This autoethnography tells my story as a French American woman who lives in the United States and worked with hundreds of school leaders in five African countries over a period of six years. Using a cultural proficiency continuum, I illustrate my learning and changing frames of references pertaining to cultural differences. Movement along the continuum indicates an alteration in thinking that progresses from marginalization to inclusivity. My experiences, mistakes, and lessons learned contribute to the discourse on cultural difference. For six years, I spent more time on the African continent than in my American home. These extended stays allowed me to observe and alter my understandings of cultural values related to colonization generational trauma, the notion of personal space, community, verbal and non-verbal communication, and the importance of culturally relevant leadership and teaching in order to serve refugee and immigrant students across the globe. It is my hope that this autoethnography will encourage school leaders across the world to adopt an empathetic mindset towards students and families coming from different cultures. Taking into account culture is crucial as schools in the United States are becoming more and more diverse racially, ethnically, and linguistically.