This manuscript highlights the experiences of three urban teacher-residents (current and alumni) as they chronicle their journeys finding their way into their role as teachers, supporting learners through a teacher cadet program, developing through a year-long teacher residency, and then moving into their first years of teaching in the urban schools of their community. These PDS "boundary spanners" have developed simultaneously within both the public school and university spaces allowing them to provide meaningful implications for PDS partnerships and for recruitment, development, and retention of teachers.