Up until the resurgence of an academic journal, the field of educational supervision has had to travel incognito (Glanz & Hazi, 2019; Mette, 2019). With the development of the Journal of Educational Supervision, however, supervision scholars have been invited to push new boundaries and experiment with non-traditional approaches about the conceptualization of supervision. In that spirit, I present a mindfulness-based approach to supervision, one that could help supervisors meet the present challenges of remaining more consciously skilled while simultaneously helping teachers practice self-care. While mindfulness-based programs and approaches have taken root in other PK-12 education and higher education fields, supervision remains behind the curve in this area. As such, I use this article to discuss the possibilities of grounding supervision in a more meditative fashion and entertain the concept of the Awakened Supervisor, an exaggerated caricature to demonstrate how mindfulness might be conceptualized. I also address what this might look like in actual practice.