In this paper the authors reflect on the experience of a head of school's learning process while assuming his teaching and leadership role. This reflection is guided by Jack Mezirow's (1978) ten phases process of transformative learning and a reflection on Albert Camus's fictional story The Guest. The paper uses Mezirow (1978) ten phases process as a hermeneutic tool to interpret the transformative learning operations (how) of teachers. The data generated from interviews focuses on the personal and professional transformation of a Maltese head of school who together with the school teaching community underwent, partly as a result of participation in a professional learning program, a programme that led to a transformative experience. During this professional development teachers were introduced to the Let Me Learn (LML) learning Process, a process that seeks to assist teachers in learning about themselves as learners and their students. The LML process seeks to create a community of learners that engages with the different learning processes of each member of the learning community including the teachers themselves.