Social and cultural geographers have developed an important body of work on men, masculinities, and masculine spaces (e.g., van Hoven and Hörschelmann, 2005; Gorman-Murray and Hopkins 2016). Informed by feminist scholarship and critical men’s studies, this work has examined masculinities as provisional, place-based performances, situated within a broader field of structured gender relations. In this paper, I contribute to this body of work through an analysis of performances of masculinity within the space of post-secondary education.  Drawing upon interviews with a small but diverse sample of participants, I examine the ways in which young-adult men draw upon, adapt and challenge masculine norms as they transition from high school to university, and as they plan for future careers.  Connecting early life histories, academic experiences and career aspirations with participants’ understandings of gender norms, the research illustrates how men engage in varied performances of masculinity in the context of educational spaces.  My analysis demonstrate while some men have an understanding or clear image of their career trajectory, many express anxiety about futures.  This anxiety reflects the increasing uncertainty of securing ‘good jobs’ in the current labour market set against the enduring norm of the male breadwinner.  While many participants see a university degree as a necessary credential for labour market success, their degree and course choices signal a diverse range of masculine performances in the context of post-secondary education.  This, in turn, informs different views on what it means to do masculinity in the current context.