As Michael Oakeshott put it: “Cervantes created a character in whom the disaster of each encounter with the world was powerless to impugn it as a self-enactment.”…The quixotic life is not thwarted by a lack of results; its value lies in the experience of freedom that it enacts.  That is why it is possible for the pessimistic ethic to persevere in the most adverse circumstances, when optimism has nothing to offer except an unfounded hope that is little more than wishful thinking.

All narratives, as all lives, must end (”human affairs are not eternal but all tend ever downwards”)–this is the pessimistic knowledge that grounds Cervantes’s perspective.  But if we all face destruction at the hands of time, this need not convince us to resign ourselves prematurely.  Although in one sense, nothing about the world has been changed for the better by Quixote’s actions, his success consists in having led a life consistent with who he is.  Like Sisyphus with his stone, he has achieved dignity by accomplishing nothing.  Or rather, what he has accomplished is to have enacted the value of pessimism in the form of a quest.  He has made his life unpredictable, memorable,and narrativisable by bringing his life-practice into contact with the world.  And a small portion of the world responds by allowing itself to be inspired by this practice. ~Joshua Foa Dienstag, Pessimism: Philosophy, Ethic, Spirit

One of the best parts in Dienstag’s book is his chapter on Cervantes and Don Quixote, a work referenced by many of the major pessimists Dienstag studies.  In his telling, Dienstag mentions Quixote’s habit not of recounting specific teachings or codes of the knights-errant whom he is imitating, but instead tells stories.  That is perhaps what separates every truly humane person from an ideological one: the love of stories and the telling of stories to provide examples to follow, rather than programmatically reciting propositions, testing for ideological purity and uttering banal platitudes about the betterment of the world. 

Every story has an end, and many endings are not happy, but the good endings have a certain integrity and dignity of an authentic life.  Meanwhile the wheel of alleged Progress grinds ever onward, like time, like the grindstones of the windmills in Don Quixote, never satisfying, never satisfied, always consuming and offering us little in exchange for what it extracts from our humanity.  The optimist tries to cheat time, to beat it at its own game through every scheme of improvement imaginable, whereas the pessimist takes time on its own terms, gets knocked off his horse and badly bruised, but shakes off what has happened and goes on to the next adventure. 

The optimist would have the world be other than it is, and would have man become something other than what he is.  Pessimists and, I believe, Christians both seek for man to become what he is, though obviously the pessimists deny the Christians’ means of realising this and Christians typically reject the pessimistic rejection of all transcendence.  But what both tell us is that man can be transformed into who he truly is, made new, which is different from the optimistic view that man must inevitably keep becoming better and better in an unavoidable parade of unfreedom.  People who tell us that history has a direction steal from us the freedom that is “gained when one’s existence is detached from the narrative of progress.” (Dienstag, p. 198).   

Optimists insist that reality is insufficient and that they will redress the imbalance; they want us and everyone in the world to become someone else.  But as Ortega y Gasset said, “A hero, I have said, is one who wants to be himself…Don Quixote…is a hero.”  Let us, then, tilt at windmills in the understanding that the only true despair, the most bitter illusion, is the expectation of making the world fundamentally different from what it really is and the hope of lasting victory in this world.

As Dienstag says elsewhere:

Though the reader may reflexively think of Don Quixote as an inveterate optimist, charging at windmills and the like, I would suggest that this has more to do with the popularity of the musical Man of La Mancha than with Cervantes’s actual text.  Whatever the merits this lachrymose bit of theater may possess, fidelity to the spirit of Don Quixote is not actually one of them.  If anything, Man of La Mancha resembles the heavy-handed, Wagnerian operatic romanticism that Nietzsche so feared being associated with….As Nietzsche reminds us, however, Cervantes’s book was received by its readers as a bright comedy and was, indeed, internationally successful on that basis.  While we cannot read too much into this success, I want to at least suggest that the popularity and influence of Don Quixote are at least an interesting piece of evidence against the oft-repeated canard that pessimism must somehow be an elite or minority perspective.