The New York Times' David Carr wrote something that made me really sit up and take notice this morning, and for so many reasons that it's actually kind of hard to explain.

First, the basic premise of his article, which I agree with totally, is that Google's Web applications have taken hold with a certain audience because they're so simple:

Not long ago, someone invited me out to the Googleplex, the nickname for Google’s headquarters in Mountain View, Calif.

The fact is, I already live there. And it’s starting to worry me.

My increasingly exclusive relationship with Google started with search, of course, when I switched from Yahoo years ago. Eventually I accepted an invitation to Gmail, with its oodles of storage and very granular search function, and it has oddly become my default database — deep, rich and personal … I added the company’s calendar because I needed one I could share both inside and outside of work. And then the calendar and e-mail started talking to each other — and to me, I guess — by asking whether I wanted to schedule an event that was mentioned in an incoming message. Although it sort of creeped me out, the answer was yes, which it almost always is when it comes to Google.

[And so on. You get the idea.]

“The most powerful form of advertising is to be exceptional,” said Ranjit Mathoda, an investor and technologist who blogs at Mathoda.com. “Google has created an ecosystem that perpetuates itself by being useful.”

With Google, it is always simple, and any engineer will tell you that simple is hard.

If Google owns me, it’s probably because I am in favor of what works.

OK. This is all very obvious, right? Google’s Web applications are simple—they are—and a certain audience out there really appreciates that. One might argue that this approach—simplicity instead of an over-abundance of functionality—is also a big part of what is driving Apple’s successes right now. Many people prefer things that just work, even if the span of what’s possible is less vast than with competing solutions. Windows, by comparison, is arguably a bit much. It does more (yes, I know people with argue with that, but this isn’t really the point of this post) but does so with a more unwieldy interface.

So.

Since this is Google we’re talking about and Microsoft is about 3/5 of the way through releasing its Windows Live Wave 3 services and applications, it’s hard not to draw some parallels here. After all, Microsoft is in the midst of doing what Microsoft does: It’s releasing a massive platform. There are an unprecedented number of new and updated services (see my preview). And there is an entire suite of new and improved applications (see my preview). And they work in concert with each other in ways that are both exciting and, well, complicated. Not simple.

With that in mind, witness this bit from the aforementioned article:

Mr. Huber countered that I am free to come and go as I wish.

“The nice thing is that we don’t force you to use only our stuff,” he said. “It is not tied tightly together, and the content is all easily exportable. If you feel like we are letting you down, or you don’t like our products or we are failing to innovate, you can pick up and go where you want.”

Microsoft’s online stuff is very much tightly tied together. And while the company gets some props for making Windows Live interoperate with a huge range of third party services, you can’t help but notice that Microsoft can’t help being Microsoft. They didn’t just randomly add Flickr support to Windows Live Photo Gallery one day and Blogger support to Windows Live Writer three days later like Google might have done, noting it only in a blog posting. No, they are releasing a massive and complex platform that will bewilder users. Heck, it bewilders people like me who are pretty well involved in this industry. That’s what Microsoft does. And it’s not necessarily the right approach.

But that’s not all that this triggered.

I want to talk about Windows 7 a bit. I’ve been examining a number of builds of Microsoft’s next operating system for a while now, and I have to say, for all the goodness that’s happening there, there is something wrong, and it’s been stuck in the back of my mind. I haven’t really been able to enunciate what that problem is because I hadn’t really identified it yet. Until this morning.

Reading Mr. Carr’s article, it occurred to me that the problem with Windows 7 is the same thing that’s the problem with Mac OS X. That is, Microsoft is confusing “easy” with “simple.”

For example, Mac users have claimed for years that Mac OS X is “easy to use,” when in fact it is anything but. Mac OS X is simple. As noted above, simple is hard [to engineer]. And we should all give Apple credit for that. But simple is not the same as easy. One basic example: The Mac OS X desktop is a barren place with no obvious starting point. And the people who feel that it is easy are fooled because they are simply used to it. Things that are familiar seem easy. But they’re not necessarily easy to those who are unfamiliar with that thing or, in the case of potential Switchers, are familiar with something else. The Mac OS X desktop is simple. But it is not easy.

By contrast, the Windows desktop is easy in that it provides an obvious starting point (a Start button) and because Microsoft and its PC maker partners go a bit over the top presenting information to the user on first boot. Critics will argue that this also makes Windows convoluted. And they’re right, as it turns out. It’s hard to get the right mix of simple and easy. Apple errs to much on the side of simple, in my opinion. But Microsoft errs somewhere else: They overwhelm the user with functionality in a bid to make sure it works for everyone. All too often, the result is something that works for very few people.

