In this paper we explore our experiences working with queer and trans youth who have taken "non-traditional pathways out of high school. Drawing on Foucauldian theories of normalisation and Halberstam's queerings of time, success, and failure, we consider how certain aspects of schooling have shaped queer and trans youths' desire to seek out GEDs or early entrance into post-secondary school as strategies to escapes their high school environments. Through our reflection on our experiences with these students, we have identified some of the barriers that these students faced with regard to high school completion. Additionally, we found the tension between success and failure often shaped the alternative paths these queer and trans youth had chosen in an effort to negotiate their schooling experience. In the end, we question the current organisation of secondary schooling and suggest that a (re)envisioning of alternative educational pathways out of secondary schooling would provide destigmatising, non-normative modes of engagement with schools and learning.