Age is critical as a resource in a theatrical career, for it offers the energy and looks necessary for drawing audiences and attracting financial supporters to sustain one’s career and socio-economic survival. The discussion in this chapter aims at establishing the experiential differences of male and female theatre performers concerning the effects of the aging process on their theatrical careers. It concentrates on Kampala-based theatre performers as respondents. The discussion emphasizes “the process” of aging, in other words, the addition of years to one’s life and to his or her career, rather than the state of being “old.” Using Amartya Sen’s conceptualization of development, the chapter explores how aging in some ways opens up  socio-economic opportunities for some Ugandan theatre performers and yet for others it brings about greater constraints to their socio-economic survival in the industry. Data was collected through in-depth interviews with five male and five female respondents. It reflected that in general aging is more constraining than rewarding to a theatrical career. Female more than male theatre performers feel the brunt of its negative effect because of existing gendered stereotypes and perceptions tainted with gender discrimination.