Within multiple social roles, such as careers and personal relationships, psychologists are encouraged to maintain their authenticity. Although the concept of authenticity has a lengthy history in the philosophy and literary fields, only in the last decade have researchers begun empirically studying this unique, yet vague, concept. This study sought to explore and understand what experiences, issues, and concerns psychologists encounter in their efforts to live authentically. A purposeful sample consisted of 17 psychologists, who were individually interviewed. Utilizing a qualitative research design, 328 significant statements were extracted and grouped together, resulting in five emergent themes specifically related to personal and social, nontherapeutic contexts. Participants described how their psychological-mindedness adds to complexity of separating the person from the therapist during encounters with others. They believed that self-exploration, self-awareness, and self-acceptance were important in attaining one's authenticity. Concepts of culture and gender influences, psychological-mindedness, and consistency in social roles were discussed as related to authenticity. Last, participants indicated feeling the most authentic with close friendships, significant others, and family members, and less authentic in casual and/or collegial-professional roles.