Educational researchers identify the transition from post-secondary education to the labour market as a critical point for the success of the student, and for society more broadly. This transition is often explored as a distinct phase between education and work that can be assessed based on pre-determined outcomes (i.e. employment, income). From this perspective, it is the responsibility of individual students to effectively commodify themselves and navigate their transition into employment. This focus on individual responsibility fails to question social mobility discourse and current labour market realities that significantly influence transition. In order to re-conceptualise transition, I deconstruct social mobility discourse as the foundation of transition research. Then, I draw on narratives of social service workers in British Columbia, Canada, to complexify transition and allow for more nuanced research. The narratives contradict dominant conceptualisations of transition, critiquing transition as a linear process that can be assessed through economic indicators. Recognising transition as a continual process that is influenced by a multiplicity of factors opens new ways to research. Research exploring the nuance of transition moves away from a deficit-focused, intervention approach focused on students, to critically exploring education, the labour market, and the relationship between school and work.