This study examines a two-year effort to engage groups of inner-city students in community engagement projects at Social Action Charter High School, SACHS, in Milwaukee, Wisconsin. In this project, graduate student volunteers coached small groups of students working on community change projects, collecting data on what happened over time. Kahne and Westheimer (2006) identified a key challenge to projects of this kind. On the one hand, social action projects seem able to enhance students' belief in their own capacity to solve community problems only if adult allies make sure the students do not encounter any significant barriers to success, although this misleads them, albeit unintentionally, about the realities of unequal power in society. On the other hand, authentic engagements with real-world institutional power tend to reduce students' confidence and their desire to participate in social action in the future. Thus the "catch-22" in our article's title. This article shows how one of the groups we worked with at SACH discovered a middle way between Kahne's and Westheimer's two extremes. Even though the students were not able to overcome the power they encountered, they nonetheless found creative and pragmatic ways to accomplish significant tasks. We argue that the students' experience shows a possible avenue for educators to move beyond the catch-22. (Contains 1 table.)