This article highlights historical and contemporary obstacles for African Americans toward parenting. The authors’ hope is to move beyond the “neutrality” or the “one size fits all” dialogue within the traditional Adlerian parenting model that has been discussed by several authors in the field. The authors use their personal experience to explore obstacles present in parenting through domains such as encouragement, belonging, and shame. In each of these domains, tension points exist when two or more possibilities are seemingly opposed to one another and both have hefty consequences to consider. The authors outline tension points for each domain and offer questions that African American parents may have in regard to overcoming these obstacles. They suggest nuances that traditional Adlerian parenting education may not consider. In conclusion, the authors recommend expanding Adlerian parenting education by incorporating an ecological model using interventions targeting the macro-, meso-, and micro-level.