The transition from primary to secondary school has long been recognised as one of the most challenging in a child's education. Whilst most children ultimately make this transition successfully, it can nevertheless be an anxious time for the majority of children. For a minority, this may lead to high levels of anxiety that can have long-term negative impacts on mental health and wellbeing. Despite a plethora of research on transitions, current interventions are varied and largely ineffective with a lack of focus on the experience through the child's eyes. This paper describes two core themes emerging from an interpretative phenomenological analysis (IPA) study that aimed to uncover the real-life experiences of nine pupils who had recently undergone this transition. Individual semi-structured interviews were conducted at the end of the first year at secondary school. Pupils were asked a series of open-ended questions about their experiences before, during, and after making this transition. Analysis showed that pupils worried about the transition very little whilst in primary school but that anxiety built over the summer break and continued into the start of Year 7. We present only two themes in this paper, (1) the role of Friendships and (2) Family Support, however, additional themes also emerged including Bullying, Teacher Style, Independence and Responsibility, Homework, and Mindset. Possible implications for schools and policy makers are detailed and areas for future research discussed.