Dr. Ladge will be discussing the findings from her co-authored study that examines how the gender expression of transgender individuals evolves as they transition in the context of work. In this manuscript, we draw from interviews with 25 transgender employees conducted at four points in time over a two-year period as they initiate, perform, and continue their gender transition. Contributing to the literature on authenticity and identity transitions, our findings challenge the assumptions that individuals know how to express an authentic self and that authenticity has an endpoint by pointing to the evolving and relational nature of authenticity that involves a trial-and-error approach in which transgender individuals learn to become authentic as they engage in various forms of gender performativity. Further, we position authenticity as a continuum, as individuals may temper their gender expression to elicit acceptance and express a gender that feels “authentic enough” as they contend with the impact of prevailing gender norms and expectations in the workplace. Finally, the findings suggest that the identity transition process evolves in a non-linear way and involves a dynamic interplay between the desire to express one’s gender in a way that feels authentic and the desire to feel accepted by others.