The purpose of this study was to explore elementary second-stage teachers’ (4–10 years experience) career decisions and the teaching and working conditions associated with those decisions. Retaining teachers is of extreme importance to public schools because chronic turnover is financially, organizationally, and instructionally costly. The study was conducted in two phases: (1) the collection and analysis of quantitative Teaching Empowering Leading and Learning Massachusetts (TELL Mass) (2014) survey data and (2) the collection and analysis of qualitative findings from interviews and a confidential questionnaire to obtain background and demographic information. Descriptive statistics were used to analyze the survey results. A thematic analysis (Braun & Clarke, 2006) of the interview transcripts was conducted to identify themes. Both school leadership and instructional practices and support proved to be important to survey respondents. However, the responses to the survey did not show that elementary second-stage teachers had markedly different immediate professional plans than their novice and veteran counterparts. Further, according to the survey data, there were no significant differences in the teaching and working conditions that affect the immediate professional plans of novices, second-stage, and veteran teachers. The elementary second-stage teachers interviewed identified the importance of the social aspects of teaching––students, colleagues, and school and district leaders––over any other teaching or working condition, when making career decisions. Even in challenging environments teachers noted how leaders and colleagues can impact decisions positively. These results, while not generalizable, can inform administrators, schools, and districts seeking to decrease elementary second-stage teachers departure from the classroom. Implications for practice and policy and for future research are suggested.