Two university professors and 11 urban school faculty collaborated on a professional development (PD) effort focused on critical literacy to explore literacy practices aimed to reshape definitions of literacy that involved questioning power relationships concerning the environment and social justice. We examined the journey of a veteran teacher, Jan. We found that 1) small, carefully planned PD, considering the specific context of the school, "did" influence her practices toward leading critical conversations concerning the environment and social justice, and 2) that she juxtaposed teaching practices and concepts of critical literacy with school and district initiatives having different theoretical frames.