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Additional research is needed to gain a better understanding of the unique demands faced by field instructors working full time in wilderness-based expeditionary programs. Connections between perceived challenges and consistently high rates of turnover in these employees remain mostly unexplored within outdoor program research. The purpose of this study is to present the findings from a review of literature as well as to indicate areas for future research about challenges facing field instructors employed in wilderness-based expeditionary programs. Findings presented in this paper include, first, what is currently known about this population, second, challenges encountered outside the work context, as they are perceived by these individuals, and finally, potential solutions to address these issues. This research informs future discussions directed towards encouraging front line employee retention in this unique field.