When Ontario eliminated its unique fifth year of secondary school for post-secondary bound students, policy makers, educators, and the general public anticipated that the province would finally adhere to the four-year model of secondary education common to the rest of English speaking North America. For a significant number of students, however, this outcome did not prove to be the case; a substantial proportion of adolescents, having met their graduation requirements, voluntarily chose to return to their former schools for an additional semester or two of secondary education, a phenomenon referred to as the “victory lap”. Utilizing a mixed-methods approach, this study was conducted among first-year students Concurrent Education students in a small Ontario university and examined some of the factors that motivated students to opt for either the direct entry or “victory lap” pathway to university. Results suggest that the “victory lap”, while being a predominately male phenomena, may be a form of transition anxiety.