This basic qualitative study was part of a larger research project and specifically explored the experiences of 10 seasoned student affairs professionals from four-year universities who overcame obstacles associated with COVID-19. Participants in this study contemplated leaving student affairs due to poor job factors, feeling devalued, stressful decisions regarding personnel, and the added pressure of building their pandemic response plan as it unfolded. Despite these considerations, this study found that nearly all participants exhibited gritty behaviors (e.g., passion and perseverance) that motivated their persistence in the field. This study also identified trends that future student affairs leaders should consider addressing when planning for the longevity of the student affairs workforce. These considerations include aligning workplace and workforce expectations and setting realistic expectations between employees and organizations when it comes to organizational decision-making.