Starting high school can be a challenging but also exciting time for students. The focus of this paper lies with students’ experiences of transition into secondary school. Sixteen students from one government school in New South Wales kept a journal for their first ten weeks in high school as a way of recording their experiences. Their journal entries were studied utilising a phenomenological psychological approach following Giorgi (1985a, 1985b). The aim of this research approach is to produce clear and accurate descriptions of a particular aspect of human experience (Polkinghorne, 1989) in order to reveal the essential structure of the phenomenon under investigation. Emerging from the study were seven themes about transition: the pivotal role of peers in helping or hindering settling into high school; the place of school support through programs and activities; the challenges of new procedures; different types of learning activities; feelings of confidence and success that can enhance transitional experiences; the place of homework in the academic curriculum; and the role of teachers in affecting student integration into high school. The paper concludes by raising some important issues and implications for school based practitioners.