The unpredictability of careers in the twenty-first century has prompted the need for individuals to take control (Arnold, 2016). However, in the context of wider societal-level transgender discrimination (Dietert and Dentice, 2009), and especially with regard to authenticity and identity expression (Sawyer et al., 2016), transgender individuals face unique challenges in the workplace; hence career decisions may also be particularly problematic. This chapter explores alternative career choices driven by diversity and resilience where individuals subjectively create and maintain their careers based on individual identity and personal values, through empowerment, enterprise and resilience. A number of transmen who have forged unique career space as transgender artists, performers, models and activists are profiled and discussed. The boundaryless and protean career concepts are critically examined in line with Pringle and Mallon (2003) and an alternative view proposed. lesbian, gay, bisexual, transgender, queer (LGBTQ) careers literature is also explored to contextualize the career environment for transgender individuals.