Understanding why headteachers leave their posts and leave headship before retirement is crucial to limit the haemorrhaging of headteachers from the system. We utilise the communities of practice framework to examine the identity work of Anglican headteachers as members of multiple communities. The challenges of negotiating meaning can lead to dis-identification with members and/or the practice of communities and is made more complex by the need to reconcile different forms of membership across boundaries. This conceptual framework provides a powerful analytic tool through which to understand the identity work of headteachers and headteacher departure.