This article considers how technical communication practitioners and teachers can approach Donald Schön’s notion of problem setting as rhetorical and reflective work that offers us a richer, more precise language for articulating the technologies, narratives, and values from which problems appear as problems in the first place. The author posits that problem setting, when foregrounded in our work, adds value to the knowledge we make in practice rather than the knowledge we gain from stepping back and abstracting. After briefly describing problem setting as a significant yet invisible practice already underlying technical communication, he then describes a vignette from a digital marketing and design firm to foreground problem setting as creative, on-the-spot reflective work that we often use to invent, rather than discern, problems in unstable situations. The larger goal of this article is to further investigate Schön’s past construction in order to examine how the practice of problem setting affects our ability to act within the instability of digital, divergent, and knowledge-intensive settings—the kinds of settings we regularly face in the workplace and the classroom.