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Purpose in life has been shown to affect important outcomes related to healthy aging. However, quantitative studies have consistently found lower purpose in life among older adults. A qualitative inquiry into purpose in life may offer insights into why there appears to be a decline in later life, and for whom. This study investigated two waves of life narratives from late midlife women to explore how they expressed meaning and purpose regarding their life paths. White and Black women (N = 16) with higher and lower purpose in life were sampled based on a prior quantitative study (Ko, Hooker, Geldhof, & McAdams, 2016). Using a grounded theory approach and a life course perspective lens, we analyzed two waves of life stories over five years to understand how participants experienced their purposes in life over time. Three common themes emerged including the centrality of family relationships, the negotiation of work, and the pursuit of agency. Those with higher and lower purpose in life scores varied in how they defined and enacted purpose in life based on prior and current life experiences. Being proactive in directing one’s life course was shown to differentiate those with higher versus lower purpose in life. In transitions into older adulthood, having a proactive approach to the world may be salient for a purposeful aging process.