The space between project goals and project outcomes is a rich location for reflection and learning. This article explores that space in relation to Adventure Territory, a youth theatre performance project that involved residencies at two secondary schools in the remote Northern Territory town of Katherine. The 12-month project was facilitated by Australian Theatre for Young People, a Sydney-based youth theatre company located some 3,600 kilometers away from Katherine. This article describes the action evaluation of that project and provides an analysis of what was learned when delivering this “fly-in, fly-out” (FIFO) project. The evaluation demonstrates that although there were positive outcomes for some young people, the project did not go according to plan and many goals were not achieved or became irrelevant. The reasons for these varied outcomes are explored, and we propose that future FIFO projects would benefit from adopting a community cultural development approach to youth theatre work. Such an approach demands that we take time to understand the context, build relationships and participation, and develop goals with, not for, the communities with which we work.