In today’s higher educational context, an increased focus on accountability and impact factors brings with it a greater expectation for academics to publish. Within the scholarship of teaching and learning, academic writing is a complex act that requires attention. Academics with strong expectations to be productive may nonetheless experience the writing process as isolating, lonely or overwhelming. In this chapter, we examine models and structures that foster a culture of academic writing within a post-secondary context. We then describe the evolution of our writing group’s community of practice approach – one in which academics engaged in various forms of writing spanning the spectrum from reporting for academic and scholarly journals to writing for the general public and social media. Drawing from Schön’s (1983) reflection-in-action and reflection-on-action model, we illustrate through current members’ experiences and insights how the writing group has – and is – impacting their writing and professional growth as academics. Through the analysis of our narratives, we identified factors that influenced the success of several cycles of our writing group, as well as the conditions required to support both individuals and the collective. Recommendations for writing group practices emerge from our findings.