This paper studies eight ascetical poems by Saint John of the Cross, from both a literary point of view and also as an inverse description. Therefore, the paradoxical descriptions of ecstasy and the subsequent acquisition of wisdom become an inverse philosophical reflection. The method of analysis is semiotic and textual interpretative, which renders possible a personal explicative hypothesis. The conclusion is that this work relies on paradox and aporia, which generates “inverse semiosis”: signs are not created by what they are, but by what they are not. Although the poems are not always perfect, they reveal a great knowledge of the language. The term “saintjoanine glosa” is proposed for a strophe consisting of nine eight-syllable verses, rhyming A, B, B, A, B, C, D, C, D, which is very infrequent in Spanish poetry. Poetry is, then, extremely efficient in expressing these ambiguities. So literature reaches degree of infiniteness, setting an aesthetic of the impossible and semiotics reaches a crossroad: to be holistic or not to be. We will use our own--and very free---translations into English. Literal equivalence is preferred instead of rhythm and rhyme. In this paper a few Spanish archaisms are kept: spellings as “caça” or “sciencia” have a strictly diachronic value, and meaning is not betrayed if they are written in a modern way. However, updating forms such as “aquesta”, which appears in the poem called “Vivo sin vivir en mí” and replacing it by the modern demonstrative “esta” would imply an unacceptable alteration in the syllable structure, that is why it is preserved. In the translations, we have quoted the author’s name as “SJC” in order to save space.