Despite his persistent polemics against the Hegelian ‘speculative’ philosophy, Kierkegaard recognized his own ‘enigmatic respect for Hegel’, and one of his pseudonyms (Johannes Climacus) even acknowledged that his ‘own energies are for the most part consecrated to the service’ of speculation. Nowhere are Kierkegaard's energies more productively devoted to this service than in the work of his last pseudonym, Anti-Climacus, The Sickness Unto Death. In this essay, I argue that not only are there structural parallels between the anatomy of despair in The Sickness Unto Death and the analysis of the ‘unhappy consciousness’ in Hegel's Phenomenology, but that there are striking parallels in terms of the actual content of the respective accounts. I develop these parallels in order, finally, to reconsider the terrain of difference between Kierkegaard's Christian therapeutics of despair and Hegel's phenomenological therapeutics.