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This article examines the history and relationship between organizing library workers and creating spaces for critical conversations among those in the field that have occurred in Edmonton since 2010. The reflective piece begins with a short history of the rise of the Edmonton Chapter of the Progressive Librarians Guild (PLG). Despite PLG’s early successes, PLG Edmonton disaffiliated from the broader PLG organization in 2016, and its successor organization, the Information Workers Collective (IWC), ultimately and rapidly failed as an organization. However, an ongoing space for critical conversation was facilitated the emergence of the local Politics of Libraries (PoL) conference largely organized by student volunteers. The article concludes by reflecting on the limits of organizing beyond Edmonton.