Through the defining power of words, the phrase “difficult-to-reach” patient reflects the extent to which the analyst inverts the patient's will to change and makes the analyst the subjective agent of treatment progress. If making a constructive contribution to another person's life engenders a sense of creative agency, the traditional dichotomies of analyst/helper who gives and an empty patient who receives may not be useful. I trace the evolution of a 23-year-long psychotherapy from a parent–child dynamic through to more uncertain relational terrain in order to illustrate how the analyst's own evolution may have clashed with the patient's ambivalence toward change and endings. I raise questions of how the dignity of making a creative contribution to the “reachable enough” analyst's life may enable the patient to work through gratitude, attain a sense of belonging, and terminate with good conscience.