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This discussion of Dr. Pauley’s paper (this issue) on the therapeutics of the fee first highlights the various valuable contributions Pauley makes. It applauds his unusual openness in sharing his internal vulnerability with patients around fees, his raising the question about why fee setting is so complicated for analysts and patients alike, his focusing on omnipotent fantasies in the transference and countertransference, and his uncovering of the multiple meanings money has for therapists beyond just their income. Berger picks up on Pauley’s invitation to therapists to be more curious about their own discomforts with money. Drawing on her own teaching, writing and clinical experience, she adds to Pauley’s more global ideas, stressing instead the more specific meaning of money in each treatment dyad. Among these specifics, Berger highlights the chronic avoidance of teaching about money in analytic institutes. She clarifies some Freudian ideas about how money can become tied up with anal witholding, and offers examples of how she got stuck with three patients around setting and raising their fees. Berger describes how these patients’ believed that their fees could mean safety, value or exploitation and how these attribuitions generated countertransference blind spots for her. The discussion urges clinicians to keep digging hard into themselves for the many meanings of money, to pay attention to the devil in their own details, and thereby maximize the richness of their work with patients around a topic so loaded for all of us.