The present paper explores the importance of envy and resentment for the development of Kierkegaard´s critique of modernity and the kind of man it reared. Specifically, in the context of Kierkegaard´s thought, envy and resentment are demonstrated as dominant –albeit latent – features of modern moral systems and institutions, and rationality itself as a cognitive theoretical system as well. Kierkegaard´s critique of public sphere and modern subject, which foreshadows some of Heidegger´s best known views (on ‘dictatorship of publicity’, ‘unoriginality’ etc), and the demonstration of similarities and differences with Nietzsche´s considerations and specifically with the latter´s theory of ‘herd morality’ are particularly emphasized. It is particularly important to demonstrate the inability to subsume the primordial moral experience under universal regulative contexts, a view which also has its problems. Kierkegaard´s elaboration of the so called ‘second ethics’ is examined under the light of its opposition to Kantian ethics and philosopher´s attempt to combine the original moral sphere with the original or ‘internal’ development of the subject. Therefore it is argued that, despite a certain degree of one-sidedness in Kierkegaard´s views – and Nietzsche´s secondly-, his critique of the logical foundations of moral systems can also be creative in that, highlighting the limits of regulative moral ventures, it leads to the reconfiguration of our views on morality and the subject itself.