Using Life in Transition Survey (LiTS) data for 27 transition countries, overall we find a gender gap of 6.5 percentage points in self-employment against women. Higher educated young women are less likely to start a business except ethnic minority group and European Union region. Membership in a civic group helps only men though affiliation with a political party is favorable for women to start a business. A professional woman is 30 percentage points more likely to start a business than salaried job. Other findings also have higher implication for policy purpose, like fertility decisions are positively correlated being self-employed for women. Self employed women especially in Baltic and Commonwealth of Independent States (middle income) more likely to pay bribe for official work and both sexes in large proportion are self-employed in the field does not match with their field of education.