Mitchell (2008) asks faculty to adopt “a ‘critical’ approach to community service learning” (p. 50), one that focuses on social change, redistribution of power, and the development of authentic relationships. However, the path of transformation from traditional to critical service-learning practices remains unexplored. In this autoethnographic reflective essay, five individuals share their journey from higher education institutions as they engaged in a community of practice examining their own questions, assumptions, experiences, and positionality to more fully understand critical service-learning (CSL). This essay documents self-discovery through an iterative reflection process, detailing the approach used to examine CSL and interrogate the relationship between positionality and critical theory. This process provides a roadmap for service-learning practitioners interested in developing their own critical consciousness. Key outcomes include a conceptual model positioning CSL on a spectrum, in which one may approach without necessarily achieving social change, and the development of a toolkit of CSL resources.