The relevance of women’s participation in the workforce cannot be overemphasized. Studies have proved beyond reasonable conviction that the quality of decision making and long-term sustainability of any given business is positively impacted by participation of women professionals. As of December 2023, the total workforce in the Indian IT/ITES/BPO is around 4.5 million (study-2023, n.d.). Of this, women professionals comprise 34% of their workforce. However, a majority of them are found at the entry level. A cause for concern is that almost 48% of the women professionals in IT attrite before they reach 30 years of age. (Economics Times-June, n.d.) This phenomenon is primarily due to the challenges faced by working women in the pursuit of their careers. This high workforce pipeline leakage of women professionals in the IT sector is disquieting as huge investments are made in training these women and rendering them productive. Hence ensuring their continued existence by way of talent retention assumes significance. Career aspirations are the vision of one’s future and are fundamental building blocks for a successful career. These aspirations are shaped during the formative years and may undergo transformation according to the experiences of the working professional. This study attempts to understand the factors that impact career aspirations and challenges faced by women professionals in the pursuit of their aspirations. The study also examines the difference in the paths pursued by certain successful women professionals in contrast to the average working women. The study has adopted a mixed method approach involving extensive literature review, survey method and case studies. Respondents comprised primarily working women professionals from IT, ITES and BPO. A structured questionnaire was used to gather data from 414 women working professionals in IT, ITES & BPO. The study adopted snowball sampling and convenience sampling. From among the respondents, successful women professionals were identified and interview schedules were conducted to generate additional facets of undiscovered parameters and a model was developed. Under the qualitative case study method, an unstructured, free-wheeling discussions was held with 6 women professionals. The findings from these case studies were extracted which in turn helped to test the final model. Chi square was applied as a measure of multiple hypothesis. In most cases marriage and related responsibilities were the major life events that resulted in career break.