There are moments of teaching in every educator’s life when you are reminded that you are not the smartest person in the room. Rather, the students around you have much to teach you. This can be as much the experience for those teaching young children as those who teach adults or at universities. Such moments can change us forever. Such an approach to education draws on the work of Paulo Freire’s (1970) vision of a pedagogy that is rooted in the lived experience of our students. The argument is that our role as educators is to highlight power structures that shape these experiences, inspiring students to question, challenge, and agitate for change. Freire believed that education was about addressing the needs of the world and connecting with the problems surrounding us. This chapter discusses the cultural interactions from this perspective and outlines how this can alter our life journey. Drawing on the concept of ‘cultural humility,’ I argue that this should be seen as a step beyond cultural competence. Cultural humility is a guiding principle for educators seeking to facilitate culturally appropriate learning and as an effective approach for ethical and sensitive communication in diverse and constantly evolving learning and professional settings.