Progress in psychoanalytic work can seem slow and arduous. Patients noticing this may harbor inner questions and doubts as to how and when—and even whether—they will finally “get better.” After examining the status of the related concept of “repetition compulsion,” this article explores such concerns by enumerating certain heretofore underappreciated barriers to psychic change; it also discusses various potential—but currently undersung—facilitators of such change. To help illustrate these factors, a case example is presented of someone struggling with a micro-traumatic pattern that might be called “subservient caretaking.” In this maladaptive dynamic, the individual (often the male in the context of heterosexual couples) behaves in an overly nurturing, self-abnegating way toward his partner (often, female), who he perceives as weak and therefore needing this kind of “patronage.” The relevant obstacles and potential aids to overcoming this sort of deeply ingrained pattern are explored in relation to the case example offered.