The transition from youth to adulthood in African nations has changed markedly in recent years. Social and economic challenges often lead to the creation of a disengaged and alienated generation struggling to participate actively in society. Drawing on the personalized accounts of a group of youth leaders experiencing such conditions, this paper presents empirical findings from a small-scale qualitative study of one Sport for Development and Peace (SDP) initiative that, through various community-based projects, aims to provide personal, social, and educational support for young people in Mzuzu, a city in northern Malawi. The paper seeks to uncover some of the reasons behind youth disengagement within this particular context and explores how empowerment-based mentoring is used by youth leaders to bring about change in the lives of the young people with whom they work. The paper concludes that amid the wider tensions and anxieties of youth transition in sub-Saharan Africa, strategic and intentional relationship building (through mentoring) can provide a catalyst for personal development, intergenerational connection, and social change.