against a close-reading of a student case of writer's block in a first-year writing seminar, I illuminate how the difficulties of becoming an expert writer are shared by beginners and professionals as they are socialized into new disciplines. Through our students' work, we can see the complex disciplinary and rhetorical practices needed to enact scholarly moves, and we can better empathize with their and our own struggles with writing, particularly when we begin new projects or cross over into unfamiliar disciplinary terrain.