Technological visions of the future generally come in one of two flavors. In a utopian dream, technology seamlessly integrates into the fabric of everyday life. On the other end of the spectrum lie visions of dystopia, often centered around the havoc a sentient artificial intelligence can cause when it inevitably determines that humans are our most significant threat. This essay attempts to illuminate a bridge between what is and what ought to be through a critical analysis of automation and technological innovation. We trace efforts to deskill labor, from early mechanization through current efforts to design a “future-proof” smart city. To do this, we examine automation through Haraway’s cyborg lens, the postmodernist assemblage of contradictory components. Who is benefitting from automation? Who is harmed by it? In following with the theme of our essay, we also follow up by asking, who ought to? To explore this question, we review efforts to build economic infrastructure from the bottom-up in a process that emphasizes upskilling rather than deskilling labor.