This chapter responds to recent Management and Organization Studies (MOS) calls to rework gender. The mainstream of MOS research performs prescriptive gender analysis that misses out on fluid social realities and flexible identities. Globalization nullifies dichotomies. The chapter builds the case for the analytical dissociation of bi-gender and the reorganization of opportunities and careers. It offers a conceptual alternative that opens MOS analysis to be responsive to contemporary social dynamics. The prevailing bi-gender category carries the values of European pre-industrial and industrial societies. European societies are currently transitioning from industrial economies to information economies. The practices of worldwide operating organizations have moved beyond the sex/gender and man/woman divides. The chapter demonstrates how old thinking (re)produces inequalities in future global transpersonal leadership qualities and behaviors. It then broadens the bi-gender spectrum towards a continuum of multiple combinations of differing bodily/identifying/behavioral practices and a range of multiple enactments.