Around halfway through I jotted down a few thoughts. I like and appreciate people thinking about this sort of thing however, so I'm not saying any of this to offend.
> I don't see any reason that we couldn't be storing our files in abstract squares rather than folders in the sky.
...because they're called folders, and we know how to use them? If I said, "Here, have a square," is your first instinct really to think oh! that must be for putting stuff in/on? Sure, you can abstract them to just a symbol but it's unnecessary. It's not like the system cares what you call it or how you choose to display it.
> The world's most advanced phones include an icon that looks like a phone handset that you haven't touched in 20 years, unless you've used a pay phone recently.
I have in fact, but that's not the point. Again, we know the shape. There aren't many things it could be besides a phone. You could show someone a glossy brick I guess, but what good would that do? The best alternative I can think of would be something like a speaker or microphone, but where's the argument that that would actually be better?
> At some time in the past the magnifying glass became the "search everywhere" icon, but for some reason binoculars are for searching within a document.
I'm just now realizing that he must be thinking of a specific piece of software. I gathered he was on Windows, now I see he worked at MS. Is this Office? This one I agree with, but it sounds like a quirky error made by some engineer or perhaps phony UX consultant. Same goes for the clipboard– hell if I know why MS would use that icon for paste, but in no other software that I can think of is that normal.
> Envelopes
Same thing as folders. So our terminology expanded to cover abstract digital entities, but that doesn't make it a hinderance to our intuition. Folders, packages, envelopes... maybe they're too nostalgic for the bold futurist, but generally it's about as practical as you can get.
> Wrenches and Gears
Who hasn't used a screwdriver? Or never seen a wrench? Even the people who don't own one probably know what it is. I'm indifferent to the gears/tools thing. It still makes sense, but I'm open to new ideas– preferably a little more clever than a circuitboard.
> Microphones
For speech recognition, would an ear be better? I think most people would get the microphone bit simply from watching cartoons, talkshows, album covers etc... but I admit this will likely be more foreign in the future, and is already disconnected from people in developing countries without that much media exposure (although they apparently have an iPhone/Pad/Pod).
> Photography
It's kitsch. It still makes sense because the alternative to a square with a border is a square without a border. But for all of us who still use medium/large format cameras from time to time or for work, we can simply pretend. Lenses are a-OK.
> Televisions
Actually, for the large number of people who gave up cable for hulu and netflix but still want to catch the news– yes! I do have rabbit ears! Maybe it's a little too retro for most video icons, but again– it till makes sense, it just may be better suited to apps that show live broadcasts.
> Carbon Copies and Blueprints
Eh, so the term's (carbon copy) a bit outdated. But then again, when was the last time I "pasted" a document together? Yeah, Drawing I. As for blueprints... it makes sense for XCode right? And CAD. We may not use blueprints so often anymore, but it's less ambiguous than "construction documents," which might as well be "layouts". Which might as well be squares with a shape on them. Etc...
Basically, this would be a far more interesting post if the author would go further into making actual suggestions. Some of it makes sense because it's intuitive, some of it makes sense because we're used to it. If you want to correct the latter, you've got to show something what's better.
Edit: ouch, that's an ugly post. Not sure if I can format it in any way.
Also, I'm looking forward to seeing what people suggest in the discussion here. It's an interesting topic for sure (and I'm sure there will be plenty of people to disagree with me).