The author reflects on his three decades as a street interculturalist. He begins by relating how he stumbled across interculturalism at a 1991 educational conference, proceeded to become a Summer Institute for Intercultural Communication faculty member, and served as the Creative/Cultural Advisor of the award-winning television series, “Dora the Explorer” and “Go, Diego, Go!” He then relates how interculturalism helped him develop greater insight into his growing up in a multiethnic, bi-religious, and tri-lingual home, leading to the publication of his 2012 memoir, Rose Hill: An Intermarriage Before Its Time, and his widespread performing of his one-person autobiographical play. He concludes by examining how intercultural thinking continues to influence his varied professional endeavors.