This qualitative case study explored the perspectives of two high school teachers who approach their work as reflective practitioners, capable of thinking deeply about systemic issues and teachers' work lives. Our research questions included: 1) how do the conditions of schooling influence an intellectual approach to teachers' work?; 2) how do narrowly defined evaluations of educators' work impact teacher morale?; and 3) how do differences in the work of teachers and administrators catalyze division with a school culture? Data illustrate the influence of professional landscapes and unearth how less-than-satisfying conditions are expressed in environments devoid of discourse that fosters an intellectual approach to teachers' work. Findings specifically address solutions and recommendations for supporting teachers through structures for dialogue and action.