This paper reflects on the recounts of a group of 'old boys' about their transition from elite schools to university. Analysis of semi-structured interview data reveals that this transition was not always straightforward. Although educational background has traditionally determined access to, and progress through, university, this paper details the challenges that confronted a group of old boys as they negotiated a landscape that did not align with the positionality they had assumed in their schooling. Defining this as a 'bubble bursting' moment, the participants relay how negotiations of their positionality provoked a reflexive accounting of what to keep and what to reject in the formation of undergraduate identities. The discourses that surround the educational choices made by elite school students indicate how tightly bound notions of achievement and academic excellence define expectations and concomitant senses of Self. Exposure to a larger, and more diverse student population, as well as changed social strata, resulted in the questioning of the elite school environment and the preparation that it provided. This paper explores a currently under-theorised aspect of the literature to detail how the emotions and feelings that elite school alumni experience frames the transition to university.