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In a famous essay written in 1782, Immanuel Kant argued that it is only when a man is free to make his own choices that he can be said to be enlightened (pp. 58–65). In his opinion, "enlightened' freedom was composed of three components: the ability to think for oneself; the ability to think from the standpoint of others; and, lastly, the capacity to think and act in concert with one's beliefs. In this chapter, I examine how Enlightenment ideas about freedom related differently to men and women, especially in regards to societal notions of authenticity and leadership. I focus on Western Europe, since this was where modern ideas surrounding authenticity were initially formulated (Taylor, 1991). In tracing authenticity's modern underpinnings to the emergence of bourgeois selfhood, I show how gendered notions of what constituted right conduct served to enhance men's freedom while simultaneously restricting women's agency.