The field of student affairs has been characterized by high levels of attrition, burnout, compassion fatigue, and a lack of appreciation and recognition for its dedicated and highly skilled professionals. The COVID-19 pandemic magnified and intensified these tensions, and a high percentage of student affairs practitioners are considering leaving the field entirely. Using an interpretative phenomenological analysis framework, this study seeks to explore the lived experiences of student affairs professionals on the front line of the student experience at varying professional levels during the COVID-19 pandemic. Findings include the shifting nature of student affairs work, how a sense of powerlessness has impacted practitioner identity and influenced the priorities and goals of professionals in the field, and how impactful leadership and support are on practitioner retention. Recommendations include establishing consistency and transparency in student affairs roles and developing formal reward systems within the field. These recommendations have the potential to guide leaders and human resource officers in cultivating supportive and healthy campus environments that retain and uplift student affairs professionals.