The present work consists in the analysis of Sérgio Buarque de Holanda’s literary criticism and essays since the beginning of 1920’s through 1936, year of the Raízes do Brasil first edition. The argument tries to establish a particular connection between the role of critic under the modernism movement, which he played in the early years, and the formulation of the questions running through his 1936 book. However, this relationship demands a particular understanding of his participation in the modernism movement, as it was two folded: the defense of an aesthetic renew and a concern for the tradition setting in Brazilian society. The dialogue with such authors as Alceu Amoroso Lima and Mário de Andrade, and a later trip to Germany, led Sergio Buarque to consolidate his modernism stances and to refine his concerns about Brazilian peculiar development. This work intends to discuss this trajectory in the author’s thought, culminating in the analysis of the ideas of fortune and adaptation; that was revealed as a strategy to understand some arguments in Raízes outside the mechanical weberian scheme (of ideal types and the process of world rationalization) to comprehend the Portuguese colonization in Brazil.