This paper engages with Todd McGowan’s Emancipation after Hegel by changing the perspective regarding the role that contradiction plays in cultivating emancipatory praxis; a curiously novel endeavor, which is to be considered an offspring of the German idealistic tradition, having Hegel as its procreator. Here, my intention is not to indicate an inherent problem with this premise, but to think through an impasse that is embedded in the bowels of dialectical thinking. While McGowan is adamantly advocating contradiction in the name of emancipation, there is an imposing realm left untouched if abridged to just this. As a (ontological) deadlock, emancipation has to be thought as immanently tied to language, which is in Hegel’s mind the purest speculative form. Furthermore, in contrast to the contemporary use of speculation as a financial practice, Hegel regards the commitment to a speculative spirit as thinking in the terms of a life worth less than meaning. It is at this conjuncture that I, on one hand, accordingly aim to broaden the debate on emancipation through an unfolding of the framework of contradiction itself, and on the other, to distill the process according to which language is able to form thoughts from empty words.