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. This paper results from our joint concern about the normative expectations of success and failure surrounding students' transitions out of secondary schooling. In our experience working with queer 1 and trans 2 youth, we observed youth's struggle with this transition in ways that seemed to indicate that their presence alone put a wrench in the system. That is, their queer-ed and trans-ed bodies did not fit into the predetermined tropes of 'successful' high school student, high school graduate, college-bound student, or, even, high-school dropout. Normative conceptions of the pathways out of and away from high school are discursively produced by systems of power that keep notions of youth and success static and serve to discipline educational thought (Foucault 1977(Foucault , 1978. Our project, then, is to interrupt the processes leading to the labelling of students' and their educational paths as either successful or failing while simultaneously troubling the construction of these two positions as binaried. We centre this paper on the following question: what possibilities might a queering 3 of the discourses surrounding success and failure in school mean for discussions about education today? Given our research interests in queer and trans youth who have navigated out of secondary school settings in 'non-traditional' ways, we intend to examine what these normative educational discourses do to students who commonly get labelled as failures.In this paper, we examine our experiences with and understandings of how queer-and trans-identified students negotiate dominant educational discourses in relation to the barriers they faced while making the transition out of high school. We argue that a reconfiguration of the stigmas associated with high school incompletion and/or non-traditional pathways to college and university need to be (re)considered as being implicitly tied into the normative discourses of secondary schooling and the expectation that all students follow...