In this qualitative study, we examined the perspectives of four urban K-12 principals on what hinders and helps their vitality. Grounded in 60 minute interviews, 10 monthly, full-day observations, and document analysis with each participant, we identified three themes hindering their vitality: (a) illusion of control of productivity strategies and order mind-sets, (b) unsustainable nature of the career, and (c) adult management. In terms of helping vitality, we identified three themes: (a) time on priorities, (b) relationships with students, colleagues, and peers, and (c) sense of renewal and hope. Implications for theory and practice are included.