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Increased life expectancy in conjunction with record numbers of Baby Boomers departing the workforce yields a population that will spend a great deal of time retired. After decades of labor force participation, it is hardly surprising that one’s identity is typically enmeshed with occupation, even after exiting the formal labor market. In retirement, individuals often face a disorienting role loss and must navigate emotional, financial, physical, and familial ramifications. This study explores how the varied experiences men and women have during their working lives influence well-being and identity in retirement. Existing narratives imply this role loss would pose a greater identity threat to men exiting high status occupations who consequently have lower well-being in retirement. Drawing on 20 in-depth interviews conducted in the California Bay Area, I find that women exiting successful careers or who strongly associate with their professional identity surprisingly reported more difficulties adjusting to retirement than men and employ different transitional coping strategies. For most, letting go of a professional role is challenging in its own right. But for women, losing a professional identity forged amidst labor market discrimination and structural inequality poses unique retirement challenges, which can negatively impact well-being in later life.