Schools' structural workplace conditions (e.g. learning resources and professional development policies) and cultural workplace conditions (e.g. school leadership, teachers' collaborative culture) have been found to affect the way teachers learn. It is not so much the objective conditions that support or impede professional learning but the way teachers perceive those workplace conditions that influence teachers' learning. Not much is known, however, about how teachers' perceptions relate to the way they direct their own learning. Using a sense-making approach, we explored how four teachers' perceptions of cultural and structural workplace conditions were related with how they direct their own learning. The four cases were selected from a sample of 31 teachers from two secondary schools, and differed in the extent to which the teachers perceived their workplace as enabling or constraining their learning. We found that the content of teachers' learning goals is related to their perception of shared vision and professional dialogue in their schools, and driven by individual classroom-based concerns. Furthermore, teachers' perceptions of cultural workplace conditions and supportive leadership practices seem to be more important influences for teachers' self-directed learning than their perception of structural conditions.