This thesis is an exploration of the dialectical orientation of two worker cooperatives in Canada: Mondragon Coffeehouse in Winnipeg and The Sleepless Goat in Kingston. It explores the contradictions these two organizations must navigate within a pro-bureaucratic capitalist environment and how these contradictions have contributed to their development and, more specifically the development of the individual members. The analysis is based on the key theoretical concepts of worker cooperatives, democratic-collectivist organizations, revolutionary praxis, and solidarity. Beginning from the experience of individual cooperative members, this thesis makes the connection between the alternative organizations structural development and the self-changing of the individual. This reinforced Karl Marxs notion of revolutionary praxis which suggests a correlation between the changing of circumstances and individual change. Based on a comparative analysis between two worker cooperatives, using twelve in-depth, semi-structured interviews the research revealed a number of key findings. The main finding was that despite beginning with similar structure and intent over a decade or so these two organizations developed in largely different directions. While Mondragon was able to maintain its political commitments and democratic-collectivist structure, The Sleepless Goat became more concerned with business practice and in the process allowed its political commitments and collectivist structure to fade. It was found that cross-movement solidarity, recruitment practice, and effective communication of goals and practices were all contributing factors in the maintenance or erosion of social movement goals.