First and foremost, this article deals with the process of reading and interpreting the oeuvre of the Portuguese poet Fernando Pessoa. Furthermore, it wants to examine whether freudo-lacanian psychoanalysis anno 2008 is still relevant for analysing and unlocking the personality structure of an author. By means of four central remarks this article describes the practical and theoretical pitfalls the interpreter must be aware of if he to avoid losing sight of the oeuvre and person of Pessoa. The article ends with illustrating how psychoanalysis, in order to analyse the personality of Pessoa based on some biographical elements and his literary inheritance, forces the interpreter into a continuing process of reflection. In conclusion the author stresses the importance of an attitude that does not trivialize the gap between the (symbolic) dimensions of knowledge and the (real) dimension of truth that lies beyond every theory.