Supervisees who have experienced disturbing therapeutic incidents that undermined their professional self-experiences need a supervisory environment of sameness and solidarity to process and learn from these lived experiences. To create such an environment, supervisors need to minimize the sense of safety asymmetry between themselves and their supervisees by awakening to the ‘dark,’ ominous truths of professional life. This process is facilitated by summoning memories of therapeutic experiences of failure, vulnerability and frustration at having insufficient time to achieve wished-for therapeutic goals. Awakening to these truths inspires a dark experiential mode that helps the supervisor share the supervisee’s destiny and existential anxiety. Despite the contradiction between the dark and the playful, experiential modes, both are essential for creatively understanding the supervisee’s disturbing therapeutic experiences and learning from them. Moreover, when these modes are interwoven, they enrich and strengthen the supervisory process by diversifying the supervisory dyad’s ways of perceiving the unfolding therapeutic interaction and of coping with supervisory challenges.