This article argues that the primary role of the instructor is to help students understand and work with the difficult emotional states that arise from struggling to learn. Drawing on Sianne Ngai’s theorization of “ugly feelings” and using his own experience with digital humanities instruction as a case study, the author offers ways to center emotional work, especially work involving frustration and anxiety, in the classroom. Asking students to develop failed prototypes and reflect on the process, for example, can provide them with a better sense of what it might mean to succeed. Giving the same exercise twice, with artificially imposed difficulties the second time, might help them learn concrete steps for working through mounting irritation. In short, frustration and anxiety are not things that emerge from time to time—they are ever-present. The author argues that it is the job of instructors to develop ways to prepare students not for the unexpected failure but for the inevitable frustration that comes even with success.