In this paper, I propose second-order design fictioning as a way of reframing the hegemonic fictions built around technology, work, and design. These forms of progress fictions are further amplified by uncritical developments in cybernetic technologies that have a complex and often problematic relationship to discourses around the politics of innovation and acceleration.Projects related to the speculation of post-work futures within a design studio and seminar are used as a heuristic to engage broader theoretical questions on the reductive ways in which the question of changes in technologies (human-machine relationships) are addressed in the context of the transition imagination towards alternative work futures. Within these projects, engaging frictions, i.e., questions concerning difference and sense-making in sites of disruption, are further problematized. To define the notion of a second-order in design fictioning, the paper draws on modes of engaging systemic complexity as theorised within recent discussions in design cybernetics, critical cybernetics, and Gregory Bateson's work on meta-communicational frames. Second-order design fictioning, as proposed here, delinks the better-known concept of design fiction-a methodological tool often used in the imagination of futures-from its preoccupation with objects, technology, and technocratically projected views of the future and innovation. It is hoped that second-order design fictioning would enable a better focus on the complex politics of the changing value frameworks (fictions) that drive these concepts.