Employees that telework do so for different reasons, including being environmentally responsible, freedom and flexibility, autonomy, and dependent care. However, when the global pandemic COVID-19 hit, the number of teleworking individuals abruptly increased, including but not limited to the education field. There is limited research on how the effects of COVID-19 impacts teleworking. The purpose of this study is to investigate what educators experienced during the pandemic and how it affected their physical and mental well-being. Snowball sampling was used to identify participants that met the specific criteria for the study. The sample respondents included in this research study were licensed educators, certified in a specialized field, that worked full-time (35 hours or more a week) for a K-12 school in a physical setting. These respondents included administrators, counselors, and teachers who transitioned to working and teaching from home when the pandemic started. The semi-structured interviews for this study were conducted using Zoom. The data collected during individual interviews with the participants described the experiences of educators who transitioned to telework due to COVID-19. Transcript accuracy checks were utilized to review and confirm the complete interview transcripts. Data analysis occurred with the use of Dedoose, a qualitative data analysis software. The three emergent themes were: (1) time, (2) boundaries, and (3) well-being. The contextual categories within the themes were: productivity, challenges, flexibility, work-life balance, mental and physical health, value and empowerment, and social isolation. Educators offered recommendations for practice to promote trainings for teleworking, provide clear communication for expectations, consider work-life balance, arrange resources for mental/physical health, provide necessary technology and hardware, and acknowledgement and recognition. The findings from this study could be beneficial for leaders when transitioning to a teleworking structure, giving opportunities to support employees virtually and help establish, implement, and execute teleworking policies and procedures to meet their organization's and employees' needs. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]