This mixed-methods study investigated self-esteem and social comparison during middle childhood in two distinct communities: a Chicago public-housing development and a group of refugee camps near Luanda, capital of the Republic of Angola. Building on separate bodies of existing research about childhood in marginalized communities, self-esteem, and social comparison, I present an interpretive account of how conceptions of childhood associate with psychosocial characteristics in these two communities. In the Chicago community, an intense emphasis on accelerating childhood toward adult characteristics corresponded with accentuating high self-esteem and extremely competitive social comparison. In contrast, the Angolan community conceptualized childhood as distinct from adulthood in ways that prioritized role achievement above self-esteem and encouraged integrative social comparison. The comparison of the cultures of childhood in these two communities, which shared relative poverty and were regularly targeted by external agencies for interventions, has implications for understanding child development and psychological adaptation in marginalized communities.