Approximately half of a million educators move or leave the profession each year with an estimated 41% of all educators exiting within the first five years. Additionally, agriculture teacher preparation programs are not producing enough graduates to meet current demands with 1,476 agricultural teacher vacancies existing in 2016 and only 772 individuals completing an approved teacher preparation program to become fully licensed. While the lack of young people entering the teaching profession is concerning, researchers have suggested teacher attrition is the predominant reason behind the ongoing teacher shortage. The purpose of this qualitative study was to identify factors influencing former agriculture teachers’ decision to leave the classroom. Themes developed that stem from unrealized expectations for one’s career and the belief that being an excellent agriculture teacher is incompatible with a satisfying personal life. A final theme indicated the need for additional support alongside a philosophical shift in the profession that dictates “more is not always better.” Recommendations are made for further research along with ideological and practical shifts needed within the profession to improve teacher retention.