Critiques of neoliberal capitalism have offered a rich vocabulary for the analysis of the political economy of literacy across professional, public, and classroom contexts. Since the Great Recession, commonplaces about work-readiness have been conditioned by economic precarity and changes to the social contract of work that blur the lines between professionalization and exploitation. Looking beyond the confines of the neoliberal present, the uncertain future of work for our undergraduate students will be shaped by what the World Economic Forum describes as the “double-disruption” of the pandemic and the rise of automation. Whereas neoliberal critique offers a vocabulary for describing many job seekers’ experience of the present, this article seeks to recover an element of “literacy hope” (Wan) by looking to speculative and utopian postcapitalist theory to inform and challenge career guidance conversations with students in writing studies. By framing the future as a resource in the rhetorical constitution of present-day workers, this article advances an inquiry-focused career-guidance pedagogy that asks: How do our assumptions about the future of work inform our relationships with employers and each other in the present?