With efforts being made at the national, state and local levels, through legislative and executive means, to address the teacher labor shortage, why is the shortage so persistent? Many scholars attribute the teacher shortage to a “wages alone” argument. Through research and investigation, it is apparent that other factors (which have been largely excluded from the policy conversation) could have a larger impact on ameliorating the shortage. To obtain first-hand data, and field perspectives, teachers were interviewed about working conditions and overall experience. The interview transcripts were examined qualitatively and quantitatively: the transcripts were analyzed using a natural language processing algorithm to conduct a sentiment analysis, which revealed deeper themes across interviews. Transcripts were also assessed by hand to highlight quotes and thematic contradictions. To complement ethnographic interview field work, the teacher shortage policy recommendations by the NJ Task Force were analyzed through a case study framework; this served as a bridge between vague recommendations and implementable action steps for districts to employ. The case study school was selected by balancing 5 core variables and 5 covariates, to be as representative as possible of public elementary schools in NJ. The overall findings highlight how retention and mentorship initiatives are an untapped potential for policy makers, that teachers report high levels of loneliness not captured by many metrics for measuring workplace effectiveness, the need for specific recommendations rather than broad suggestions, and the importance of speaking with teachers as an information source, rather than excluding them from policy making.