This study investigates whether employment/education histories by age 30 are associated with the cumulated fertility at age 30 and with the completed fertility at age 45. We use data from the ISTAT survey “Families and Social Subjects” and adopted a sequence analysis approach to describe the employment/education histories of individuals aged 45–60, while accounting for complex time‐related interdependencies among employment episodes. We compare different sequences by using optimal matching methods and perform cluster analysis to identify the most frequent typologies of employment/education trajectories. Preliminary results from Poisson regression models suggest that men and women entering the labor market at a later age have, on average, fewer children by age 30 compared to those with other employment/education trajectories. However, this negative association disappears when we analyze fertility at age 45, suggesting that individuals who postpone their entrance into the labor market are able to recover in the long run. The fertility behaviors of individuals with uncertain employment histories do not differ from those of people with more stable employment histories. Lastly, women who never worked tend to be characterized by larger families at age 30 but not at age 45. This study shows the importance of analyzing the complex interplay of employment episodes in early adulthood to predict completed fertility later in life.