Dealing with two complex and decisive authors that have been important for humanistic encounters, the research in this paper presents an in-depth study of two attempts at biographies. With two different methodological approaches to the life and work of the poet Dante Alighieri and the humanist and theologian St Maximus the Greek, we introduce the complexity of the author's creative process as well as of the historical moment of the period when each lived. We also addressed the problem of the valuation of the Medieval and Renaissance period, because we considered the presented authors to be valid examples for the beginning of the new era of thinking in the history and culture of mankind. Further, the article seeks a precise graphic solution for visualizing the relationship between the creative process and the biographical data. Moreover, for deeper understanding of the theologically inspired and conducted poetic works of the authors, a triangle structure is proposed within which the basic idea of the authors' will and their artistic vision could be expressed.