Historically, males from low socio-economic backgrounds have been a difficult demographic for educators to reach and engage. Despite efforts to widen participation in Australia, males who would be considered 'first-in-family', remain severely underrepresented in higher education. For those who do attend, they often encounter significant barriers and are at a higher risk of attrition. Experiences with employment can be a determiner of their success at university both in terms of informing or reaffirming their prospects for future employment. While recent policies in Australia have sought to integrate working-integrated learning (WIL) into university studies, these are not available to all students thus opportunities to develop skills and attributes through WIL remains a fragmented picture. As a result, we are witnessing many young people who are concerned about their future employability seeking out non-formal WIL opportunities to bolster their CVs. This paper explores the motivations of first-in-family males to pursue non-formal WIL opportunities and the effects these endeavours had upon their aspirations.