Boredom has dominated discussions about longevity thanks to Bernard Williams’s influential “The Makropulos Case.” I reveal the presence in that paper of a neglected, additional problem for the long-lived person, namely alienation in the face of unwanted change. Williams gestures towards this problem but does not pursue it. I flesh it out on his behalf, connecting it to what I call the ‘curmudgeonly attitude to change.’ This attitude manifests itself in the tendency, amongst those getting on in years, to observe that things are getting worse. Curmudgeonliness is typically met with dismissal because it often concerns changes that don’t radically inhibit the curmudgeon’s well-being or autonomy. I believe that taking the curmudgeonly attitude more seriously will provide insight into the longer-lived self and its relation to the future. Using Williams’s approach to longevity as the framework, I contend that—as with boredom—a sense of alienation born of curmudgeonliness can become terminal for the subject, rendering her unable to envision the future as a site of worthwhile activity. However, I also uncover ways in which this agential stasis is significantly distinct from boredom and constitutes a different worry and a different risk for the long-lived individual.