This research examined the language used by higher education development professionals, specifically similar and dissimilar tropes and how they shape the perception of those development professionals. By studying these linguistic devices, insight is provided into this particular occupation and the effects these devices have on perceptions and interpretation. The findings in this study could help to produce more skilled communicators in the field and could be used as a framework to study other professional positions. Semi-structured interviews were conducted to gather data from twelve participants, and the data was then analyzed through thematic analysis. Findings revealed the types of metaphors used by higher education fundraisers and if and how they shaped their perceptions of the profession. Findings also showed what contradictions, paradoxes, and ironies are found in the field and if and how they shaped perceptions of the profession. This study applies theoretical aspects of organizational communication to the field of higher education development presenting new data. This study also provides practical implications for those currently in the field to consider.