The topic of this paper is the differences between women entrepreneurs and women in managerial positions within companies, with an emphasis on the variances between two countries: the Republic of Croatia and the Republic of Serbia. The first part of the paper defines the development and concept of women's entrepreneurship, as well as the obstacles and opportunities for the development of women entrepreneurs. Additionally, the concluding section of the first part describes entrepreneurial activities in the territories of the Republic of Croatia and the Republic of Serbia. The second part of the paper illustrates the similarities and differences in business between the female and male leadership styles. Drawing on relevant literature, it presents differences and future perspectives for women managers within Croatia, Serbia, the European Union, and the rest of the world. Furthermore, the paper defines the objectives of women's entrepreneurship development and provides examples of female entrepreneurs in the Republic of Croatia and the Republic of Serbia. The aim of this paper is based on two research questions: What are the differences in motivation between women who have decided to start their own business and women who have chosen to remain and progress within corporations? What were the key obstacles faced by women entrepreneurs compared to women in managerial positions? The research questions were answered by conducting interviews with women entrepreneurs and women in managerial positions in the Republic of Croatia and the Republic of Serbia. The responses obtained from the respondents were analyzed and commented upon.