As middle grades teacher educators, we carry a responsibility to prepare pre-service teachers for the realities of practice ahead in their real-world classrooms. Similarly, middle school instructional coaches and specialists support in-service practitioners within the authentic context of their real world, real time experiences as teachers. In the roles of middle grades teacher educator and middle grades instructional coach, there can be a considerable focus on theories that underlie best practices, but what happens when theory and practice have untested connections or when theory and practice diverge? And, what happens if teacher education fails to focus on maintaining an authentic context in the real world? In "The Successful Middle School, This We Believe," Bishop and Harrison put forth the importance of ensuring clear correlations between theory and practice, as the idea that professional learning for all staff [should be] relevant, long term, and job embedded. Within this descriptor of doing middle school successfully is a call to continuously examine connections and disconnections between classroom theory put forth by teacher educators and authentic, current middle grades practices. This article tells the story of a collective self-study between middle grades teacher educators who were seeking to interrogate connections and disconnections between theory and practice. In shared inquiry and critical reflection, we sought, not only to uncover problems of practice in our professional spheres, but also to confront the gaps that emerged between theory and practice, looking for ways to more explicitly connect our work with the middle grades In Real Life (IRL).