This literature review aims at exploring two career theories, one career model, and their applications to facilitate the comparison of their advantages and shortcomings in understanding contextual and personal factors influencing teachers' career choices. It first examines the chosen career theories and models in teachers' professional development, namely, Fuller's Concern Stage Theory, Fessler's Eight-stage Teacher Career Cycle Model The Social Cognitive Career Theory. Common factors encapsulated by those theories are outlined, and a close examination of how those theories prioritize contextual and personal factors are also discussed. This literature review also highlights some current research gaps of examining teachers' their career choices: an ambiguous interplay between personal and environmental factors, an ambivalent attitude towards considering psychological factors, neglecting in-service teachers in late-career development and exit stage, inadequate synchronic and diachronic studies on contextual and personal factors, and a weak association between influencing factors, teachers' sense of identity and their career choices. Through a discussion of those teachers' career theories, models and their applications, this literature review probes into the importance of examining the interplay between personal and environmental factors in order to understand how and why experienced teachers become demotivated and frustrated in different career stages. It also provides a more holistic view and insight on retaining experienced in-service teachers and alleviating the global teacher attrition and shortage problem.