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This thesis studies changing conditions for earning and caring in Italy and Sweden, two cases out of a population of European welfare states facing similar challenges and processes of labor market liberalization affecting conditions for earning, but also for caring. Focus is on how such processes of change affect individual living conditions for earning and caring, as well as on how societies change as a result of changing individual living conditions. The theoretical framework is grounded in feminist institutionalism and multiple equilibria theory, with focus on the interrelation of earning and caring and on how the interaction of formal and informal institutions demarcates and stratifies individual room for maneuver - but also on how such room for maneuver aggregates to affect the evolutionary path of societies. The thesis makes a point of analyzing links between macro and micro levels, in both directions, as a way to offer a fuller and more accurate analysis of how and why societies evolve. It argues that such an analysis requires introducing new analytical tools. To that purpose, the concepts of augmented work family reconciliation, care security, and earning-caring models are defined and identified as key tools for understanding effects on individual living conditions as well as why, and indeed how, societies evolve in the process. Three separate studies are undertaken on each case: one study that analyzes patterns of change in earning and caring over time; a type-case simulation of effects of labor market liberalization on conditions for earning and caring; and an interview study with couples with young children. Together, the three studies allow for an analysis of micro-macro dynamics that enables a new understanding of the two cases. The results highlight gaps in work family reconciliation in the Swedish earning-caring model that other frameworks miss, and how the Italian earning-caring model is rocked at its core as a result of changing conditions for earning. While each earning-caring model is a case in its own right, the analytical framework developed here can fruitfully be applied to the evolution of other cases as well.