Women with managerial careers are significantly less satisfied with their life than their male counterparts. Why? In a representative German panel dataset (GSOEP) we find biological constraints and substitutive mechanisms determining the subjective well-being of female managers. Women’s terminated fertility has a negative impact on women’s life satisfaction between the ages of 35 and 45, when managerial careers usually take off. Money and spare time can compensate for this biological difference. But to maintain an equivalent level of happiness, women need to be compensated by much more income for each hour of spare time given up than men do. So, in order to reach better gender equality in leadership positions, women must be either paid higher incomes (on average around 10%) or must be incentivized with more spare time than men. In the conclusion, we speculate on a new mix of carrots and sticks for advanced careers in order to boost female representation in leadership positions.