There is a conception that contemporary work lives become ever more complex. Pioneering research has indicated that work lives have indeed become more complex, yet at a modestly increasing pace. This paper uses Swedish registry data across an exceptionally long time period, including cohorts born from 1931 to 1983. The following conclusions are drawn using state-of-the-art methods of measuring sequence complexity. For early-careers, an increasing complexity trend is evident between the 1950s and 1960s birth cohorts, yet complexity fluctuates around a stable trend for the 1970s birth cohorts and onward. For mid-careers, which are considerably more stable on average, complexity has decreased among women born between the 1930s and the early-1950s. However, the opposite trend holds true for men, resulting in a gender convergence in work complexity. We observe a subsequent standstill of the mid-career complexity trend across both genders, followed by a modest decline for the last observed cohorts. Analyses point to educational expansion as an important driver of the initial increase of early-career complexity. Taken together, this study affirms an initial shift to more work life complexity in the twentieth century, yet we find no unidirectional trend toward more complexity over the last decades.