This paper explores the experiences of practicing bilingual (English/Spanish, English/Portuguese, and English/Haitian Creole) and English as a Second Language teachers after completing a Bilingual Bicultural Education Certification program. It highlights how teachers defined success when working with their emergent bilingual students and names the barriers that teachers identified as preventing them from success. Using a Systems Theory for Career Development framework, analysis indicated that, from teachers' perspectives, elements that contributed to success were often framed as the result of interpersonal and social factors while major barriers to success were often described as resulting from environmental and, to a lesser degree, social factors. Implications for teacher education and professional development are provided.