In this essay I discuss my early career as a failed philosophical practitioner when the field of philosophical counseling was still in its infancy. I describe setting up a private practice and discuss various details from my field notes with regards to some of the earliest clients I received. I further depict experimenting with philosophical group therapy in an inpatient psychiatric unit of a general hospital, which by all objective standards turned out to be a disaster. Musings on how philosophy (...) may be successfully applied in the consulting room is considered through a phenomenological-existential approach to therapy. (shrink)