Objectives: Successful aging has been identified as an important emphasis for people living with human immunodeficiency virus (HIV). Little is known about how this population conceptualizes aging successfully and how this relates to generativity. This qualitative study examined the importance of generativity among 30 HIV-positive older adults to determine the role of generativity in successful aging. Method: Participants aged 50+ years were recruited in Ontario, Canada, through acquired immunodeficiency syndrome (AIDS) service organizations, clinics, and community agencies. Qualitative interviews were analyzed to explore strategies participants employed to engage in successful aging within their own personal context. Results: Participants saw themselves as pioneers and mentors, helping others to navigate the landscape of aging with HIV. Four themes were identified through consensus including (a) reciprocity, (b) mentoring, (c) pioneerism, and (d) connecting through volunteerism. Discussion: Interventions that promote intergenerational connections, community involvement, and generative acts within the HIV community can facilitate successful aging among older adults living with HIV/AIDS. © The Author(s) 2018.