This article draws on qualitative interviews to explore the commonalities, contradictions, and tensions in the identities and lived experiences of 16 highly educated and upwardly mobile Black Canadians who were born and raised in Canada or born in another country and raised in Canada. In contrast to both popular and scholarly discourses that essentialize Black people, the experiences and perceptions of study participants were characterized by polyconsciousness, ambivalence, fluidity, and hybridity. Most reported feeling a simultaneous sense of estrangement and belonging in a Canadian context largely perceived as Eurocentric and White centered. A sense of alienation from Canada led many to embrace their transplanted ethnocultural heritage as well as a transcendent Black racial identity. Despite the protective and empowering function that a Black identity can provide in the context of a society perceived to be racist, most participants shared a complex and conflicted relationship with Blackness. While many embraced essentialist and counterhegemonic constructions of Black identity, they also resisted the discursive constraints of this and other identity categories. Because of their academic and occupational accomplishments along with other factors, participants reported occasionally having to defend or justify their Blackness to racialized peers. Finally, many participants viewed middle-class ideals of success as a vehicle for improving the plight of the Black community as a whole. In this vein, these individuals attempted to use their educational and career success to challenge racial stereotypes, furnish youth with positive role models, and equip Black people to become agents of social change.