Charles Taylor rendered a detailed and extensive analysis of the cultural ethos shaped by modernism within western culture from Christendom through the late 20th century. His philosophical work sought to understand identity development and social formation through the paradigm shifts generated by modernism. Taylor posited secularism, which has gained momentum in the late twentieth century, threatens an individual’s capacity to find authenticity or experience transcendence. The concepts of modernism Taylor addressed offer a greater understanding of the epistemological and ontological changes that have reshaped, and continue to reshape, western society and the individual’s experience within it. The purpose of this analysis was to articulate and analyze the constructs central to Taylor’s major works in relation to authentic leadership theory to determine the theory’s validity or limitations. Taylor and authentic leadership theory value similar concepts and building blocks for authenticity but interpret the terms of necessary characteristics quite differently. The method for developing an authentic self and leader are in opposition to the extent authentic leadership theory validates Taylor’s arguments concerning the malaises of modernism that obstruct true authenticity.