As new assistant principals, our participants spoke of the importance of gaining experience. In this qualitative study, four years later, they admit that professional expertise must be a combination of challenging experiences and honest feedback from mentors. Furthermore, they present that this expertise is contingent upon identity. Transitioning along a career pathway becomes interplay of what the job requires, how the leader adapts when accepting and performing those responsibilities, and a deepening awareness of the congruence between personal and professional identity.