This study explored the work experiences of individuals who have started transitioning from their biological sex to a different gender expression through 18 interviews of transgender-identified individuals. Thirteen of the participants identified as male-to-female transsexuals, 2 participants identified as female-to-male transsexuals, 2 participants identified as female-bodied gender queer individuals, and 1 participant identified as a biological male cross-dresser. Using a grounded theory (K. Charmaz, 2006) approach, 2 separate work experience models emerged: (a) the process of gender transitioning at work and (b) the career decision-making process. The 3 phases of the first model included a pretransition phase, during the transition phase, and posttransition phase. Within these 3 phases, the following 5 major themes emerged: preparation for the work transition, coming out at work, presentation and appearance at work, others' reactions at work, and affective/coping experiences related to work. The second model resulted in 6 major themes related to career decision making: occupational barriers, occupational prospects, occupational aspirations, taking action, occupational gratification, and contextual influences. (Contains 2 tables and 2 figures.)