The effects of mental health challenges in the United States are growing and affect both Grades P-12 special education teachers and faculty at institutions of higher education (IHE). Educators struggle with compassion fatigue and associated burnout. With educators leaving the field for a plethora of reasons, it is vital to examine factors that support those who remain in education. Thus, we analyzed factors that support the retention of educators at both levels of instruction. In a qualitative analysis of data from survey respondents (N = 200), we examined the resiliency and endurance of practicing rural P-12 special educators and faculty at IHEs. Results from inductive content analysis indicate that factors leading to persistence in education begin with educators finding meaning in their teaching. Educators who demonstrate career endurance have a strong sense of self-efficacy in their teaching abilities, receive emotional benefits from their students, and have quality opportunities to mentor and collaborate with others. By contrast, some educators indicate burnout is a key factor for leaving the field, and reported reasons include low pay, paperwork, poor work/life balance, lack of respect, and the mental health of themselves and their students. Based on these findings, we offer recommendations for research and practice.