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Windows 10sion: what's old is new again, and that's a problem

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There was never really any doubt that the next version of Windows was going to look at least a little like Windows 7. Even Windows 8.1 was a step back in that direction for Microsoft, bringing back the Start button that so many millions of customers missed. But for all the time Terry Myerson and Joe Belfiore spent on stage today explaining the enormity of change in Windows 10 — they skipped a version number to prove the point — there's no obscuring the blindingly obvious truth.

Windows 10 is Windows 7.

Windows 10 is Windows 7 plus a handful of the things about Windows 8 that worked best: Snap mode, beautiful Modern-style apps, always-updating live tiles, and now (finally) a universal app store that works across all screen sizes from phones to TVs. But it's still Windows 7. Windows 10 is based primarily on the desktop, not the radical new Start Screen of Windows 8; you'll find most things by going to the new-old Start Menu. "Everything runs in a window" is billed as an exciting new feature. There are bits and pieces of Windows 8 here, but Windows 10 will be more jarring for Windows 8 users than for users who haven't updated their computer software since 2006.

"You already know how to use it" doesn't mean what Microsoft thinks it means

That is, of course, the whole point. "Familiar" was a favorite word of Myerson's and Belfiore's. They described over and over how simple it is to upgrade, how similar Windows 10 will feel to what you've already been using. "We want all these Windows 7 users to have the sentiment that yesterday they were driving a first-generation Prius," Belfiore said. "And now with Windows 10 it's like a Tesla." It's not supposed to feel different, it's not supposed to be scary.

It's supposed to be Windows 7.

It's telling that throughout its entire event, Microsoft seemed to be speaking not to Windows 8 users, but to the customers who took one look at live tiles and decided to stick with Windows 7 or Windows XP.

Those fearful upgraders are largely business customers, which clearly hasn't escaped Microsoft's notice — the enterprise is Windows' great stronghold and its most important customer base. (The command prompt even got prominent demo time during Microsoft's presentation; you can paste in it now!) Even the invite for today’s event specified showing "what’s next for Windows and the enterprise." With Windows 10 for the desktop, Microsoft is letting businesses customize the store, silo personal and corporate data away from one another, and more, but mostly it's letting them get back to work on a computer they actually know how to use.

This is a smart, pragmatic, and clearly responsive move from Microsoft. It turned boldly in a new direction with Windows 8, and received massively negative feedback. As Belfiore and Myerson said at today's event, the problem wasn't that the features didn't work or that everything was too damn colorful. It was that there was too much training involved — Windows 8 is just way too hard to learn, and most people just didn't want to go through the trouble. So Microsoft kept as much Windows 8 as it could, while reverting the core pieces of the operating system back to something people know and understand.

In doing so, however, Microsoft finds itself playing a dangerous game. For all that it wasn't, Windows 8 was at the very least an attempt to discover new and better ways of interacting with our devices. We wouldn't need to go looking for information, Microsoft imagined: a live tile would just flip over and what’s new would be there on your screen. The "desktop," that strange repository for your background and files without a better home, was dead. Apps would work everywhere and always be up to date, no matter what device you used or the size of its screen.

With most or all of those ideas undone or at least de-emphasized — when you use the touch screen you get Continuum, which adds some of the Metro shell on top of the desktop and turns on a back button – Windows 10 feels like a platform that hasn't seen serious or meaningful change in eight years. Apps have gotten much more powerful and there's a handy way to search everything, but when you pick up a Windows PC it may not be immediately clear which decade it comes from. It's the best Windows 7 ever, but it's still Windows 7.

If that's all Microsoft has up its sleeve, that's a problem. If it allows its most resistive customers to slow its pace of innovation, Microsoft will essentially back itself into a corner from which it will have no choice but to watch its competitors race past it toward the next device type or the next interaction method.

There's a long time left before Windows 10 comes to market in 2015, and there's a lot more of the platform left to see. We've only seen the desktop side of the equation, for one thing — how Windows 10 will look on phones and other touch-first devices is a big unknown. And for many users, a vastly improved Windows 7 is going to be a great improvement over everything that came before. But what we saw today in San Francisco worries me, and it should worry anyone who wants Microsoft to succeed long term. This looks like a Microsoft that is unwilling to try things, one either without good ideas or without the confidence to commit to the good ideas it's already had. Windows 8 was an attempt to reinvent the way we use our most important and most personal devices, but now Microsoft doesn't even seem to be trying.

Familiar is easy, it's safe, it's probably profitable. But in an industry that moves as fast as technology, familiar is dangerous.

(Updated 6:08 PM to better clarify Continuum, which I had over-simplified before.)