Studies on the life course process of labor market inequality have shown that occupational status diverges early in one’s career and remains stable in the midlife period; however, the long-term the trajectory of one’s career, including the pensionable age, is still unclear. Using retrospective data matching with occupational information networks in Japan, I describe how analytical skill usage, which is a detailed component of class mobility, changes or remains stable from 20 to 69 years of age. I find that careers are more volatile in later life and that volatility appears as a decrease in skill level. Men who enjoy greater opportunities for training and promotion within a firm experience a significant decrease in analytical skill usage compared with women. The educational difference in analytical skill usage is persistent in later life, implying that general human capital has a durable benefit in later life. The results highlight that the divergent pathways in one’s early career do not necessarily continue in later life. Rather, the advantage acquired in one’s early career can be lost later in life, especially for men.