Incorporating the ‘heteronyms’ of Fernando Pessoa and the ‘pseudonyms’ of Søren Kierkegaard, my project declares a “theatre of the self” that is formed from the multiple personas that are created from their imagination and inspiration. In journeying through and linking these two solitary thinkers’ writings, I present them as troubadours, in the sense of the wandering medieval poets, only this time as troubadours of the imagination. Eternally attached to their respective cities, both writers created what I call a theatre of the self through the various characters in contact and in dialogue with one another, constructing a multitude of selves. The names they create as well as their own names guide and transform their aesthetic and religious vocation, where the imagination of the self becomes more ‘true’ than the actual self, in their life as literature. The peculiar irony is that in their obsession with being honest they continually deceive and construct new selves and perspectives, as Kierkegaard strives for an impossible faith; Pessoa for an impossible resignation. Through this creative and critical juxtaposition of these great modern writers on the Nordic/Protestant and Latin/Catholic peripheries of newly democratic and weakened monarchist countries, I shed new light on this theatre of the self through the troubadour universe of heteronym, pseudonym and orthonym.