Around the world employment of women on an equal bases allows companies, industries and countries to make better use of the available talent pool, generally with potential growth implication. In Japan, since 2013, Prime Minister Shinzo Abe has been a ceaseless advocate for the increase in the number of female employees for the revival of the economy, and many governmental programs in support of working women have been put in place. However, the traditional Japanese management systems of lifetime employment, enterprise unions, seniority systems, together with a group-oriented and risk-adverse orientation make things change slowly. In Romania, the second country analyzed in this article, women entrepreneurs also face professional stereotypes, difficulties in getting specific jobs, traditional prejudices and a collective mentality related to women’s place in society. This article explores and compares how Romanian and Japanese cultures, societies, and economies have either encouraged, or discouraged, the growth of female entrepreneurship on their own territories, and analyzes how the best emerging female executives can be supported in the future in order to maximize their potential. The analysis is based on the data provided by OECD, the World Bank, the Global entrepreneurship monitor, Japan statistics, the legislations of the two countries and the literature related to the two social environments. The findings indicate that although there are many similarities between the two countries, the percentage of female executives in Japan is much smaller than the one in Romania. This is due to the fact that Japan, with all the governmental programs in action, for the moment, still has a stricter social and work environment, a weaker maternity and childcare legislation and a higher gender gap.