This article analyzes how men's and women's careers are influenced by path dependence, different career determinants, and generation gaps. The analysis is based on panel data from AFF's leadership surveys, and follows a representative sample of Norwegian managers in the middle phase of their careers between 1999 and 2011. The data shows that male managers start their careers in higher managerial positions and invest longer hours in their jobs than their female colleagues. Women who are careerists do succeed, however, in reducing some of men's advantage later on. Higher education and jobs in private sector firms are significant determinants of women's chances for reaching a top management position. For male managers it is seemingly more important to start their careers at high levels, and to invest in future promotion opportunities by working long hours. Young female managers at the outset of their careers in 2011 started in higher positions than those at the same age twelve years earlier. The article demonstrates how panel analysis and cohort analysis may bring new insights into men's and women's career trajectories, and concludes by suggesting how such approaches may be further developed in future research.