Classroom as organization (CAO) is an approach at the extreme end of an experiential learning intensity continuum. While proponents suggest they would never go back to a teacher-centered classroom, CAO has not become widely adopted since its initial description by Cohen. We argue this is, in part, because of shadow elements that may discourage faculty in both initial adoption and persistence in the journey from novice to master. This article reports the authors' reflexive process related to the shadow elements they encountered as early adopters of the CAO methodology. The article begins with a brief background on CAO, followed by a discussion of shadow elements that manifest at the student and faculty levels. We include our recommendations for practice.