In this phenomenological study, Latino/a secondary principals from suburban school districts were interviewed regarding their career advancement experiences. Participants described various motivators (drivers) and barriers experienced throughout their principal careers in suburban schools. Data were analyzed and interpreted using Moustakas’s (1994) phenomenological reduction approach and framed by Lewin’s (1954) force-field analysis theory. Internal drivers included: passion for educational leadership and drive and determination. External drivers comprised family support and mentoring. Internal barriers were career doubt and questioning of own leadership capacities. External barriers comprised gender bias and district level resistance to Latino/a diversity in hiring. Implications for the recruitment and retention of Latino/a principals in suburban school districts, as well as principal leadership preparation programs are discussed.