Hegel’s master-slave dialectic has often been used as a model or starting point for later theories about emancipation and subversive changes in society. But one often overlooks the fact that the chapter in The Phenomenology of Spirit ends in disaster, as Judith Butler remarks. Instead of realising freedom, the consciousness gets entangled in self debasing activities in its attempts to master the unrelenting principles of the abstract freedom. We get “the unhappy consciousness”. This development is further examined in this essay in dialog with Butler and Slavoj Žižek, amongst others. Focus is placed on the concept of stubborn attachment (Eigensinnigkeit) and the paradoxical role this plays in the development towards freedom. What are the possibilities for transcending a detrimental relationship like the one between slave and master according to the Hegelian dialectic? A conclusion drawn here is that the two chapters about the master and the slave and “the unhappy consciousness” together exemplify Hegel’s assertion of the necessity of having both the abstract, universal freedom – which often take extreme expressions in its one-sidedness – and its concrete correspondence. This aspect is easily overlooked with Butler’s Foucault-inspired view on resistance – a suggestion that also will be further developed in the following.