Following the pattern set by the early German Romantics, Kierkegaard conveys many of his insights through literature rather than academic prose. What makes him a valuable member of this tradition is the theory he develops to support it, his so-called “theory of indirect communication.” The most exciting aspect of this theory concerns the alleged importance of indirect communication: Kierkegaard claims that there are some projects only it can accomplish. This paper provides a critical account of two arguments Kierkegaard offers in defense of this claim. The first argument is that he needs to use indirect communication in order to discourage people from losing themselves in the “crowd”. The second argument is that he needs to use it in order to help people out of a “monstrous illusion”. It is shown that while both arguments justify Kierkegaard’s decision to use indirect communication, neither one supports the original claim about its indispensability.