For as long as I've been in digital media, skeuomorphs have annoyed me.
The original CD ROMs, for example, often had a home screen that started with a bookshelf, and you clicked on the 'book' you wanted to 'open' (excessive use of quotations intentional). Here's the thing: bookshelves are a great idea if you want to store actual books on an actual shelf. They're a silly way to index digital information, though.
If you haven't guessed, a skeuomorph is a design element from an old thing, added to a new one. I think that printing a cork-colored filter on a cigarette that no longer has cork involved is just fine. But when skeuomorphs get in the way of how we actually use something or build something, they demonstrate a lack of imagination or even cowardice on the part of the designer. (Sooner or later, just about everything, even the alphabet I am writing with, could be considered skeuomorphic... my point is that embracing the convenient at the expense of the effective is where the failure happens).
Craig Mod writes eloquently about this, which reminded me of some of what we did with the covers for the books from the Domino Project more than a year ago. We can take this thinking even further, though.
If a company is organizing to create music on MP3 or ebooks, it makes no sense to steal the organization of the past labels and publishers. High unit pricing, copy protection, significant advances, big launch parties and royalties all make much less sense when the fundamental rules of the product itself have changed. So do things like office buildings and layers of vice presidents.
Yes, the brain is organized by analogy. Analogy is the key to understanding. But, no, the analogy doesn't have to hit us over the head. The more obvious the analogy, the less effort the creator has put into telling us his story.
When it's cheaper to ship, then risks are lower and you don't need to staff up to avoid mistakes. This means you can take more risks, be less obvious and abandon what feels safe for what is safe.
This consistency of structure is the single biggest reason that motivated market leaders (in any industry) fail to transition to new paradigms--they insist on skeuomorphic business models, bringing along the stuff that got them this far, even when it's unnecessary. This is why Conde Nast is doomed, even as the population spends more (not less) time consuming media.
Yes, it's far easier to get understanding or buy in quickly (from investors, in-laws and users) when you take the shortcut of making your digital thing look and work just like the trusted and proven non-digital thing. But over and over again, we see that the winner doesn't look at all like the old thing. eBay doesn't look like Sotheby's. Amazon doesn't look like a bookstore. The funding for AirBnB doesn't look like what it took to get Marriott off the ground...
The only reason to venture into the land of the new is to benefit from the leap that comes when you get it right. So leap. (Well, it's not actually a leap, that's an analogy.)