I think that a kind of cynicism is dangerous, but so is its opposite, being unquestioning, undoubting. You want to be somewhere in the middle

The distinctive aspect, in comparison to verbal irony, is that this 'irony sensu eminentiori [in the eminent sense] is directed not against this or that particular existing entity [...]'

[...] To illustrate that A Heartbreaking Work of Staggering Genius is 'truly a work from "the Age of Irony", Korthals mentions that the work is 'full of postmodern games with typography, expanding footnotes et cetera', and asks, rhetorically: 'How post-ironic can an author with such a media-conscious and self-conscious main character be?' However, the elements that Korthals mentions (further on, she also adds 'polyphony' and 'ambiguity') are not necessarily even expressions of verbal irony (compare the aforementioned pop references in Wallace); they might just as well be regarded--perhaps even more plausibly--as normal aspects of the portrayal of contemporary reality. Above all, the mere presence of these elements in the book, even as potential verbal ironies, does not automatically undercut its critique of existential irony. Also, how could one then ever critique contemporary reality, if just describing that reality would by definition imply ironizing one's critique of it?

It is important to note that irony is a purely negative movement: it destroys what is given, thereby liberating the individual, but it does not contribute anything to the formulation of the new, to the content of the individual's self-becoming. Therefore, the freedom that arises from this break with immediacy, is a negative freedom: a freedom-from. Kierkegaard writes that in irony, 'the subject is negatively free, since the actuality that is supposed to give the subject content is not there. He is free from the constraint in which the given actuality holds the subject, but he is negatively free and as such is suspended, became there is nothing that holds him'.

Kierkegaard calls this form of irony, Socratic. According to Kierkegaard, existential irony came into the world with Socrates. Socrates used irony to topple the immediate actuality of his time, which to him had lost its validity. For Kierkegaard, the liberation that Socrates brings about, is the essential stepping stone towards a personal moral interpretation of one's existence. The negative freedom that it brings about is a necessary condition for the subsequent formulation of a positive freedom (a freedom-to), in which one gives actual content (positivity) to one's freedom and establishes one's self-chosen moral framework. However, because irony is pure negation, it cannot be the source of that positivity. Consequently, Kierkegaard concludes that irony should only be employed temporarily, and that subsequently one should start to give positive meaning to one's freedom.

In A Heartbreaking Work of Staggering Genius the critique of the ironic attitude is most evident in the passages concerning Might Magazine. As mentioned in the previous section, the book offers a positive portrayal of the original (however vague) ambitions of the magazine. But soon these ambitions are lost to an attitude of total negative irony:

We begin a pattern of almost immediate opinion-reversal and self-devouring. Whatever the prevailing thinking, especially our own, we contradict it. We change our minds about Wendy Kopp, the young go-getter we heralded in the first issue, and her much-celebrated Teach for America. [...] in a 6,000-word piece that dominates the second issue, we fault the nonprofit for attempting to solve inner-city problems, largely black problems, with white upper-middle-class college-educated solutions. 'Paternalistic condescension,' we say. 'Enlightened self interest,' we sigh.

This passage summarizes the ironic-aesthetic attitude of the editorial staff of Might: every position, every idea has a flip side that can and thus has to be exposed. Timmer writes: 'They are so accustomed to a negative dialectic or a deconstructive attitude that they are much better at articulating what they do not want than they are at formulating any constructive goals and visions.' Initially, this 'deconstructive' activity might even seem like a viable and worthwhile activity in itself. But, as becomes clear from their choice of targeting vulnerable, idealistic initiative, the editors' irony serves, above all, to liberate them from commitment to any of these positions, and insulates them from any criticism that might be brought against them. For Might's editors, the ironic stance of 'immediate opinion-reversal'--that is, to he `positionless'--seems to be the only viable, safe attitude.

However, in the course of the book the editorial staff grow more and more frustrated with their own endless irony. The emptiness of the aesthetic attitude starts to dawn on them; their work becomes 'depressing, routine': 'We debunk the idea of college in general, and marriage, and makeup, and the Grateful Dead - it is our job to point out all this artifice, everywhere.' In the end, Might Magazine loses out to general frustration. The editorial staff realize that their ironic efforts have led to nothing. They have exposed falsity and artificiality everywhere, but have offered no alternatives. As Timmer observes: 'Might, in that sense, implodes. It implodes because their critical stance is deconstructive and eventually turns inwards.' In the end, the editors stand empty-handed: 'all these hundreds of thousands of hours, were going to end without our having saved anyone [. . .]--what had it all been? It had been something to do, some small, small point to make, and the point was made, in a small way'.

According to Judge William, the aesthete laughs the 'laughter of despair' and Kierkegaard speaks of the 'superior indolence that cares for nothing at all, that does not care to work [...], that disperses and exhausts all the powers of the soul in soft enjoyment, and lets consciousness itself evaporate into a loathsome gloaming'.