For example, Berlin famously claimed that to conceptualize liberty simply as the ability to do what one wishes is problematic. Sarcastically, Berlin pointed out: „[I]f I find that I am able to do little or nothing of what I wish, I need only contract or extinguish my wishes, and I am made free”. Despots of all stripes have sought to mold people’s desires to whatever form of life they have invented for them, such that in a perverted sense, the new regime would in effect be „liberating” them. To put it in terms of the slogan Berlin made famous, these regimes would be curtailing people’s negative freedom but with the alleged goal of expanding their positive freedom. Perceptively, Berlin pointed out that
„the doctrine that maintains that what I cannot have I must teach myself not to desire, that a desire eliminated, or successfully resisted, is as good as a desire satisfied, is a sublime, but, it seems to me, unmistakable, form of the doctrine of sour grapes: what I cannot be sure of, I cannot truly want”.
Liberty Berlin thus understandably insisted, has to be more complicated than this:
„[A]scetic self-denial may be a source of integrity or serenity and spiritual strength, but is it difficult to see how it can be called an enlargement of liberty. If I save myself from an adversary by retreating indoors and locking every entrance and exit, I may remain freer than if I had been captured by him, but am I freer than if I had defeated or captured him?”
Berlin surely goes too far when he agrees with Schopenhauer in that „total liberation … is conferred only by death” or when he claims that „the logical culmination of the process of destroying everything through which I can possibly be wounded is suicide”. Death can be seen as freer than life only in the sense in which a nonworking watch is more accurate than one that slows down a second per day. And that is not quite the sense of liberty that even the most simpleminded political philosophers have ever had in mind. The stipulation that we can only speak about liberty in connection to beings capable of making choices (or the stipulation that we can only apply the concept of accuracy in connection to minimally working watches) should obviously be admitted. Still, the force of Berlin’s overall point remains strong: a life devoted to avoiding having unfulfilled desires can take the path of drastically reducing our desires, to the point of not resembling a human life. That is a path of uninspiring passivity.
(Rethinking Punishment, Cambridge University Press, 2018, la p. 82)