The gradual commodification of higher education in the context of an increased focus on graduate employability attributes together with evolving labour markets is creating challenges for universities and students alike. For universities, there has been significant investment in careers services and, through institution-wide initiatives, employability or graduate attribute development established to support graduate transitions into work. Meanwhile, for students, experience of part-time work together with pessimistic post-recession employment discourses are challenging the notion that a good degree guarantees their future career prospects. Simultaneously, decreasing financial support from the state has resulted in worrying levels of debt for new graduates. This pilot study was designed to gain a fresh perspective of how students imagine themselves following graduation. The study used rich pictures (RP) as a methodology to explore student views of life beyond university in the UK and Canada. Content analysis of the RPs provided insights into their thoughts and anxieties about potential challenges for the future. Students presented both positive and negative visions of their future, with success in achieving a respectable performance in their final degree as the key differentiator. The insights gained are discussed in the context of related research into students’ concerns and university initiatives to support students throughout higher education and then into graduate employment. The findings revealed student motivations, hopes and fears which can inform the development of impactful university interventions.