The stories that people tell about their lives in the context of educational relationships draw attention to the possible experiences through which their lives could grow in meaning. In this collaborative reconstruction of one person’s life history, I present an interpretive retelling of several life stories that this person—Gurraacha Sabaa, an Oromo activist—told me as part of my work at the Dream Desk, a community-based education project designed to strengthen and support learning networks in the communities around a public library in Minneapolis. My interpretive retelling of Gurraacha’s life stories is based on the search for educational possibilities that organizes my work at the Dream Desk. This work requires a broad understanding of education. Thus, I define education as the process by which meaning grows in human lives. This broad definition of education is directly inspired by the work of philosopher John Dewey (1916). It is a way of translating a technical definition of education given by Dewey into the more practical terms required for my work at the Dream Desk. According to Dewey, education is a “reconstruction or reorganization of experience which adds to the meaning of experience, and which increases ability to direct the course of subsequent experience” (p. 82). In Dewey’s definition, the process by which meaning is added to experience is a process of growth. Further inspiration for this broad definition of education is drawn from the work of historian Lawrence Cremin (1976) and anthropologist Hervé Varenne (2007), both of whom recognize education as a fundamental human experience that is not limited to what takes place in schools. By attending to the life stories of one person, I explore the educational possibilities in his life as well as the particular conditions that restrict the realization of those possibilities. Our search for educational possibilities focuses on potential educational experiences related to Gurraacha’s interest in human rights advocacy. And our collaborative reconstruction of his life history focuses on the ways in which the meaning of human rights advocacy is growing in his life. While interpreting the trajectories of meaning revealed by his life stories, I also interpret the educational possibilities created by the ways in which his life history is collaboratively reconstructed in our educational relationship. These interpretations include attention to the practical guidance his life stories provide for our work together as well as the way in which they address me at a symbolic level, marking the differences between my experiences as a white American man and his experiences as an Oromo man. As Jackson (2002) describes, storytelling is both a strategy for “transforming private into public meanings” and a strategy for “sustaining a sense of agency in the face of disempowering circumstances” (p. 15). That is, life stories do much more than provide life with coherence and order (Linde, 1993; Ochs & Capps, 2001). Life stories have democratic and existential imperatives. These democratic and existential imperatives shape the intersubjective space created in the dialogue between my perspective and Gurraacha’s perspective, which is the basis for our educational relationship and our search for educational possibilities. In conclusion, I propose collaboratively reconstructed life histories as the foundation for an ethnography of educational possibilities, a form of social inquiry that not only supports educational action but also is shaped by its exigencies.