Entrepreneurship amongst women has been a recent occasion. Women have become aware their rights and their work situation. However, women of the middle class are not too eager to alter their role in fear of social backlash. The process is more visible among upper class families in urban cities. This paper focuses on women entrepreneur. Any understanding of Indian women of their identity, and, especially of their role taking and breaking new paths, will be incomplete without a walk down the corridors of Indian history where women have paused, lived and internalized various role models. Some have taken entrepreneurship roles where some have opted for employment, some in entertainment field and some for leadership roles while millions of others have taken the role of ideal stereotyped social roles. The paper slides from the era of fifties to 21st centuries and how transformation has occurred in the women roles. Also the paper talks about the status of women entrepreneurs and the problems faced by them when they ventured out to carve their own niche in the competitive world of business environment.