Dewey argued long ago that to learn something one has to undergo some experience. In a classroom, teachers have a range of tools to engage, entice, or threaten students to engage in activities that are designed, in one way or another, as experiences that will lead them to learn something. In schools, teachers have institutional power and grades to (at least try to) compel students to participate in these experiences, however fully, whether they want to or not, or whether they really understand why they are engaging in them. Of course, this is not what Dewey championed--he wanted students to engage with activities that they were motivated to do themselves, intrinsically. This essay uses the case of community-based education, like community organizing, to explore the tensions and contradictions one can encounter when one cannot mandate that people engage in a learning experience. The point is not necessarily that Dewey directly informed organizing, but that a juxtaposition of these two related stances is illuminating for educators. The author expands the discussion beyond experiences in general to talk about what L.A. Paul has called "transformative experiences," complicating the challenges involved in the relationship between motivation and experience even more. Ultimately, this paper argues that there is a long history of educational approaches (including Dewey's) that leverage student motivations for engaging in activities to learn things that the students themselves were not necessarily aiming for. In other words, getting students to do the "right things" for the "wrong reasons" is a long-established educational strategy. In fact, this article explores the possibility that, it may not actually be possible to engage students in "transformative experiences" in particular, perhaps the most effective "educational" experiences for the "right reasons."