We Need a Better Plan for Windows (Premium)

While this week's impromptu drama over the fate of Microsoft Paint was a lot of fun, it's only a small example of what's wrong with Windows. And I think we need a better plan.

The set up is simple enough: Here's Windows with its massive, decades-old code base, and a billion-strong user base. And it has no future. No future at all.

Just as surely as Windows phone was doomed from the get-go, Windows---Windows on the desktop---is likewise doomed. I've kind of tiptoed around this one in the past, have tried to soften the blow by noting that this doesn't mean that Windows disappears overnight. That we will be using it for years to come, and we will be utilizing our familiar skills to get work done well into our retirements.

This is all true. But it also obscures a central truth: Microsoft will never put the required resources into Windows to truly modernize it, because doing so is too arduous and expensive, and because the software giant is racing forward with the products and services that may generate most of its profits and revenues in the future. You know, after its digital transformation is complete.

Windows, put simply, is the past. And it is in maintenance mode.

Microsoft won't---can't---admit this. And let's consider Windows phone again to see why. If Microsoft cannot explicitly stand up on a stage, or clearly write in a press release, that Windows phone is no longer a thing, that it is no longer actively developing a mobile operating system that runs on phones, then how on earth can it do the same for a platform with over one billion users?

It can't. And it won't.

But this inability to communicate this truth is leading to all kinds of horrible side-effects for those billion people. And that is, of course, what I'm concerned about most: Not Microsoft. But those people who use Microsoft's products every day. Folks, I've been doing this for about 25 years now, and it still continues to amaze me that readers and listeners misunderstand my relationship with this company. I care about you. Us. Not about some corporation. Which, quite frankly, has very different goals, tied to financial growth and new markets, that stand in opposition to what Windows really needs today.

Here's what Windows doesn't need.

To be updated with major new product versions twice every year, double the rate at which simpler, more mobile platforms like Android and iOS are updated.

To be spray-painted with an endless array of pointless new in-box features that few will ever use, like an e-book store that is tied to a web browser no one even wants, Cortana yelling at us during Setup, or MyPeople, which I assume needs no explanation.

To have the foundational and fundamental parts of Windows---like File Explorer and the file system, mouse input, and typing---ignored and not modernized while those goofy new features are added.

To have a special product version, called Windows 10 S, developed in secret, and then updated in secret, with no...

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