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This exploratory qualitative study seeks to describe and understand the career decision-making process of unemployed American women who make up the younger cohort of the baby boom generation, namely those born between 1955 and 1964. Career decision making is a complex process involving a number of generational characteristics as well as personal and economic considerations. Unemployment further complicates this process, especially in the decade prior to receiving retirement benefits. This study uses interpretative phenomenological analysis to analyze semi-structured interviews with eight unemployed younger baby boom women to investigate how their thoughts, assumptions, and opinions affect their career decision-making experience. Bronfenbrenner’s bioecological model (2005), Erikson’s lifespan theory (1959), and selected career development theories provide lenses through which these women’s experiences can be understood. Eight themes emerged from the data, including the following: unemployment as a preparation period; career aspirations; digital natives; age discrimination; bioecological systems influence; generativity vs. stagnation; identity expressed in career decision making; and influence of intuition, chance, and personal factors. The findings suggest that the women used the period of unemployment to become self-aware and thoughtful about future career decision making, and enhance their computer as well as career decision making skills. Implications for theory and counseling practice as well as suggestions for future research are provided.