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In this paper, the author contends that if the outsider-researcher involved in Information and Communication Technology for Development really wants to make a difference and honestly address the emancipatory interests of the developing community, social transformation will have to occur on both sides of the “development divide.” This statement implies both an understanding of the researcher’s own ethnocentrism, prejudice, assumptions and inabilities as well as local concerns, needs, expectations and realities. Using critical social theory as a position of inquiry and learning from the enculturation phases of critical ethnographic fieldwork in a deep rural part of South Africa, the paper presents three confessional narratives where the author reflects on how he confronted his own need for emancipation. Research results include lessons learned on building networks of friendships, traditional leadership and respect and the typical people-orientatedness of deep rural South African communities.