Conversations on authentic leadership development all too often are devoid of contextual considerations. Little attention is placed on how authentic leadership is actualized by individuals who hold marginalized and minoritized social identities and/or whose lived experiences diverge from the privileged majority; and therefore, must strategically negotiate facets of self to "do leadership." This article illustrates how facets of one's lived experiences, social identities, and worldviews significantly shape and guide how "authentic" leaders show up and practice leadership authentically. This article highlights how elements like code-switching and impression management challenge preconceived notions of what it means to be "good" and "genuine" as a leader to better understand how a theory like authentic leadership gets operationalized. This deeper analysis of authentic leadership provides a nuanced perspective to inform curricular and co-curricular designs that are mindful of context, power, and privilege as well as the uniqueness of the individual.