In this chapter, we focus on speculation that is future-oriented. We characterize this aspect of speculation as resistant or critical towards prevalent, dominant, or probable future trajectories, that interweave politics, technologies, and cultures by offering propositional futures to create or maintain space for alternatives. We describe the experiential alternative of para-functional things as a common strategy for the designing and creating of artifacts and systems. We begin with Italian Radical Design through to present-day work, including inquiries into participatory Afrofuturism, rethinking the internet, and resistance of gender norms. We apply our criteria of leaps of imagination, diverse epistemologies, ethical reflexivity, and experiential alternatives to draw out the particulars of speculation as well as the strategies used to create experiential alternatives. Arguing that the characteristics of speculation are important to broader research in design, we explore the interconnectedness of speculation in the vision of ubiquitous computing, critical literature reviews, and participatory design methods.