Retiring is associated with increased risk of cognitive decline (e.g., Bonsang, Adam, & Perelman, 2012; Wickrama, O'Neal, Kwag, & Lee, 2013). However, little is known about the moderating role of motivational and demographic factors that are implicated in adaptive development and the retirement transition process. We used data from the Midlife in the United States Study (n = 732, Mage = 57, SD = 5.76, 50% female) to examine whether the association between retirement and cognitive decline depended on a key motivation factor (goal disengagement) in propensity score matched samples of older retirees and employees. We explored whether these effects were further moderated by gender. Results showed that those who retired (vs. remained employed) experienced steeper 9-year declines in episodic memory (b = -.41, p = .001) only if they were high in goal disengagement and female. Findings are consistent with theories of lifespan development and cognitive aging and provide initial evidence that retirement may be associated with increased cognitive declines for only certain individuals prone to disengage from highly challenging activities and goal pursuits. (PsycInfo Database Record (c) 2020 APA, all rights reserved).