This paper has the dual aim of first presenting an understanding of school dropout as an occupational transition and second, to suggest how this occupational transition may be navigated successfully. School dropout is of concern to occupational therapy as it limits peoples' full social inclusion. We draw on data from a biographical inquiry into the nature of occupational engagement of men in a low socioeconomic, South African community who dropped out of school. In this study, narrative data were generated from 3 men, followed by a narrative analysis and thematic analysis. The findings reflected that two of the men established stable occupational trajectories after dropping out of school, contrasted with the third man who was unable to do this. The interpretations suggest that a successful occupational transition for these two participants occurred through establishing anchoring occupations as a result of chance encounters with individuals who acted as 'champions'. These champions ensured the successful negotiation of available opportunities. Through offering these insights, this paper provides an illustration of how concepts interpreted and discussed in occupational science, such as occupational transitions, have relevance to occupational therapy. With regards to the occupational transition of dropping out of school, it is recommended that occupational therapists consider how they might promote access to champions of opportunities that lead to the development of anchoring occupations.