How might teachers transform routine tasks into non-routine ones? The purpose of this article is to address this question. The article opens with a discussion of why non-routine problems require creative and original thought. Specifically, I discuss how non-routine problems require students to confront uncertainty and how uncertainty can serve as a catalyst for creative thought and action. Next, I discuss how the logic of routine tasks can impede original and creative thought. I then introduce the concept of lesson unplanning and explain how it can be used to convert routine tasks into non-routine problems. I also discuss how non-routine problems can range from more modest in-classroom assignments to more ambitious efforts. The paper closes with a brief discussion of directions for future research and practice.