This article will provide an overview of the impact of the coronavirus disease 2019, also known as COVID-19, pandemic on educators. The transition from face-to-face to online instruction revolutionized perspectives on synchronous and asynchronous course modalities. New live media methods of interaction were adopted with little to no training for teachers and students. Simultaneously, educators, counselors, students, and families faced a multitude of challenges occurring in their own lives and those of their students. These challenges included but were not limited to anxiety and depression, low self-efficacy, fear, domestic violence, substance abuse, oppression, and trauma (Bozkurt & Sharma, 2020; Dorn et al., 2020). The conversion to online instruction during periods of governmental lockdowns, particularly in large cities with high population density, greatly obstructed lifestyles, expectations, and self-care routines for individuals across age groups and socioeconomic levels. While many dramatic changes were occurring due to a healthcare crisis, teachers, counselors, and administrators were troubleshooting student difficulties while working from home and often with limited resources and support (Stone, 2020). The article documents the realities of educating students during a pandemic and the changes that may impact education indefinitely, as well as lessons learned regarding the importance of collaboration, flexibility, and self-care.