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The very idea of progress, or lack of it, indicates something about the role machines can play in one’s life. Notions about how technology can be used—to improve, subvert, destroy, extend, or interrogate—reveal the interplay of human and machine. What notion of progress might adequately capture the complex interdependence of human and machine in a way that illuminates our current predicament? To ask whether specific events make things better or worse does not reveal what guides our notion of better and worse, what crucial premises, to quote Robert Nisbet (1979), guide our assumptions. In the 21st century, a notion of progress that captures current experience must in some way address randomness, as well as design. We must think again about past and future, about what it might mean to make progress in a world defined by randomness, characterized by uncertainty—a world rich with possibilities and shadowed by dread.