It boils down to a question of where a generation of educated, privileged, creative class sorts of people are ending up. As a group, those who wind up being hipsters tend to have a good deal of opportunity, so if hipsterism is a kind of psychological/cultural zombie state (suggested by the Time Out New York article, and the Adbusters article from a couple years ago “Hipsters: The Dead End of Western Civilization”) then there is a vast amount of potential being wasted.I think that's partly right: People are aware of this negative possibility of becoming a hipster, and it's important to figure out what cultural forces conjure that possibility and make it such a powerful and pervasive archetype. I don't think hipsters constitute a lost generation of young people who were distracted from some important cultural work by skinny jeans and Animal Collective, though. Instead, I think there may be something more pernicious in how the category is feared, how the threat of the label may be brandished to stifle creativity. (Which I suppose makes some want to seize the mantle in a radical act of reappropriation, the way the term queer was salvaged by academics and activists.)
"Hipsterism," as I tried to argue in this post, is more a fear of irrelevance or phoniness than it is an aesthetic one would purposely adopt. It is the shadow that passes over us when we begin to tentatively plan to do something unconventional, the chill that tells us that maybe it would be safer to do nothing rather than become one of them, trying for cool but failing. That is to say, "hipsterism" is the term for that sinking feeling that cool is at stake in any endeavor, and that nothing can be pursued for its own sake anymore. Of course that is not true, but it often feels like it is, and the image of a stereotype arriviste hipster is there to personify that feeling. And the final twist is that once we begin to fear becoming hipsters, begin thinking primarily about the way what we are doing will be perceived by others who somehow can see through us to the roots of our motivations, we become at that very moment hipsters ourselves.
To prompt us to that moment of self-consciousness are those people who intently make a business of cool -- whether they are hunting for it or selling it to others or trying to associate it with products or whatever. These people, less hipsters than youth-culture entrepreneurs, see the insecurity that cool generates as a profit opportunity, and they try to persuade us (and perhaps themselves) that the preoccupation with cool is actually a healthy interest in style and novelty, enriching our lives with creative possibility. This group, a subset of the so-called creative class, is not itself made up of a bunch of hipsters, but the hipster is their invention, I think. If we need a cultural enemy, these are the people. These are the collaborators, the infiltrators, the saboteurs that complete the circuit between subcultures and corporations, subverting the original aims and intentions of a group and orienting it toward straightforward financial opportunities.
But Lind is probably right that in time (sooner than we think, I expect), hipster will be just like hippie or beatnik, a word that conjures a stereotype of an era, a moribund caricature pickled in history and no longer threatening. Meanwhile, the shadowy quality of infiltration and appropriation the hipster once represented will have moved on to be embodied by some new au courant imago.
Perhaps because I'm reading Daniel Bell right now, but I wonder whether the revulsion at the idea of hipsters is an important component of the dialectic that pushes people who begin in the cultural left in a conservative direction. In The Cultural Contradictions of Capitalism, Bell fulminates about the self-centered relativists, hedonists, and "antinomians" of the 1960s who took over capitalist culture and destroyed the work ethic and religious piety. Bell wants to see limits set on "cultural experiences which go beyond moral norms," wants society to "recognize the demonic in the delusion that all experience is 'creative.' " The fixation on preventing hipsters from destroying authenticity would seem to recur to Bell's idea of fixing a more or less arbitrary limit on culture. In capitalist society, a hipster figure will always be generated by the way commercialization is necessary for cultural legitimization (commercial viability has replaced religious sanction in this respect). The received idea of the hipster proves that a given cultural phenomenon has become integrated in commercial society, is reliably exploitable, has no actual subversive potential, is just an insubstantial matter of style.