A disorienting dilemma is a catalyst for change in perspective that may culminate in transformative learning. The authors analyze three activities in higher education that created disorienting dilemmas--a field trip, a service-learning experience, and study abroad. Results indicate that a disorienting dilemma can prompt students and faculty to reflect on assumptions about self and society, leading to deeper self-understanding and increased awareness of faulty assumptions reinforced by one's culture. Reflection and discussion are necessary to develop skills for managing change and, ultimately, to take responsibility for making sense of experience. The process of change is unique to each individual. Educators can assist students in navigating changes in perspective by incorporating strategies that encourage them to think more deeply about and draw from experience. Reflecting on their own learning can enhance educators' ability to foster change in their students. Mezirow's (1978, 1991, 2000) theory of perspective transformation offers a model for understanding and implementing the process of change.