This paper investigates the compatibility of Hegel’s analyses of the mechanization of work in industrial society with Hegel’s notion of freedom as rational self-determination. Work as such is for Hegel a crucial moment on the way to a more complete realization of human freedom, but, as I maintain with Adorno, the technological developments of the last two centuries raise the question of whether the nature of work itself has changed since the industrial revolution. In his Jena lectures, Hegel recognized significant (...) problems that the mechanization of work poses for human freedom that—on my assessment—his later, mature thought does not sufficiently address. One finds, however, a more comprehensive depiction of the same worries that Hegel mentioned in his Jena lectures in Adorno’s critique of the dominant forms of labor in contemporary society and his understanding of technological rationality, which according to Adorno, dominates the contemporary world. I suggest, furthermore, that juxtaposing Hegel’s and Adorno’s thoughts on technology and the mechanization of work reveals Adorno’s philosophy of technology to be an extension, rather than a critique, of the spirit of Hegel’s own philosophical project as immanent critique of the necessary entailments of any given concept. (shrink)