There is a fine line between the confessor and the jester. Each provides outlet, perspective and opportunity: variously, to short-circuit situations, buy time for consideration and provide an outlet for emotion. Intense practice needs intense and focussed reflection if professionals are to sustain longevity and find flourishing. In the light of curious encounters, particularly the tales of Alice, the similarities and differences between the roles of confessor, jester and supervisor are noted. The particularity of the supervisor as a practitioner with expansive engagement is affirmed as appropriate for contemporary supervisory practice in leadership and the caring professions.