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This study examines how 50 current and former urban educators make sense of their identities and how those understandings inform their practice and career decisions. Interviews, conducted in the summer of 2020, revealed that participants’ (intersectional) identities were salient to their motivations for teaching, unexpected challenges and opportunities in building relationships with students, perceptions of teaching and other roles, and their career decisions. The dual pandemics of covid-19 and systemic racism spurred some participants’ critical reflections on their teaching practices and sensemaking about their current or future career paths. By centering teachers’ and former teachers’ perspectives on their own careers and intersectional identities, this study aligns with this year’s theme of conducting humanizing, opportunity-centered, and impactful research.