This study explores transformations that occurred from the age of reason to postmodernism. It conducts an analysis of these transformations in light of questions that contributed to their formation, based on the hypothesis of a close connection between the synthesis of foundational questions and transformations. The study observes these transformations by extrapolating the foundational questions and their effects, taking into account temporal periodization from the age of reason to the postmodern period. These foundational questions are threefold: Through what method was the Age of Reason established? How did enlightenment establish modernity? And how did the questions of value and advantage establish postmodernism? The study is based on an interdisciplinary approach between philosophical and literary thought in the nineteenth and twentieth centuries.