Emerging careers are less linear, safe, and stable and more attentive to the non-professional dimensions of life. People face resistance and obstacles on their careers, namely, regarding gender inequality. The study took an inductive approach with qualitative data collected from ten in-depth semi-structured interviews with leaders in Portuguese organizations, with the aim of understanding the impact of gender on leaders’ career paths and orientations. The thematic analysis identified seven career orientations (school education, challenge, stability, hierarchical progression, own business, people and community, and family), and six gender conditioning (functional segregation, male leadership, sexual and moral assessment of women, resistance to male interest by the family, access and representation mechanisms, and work–family articulation). Our results show a reality not free of gender inequalities, which forces women to give twice to be recognized as having equal value to men. Organizations must ensure equal opportunities and removing any forms of gender-based discrimination.