In this chapter, the author describes the feelings of hopelessness within the analyst. This often unspoken experience can cause disruptions in the analyst's ability to empathize with and deepen the analytic experience for the patient. The experience of hopelessness is a frequent visitor to the analytic setting. Sigmund Freud's referring to psychoanalysis as an "impossible profession" became commonplace over time and took some of the sting out of this remarkable aspect of our clinical work. With this caution in mind, acute experiences of hopelessness in the analyst can be valuable guides in uncovering previously unfelt conflicts and fantasies. The acute experience of hopelessness in the analyst can also serve as a signal for the possibility of unfelt loss and mourning on the part of the patient. The chronic hopeless countertransference, although difficult to bear, becomes a valuable tool in understanding the patient's inner conflicts and resistances.