Effective elementary principals enact "leadership for literacy" to support high quality literacy instruction. Yet not all elementary principals possess strong literacy knowledge. This study examines how principals with different professional backgrounds learn about and enact leadership for literacy and how the embedded systems of principals' work impact literacy leadership. We use interview, survey, and observation data to identify five learning trajectories for elementary principals. Across the trajectories, principals enact leadership for literacy differently depending on their level of literacy expertise. Principals with less expertise compensate by working with teacher leaders or fellow principals, acquiring more expertise, or emulating other principals.