During the COVID-19 pandemic, schools and post-secondary institutions announced their closure and faculty were required to shift immediately to remote delivery of classes. The impacts of this transition were emotionally, physically, and mentally taxing for learners and educators; however, much less attention has been paid to faculty. The current qualitative study aimed to explore the pandemic’s mental health and well-being effects on educators belonging to a Canadian undergraduate University. Fifteen instructors consented to be interviewed, and they were asked to share one or two moments in each a high, low, and turning point during their time teaching through the pandemic. Instructors reflected on the transition to remote teaching; increased workload; lack of healthy work-life balance; managing a virtual learning space; changes to and management of student, colleague, and personal relationships; negative impacts on mental health; safety concerns upon returning to face-to-face instruction; and self-care practices to safeguard their well-being.