OK, that’s Windows today. But what about Windows 7? As I and others have written, Windows 7 is all about a complete reexamination of the Windows OS. Microsoft has probed into every visible and invisible corner of the system and tweaked virtually everything. The result is, condescendingly, “Vista done right” or, in my mind, simply a very finely tuned tool. As a friend noted via IM the other day, [I’m paraphrasing here], it’s pretty clear that what we’ve seen so far in Windows 7 is it. There’s nothing more coming. And I don’t know whether to be excited by that or freaked.

The problem with Windows 7 is that Microsoft is copying the Mac, again. No, they’ll never really make Windows as simple as Mac OS X, though by God they’re going to try. And the reason they won’t is because you can’t simply erase decades of piling on functionality on top of functionality. Windows will always be a Swiss Army knife. You can’t escape your heritage.

Windows 7 copies Mac OS X in ways that are bad. I will give one specific example here, but save the rest for a more formal article: The new taskbar copies Mac OS X’s terrible Dock by allowing you to mix and match shortcuts (to applications and windows that are not running) and buttons that represent applications and windows that are running. Those running apps and windows can be visible or hidden, and there are subtle changes to the taskbar buttons to note that. You can drag and drop these buttons into any order you want. Looking at my taskbar right now, I see these types of buttons in this order: Shortcut (not running), Shortcut (not running), Shortcut (running), Shortcut (not running), Shortcut (running), Shortcut (running), Shortcut (running), Shortcut (running), Shortcut (running). It’s a mess. It is simple, I guess. But it is not easy to use.

But the Windows 7 taskbar isn’t just a mess because of this one thing. No, the Windows 7 taskbar is a mess because the way it works is not discoverable (i.e. it is simple but not easy). You can do awkward and undiscoverable things like click and drag upward on a button for an active window: This displays the Jump List, a key new feature of Windows 7. What the heck is that? Who would ever do that, other than by mistake? Is that really how we expose new functionality in Windows 7? Yes. Yes, it is. (You can also display a button Jump List by right-clicking, another unnatural action for taskbar buttons, though that one is arguably more easily learned because we do do that elsewhere in Windows.)

Another weirdness. When an application shortcut is “pinned” to the taskbar, it disappears from the Start Menu Most Recently Used (MRU) list. (That’s the list of shortcuts on the left side of the Vista and 7 Start Menu.) So if you already have, say, Firefox running, and you want to open a new Firefox window, doing so from the shell is now very difficult. Too difficult, I’d argue: Simple, but not easy. In Windows Vista, I can simply open the Start Menu and click Firefox, which is the very first icon in the menu. (Or, better still, I can tap WINKEY + DOWN ARROW + ENTER, something I’m very used to doing because I am familiar with Windows.) In Windows 7, Firefox doesn’t appear in the Start Menu because I’ve pinned it to the taskbar. So … how do I open a new Firefox window?

Well, I could use Firefox of course. But how do I do it from the shell? Here’s how: I have to somehow make the existing Firefox button’s Jump List appear and then choose “Mozilla Firefox” from the list. This is bad form for many, many reasons:

1. It’s not discoverable. Where did the Firefox shortcut I’m used to go? There is new functionality—pin to taskbar—but it kills old functionality. In Windows Vista, adding a shortcut to Quick Launch didn’t remove it from the Start Menu.

2. It can and will change. Right now, Mozilla isn’t modifying the Firefox Jump List, so this app gets the default list. But Mozilla will change it in the future. And then the way to open a new window will be different for every application. So much for muscle memory. And I can prove it: In Firefox today, the “Mozilla Firefox” choice is the bottom one on the list. But in IE 8, where Microsoft has in fact modified the jump list, the “Internet Explorer” link, which opens a new window is—guess where … go ahead, guess—that’s right, it’s the top item in the list. Way to go, Microsoft. There’s nothing like inconsistency.

3. When you mouse-over the Firefox button in the taskbar, a preview of existing Firefox windows appears, and you can close individual windows by clicking a little red X next to each. So it’s actually easier to close an existing window now than open a new one because the chance of a user mousing over something is more likely than right-clicking or, heaven forbid, clicking and dragging up.

Now, I could in fact launch Firefox from the Start Menu. But doing so is also convoluted because it’s not in the MRU. So I would have to open All Programs and manually navigate the folder where the icon is located. Simple? I guess. Easy? No.

I will try to flesh this concept out. But here’s my biggest fear: Folks, Windows 7 is in the can. It’s done. There are no major changes coming and Microsoft will ship this much more quickly than many realize. And that’s another way in which Windows 7 is like Mac OS X: This new functionality was implemented without any formal testing at all. Are we really to believe that the company will alter this and other functionality dramatically after the one and only public beta is released in early 2009? I just don’t see it happening.

What Microsoft has done in Windows 7 is mostly good, mostly very, very good. But Microsoft, I feel, is confusing simple with easy in this release. They’re trying to make Windows more like the Mac. And while that may or many not be an improvement over the current convoluted UI model, it’s not the same as making Windows easy.

It’s not the same at all.