Background: Existing research shows that well-being in midlife is shaped by various life domains that are gendered in context specific ways and unfold dynamically across different stages of life, notably education levels, career and job statuses, as well as interpersonal factors. Current research reveals that gendered educational and employment trajectories significantly influence midlife well-being. Also, continuous employment positively impacts both men and women’s satisfaction with life. Conversely, unstable employment histories have cumulative negative effects, with longer spells of unemployment exacerbating dissatisfaction. Aim: We aim to address gaps in the existing literature by providing insights into the diverse effects of education-work trajectories on well-being. To do so, we examine well-being in midlife from a gendered comparative life course perspective by investigating well-being inequalities among women and men with diverse educational and employment trajectories over adulthood. By focusing on gender differences in satisfaction with life in mid-adulthood and situating them in welfare state policy contexts (Canada and Germany), we examine the interplay between individual experiences and societal structures in determining the social distribution of well-being. Method and Data: Two longitudinal studies, the German LifE and the Canadian Paths on Life’s Way, spanning approximately 30 years (from ages 16 to 46), provide data for our analyses. Partial proportional odds models are employed for statistical analyses using clusters of proximate trajectories derived by previous sequence analysis. This allows for comparisons between both countries and across genders. Results: Accounting for individual characteristics, family factors, dynamic life course variables over adulthood, and static employment characteristics in midlife, we demonstrate that continuous full-time employment does not universally boost life satisfaction for German and Canadian men and women. Rather, patterns of inequality emerge related to levels of education and family factors, with women reporting increased odds of high levels of wellbeing when in continuous part-time employment. Conclusion: The findings highlight the complex relationship between education, employment, gender, and welfare states in shaping inequalities in well-being in mid-adulthood. This study has strong implications for the social policy structures in place allowing families to balance work and family obligations.