Due to the ever-changing organizational and societal conditions that make reliance on external definitions of success unworkable or undesirable, subjective career success has remained a critical topic in careers studies. Among the drivers of subjective career success, research has identified personality traits and job resources as essential sources. Grit, in the form of a personality trait, together with I-deals (job resource) and perceptions of employees’ glass ceiling can provide new insights regarding factors, which can heighten employees’ subjective career success. Therefore, the main purpose of the study is to investigate the direct and indirect effect of grit on each dimension of subjective career success via I-deals and perceptions of the glass ceiling. Surveys from 221 female security forces from both private and public sector in Oyo state, Nigeria, were collected and the data was analyzed using the smartPLS. The results showed that grit is positively related to I-deals, glass ceiling and career satisfaction, but not to happiness, psychological wellbeing, and work engagement. I-deals mediated the relationship between grit and subjective career success’ dimensions, while the glass ceiling did not. This study was able to infer that personality trait (grit) has much to relate with how women perceive the existence of the glass ceiling in their organization.