Thinking About Windows in 2020 (Premium)

I’ve been writing about Windows for over 25 years, and while it is still central for me, it has never been less relevant or less well-cared-for by its maker than it is right now. So, yes, I have questions. Lots of questions. And complaints. Lots and lots of complaints.

But first, let’s examine the facts that led us to this time of great uncertainty and see how reality shapes our perception of what can---and most likely will---happen to Windows in 2020.

The first signs of trouble arrived in the early 2000s, when Microsoft was besieged by antitrust action in the United States, Europe, and elsewhere. Many cite the resulting “lost decade” as evidence of Microsoft’s decline, when a demoralized software giant sat by as a new generation of Big Tech---Amazon, Apple, Google, and even Facebook---rose to collectively take its place atop the personal computing industry.

That view is correct, but looking at Windows specifically, it was the broken promises of Longhorn, which was both years late and completely neutered by the time it arrived as Windows Vista, which triggered the great decline. This was when Microsoft’s developer base simply stopped embracing every new SDK and framework that the firm foisted on them. It’s when they stopped listening.

Related to this, the personal computing market went mobile in the 2000s and 2010s, with the back-to-back releases of iPod, iPhone, iPad, and the many copycats of each that appeared in their collective wakes. Today, both Android and iOS command markets that are larger than Windows, in Android's case, many times larger.

Microsoft never responded adequately to these threats. There was little it could do to generate excitement for new application development on the Windows desktop as long ago as the release of Windows Vista. And Steven Sinofsky’s foolhardy push into mobile was just as doomed thanks to his terrible decision-making: Instead of embracing the Windows phone application model for Windows 8, he simply created something that was similar to it, resulting in two incompatible platforms. We’re still reeling from that idiocy. In fact, it was the death blow to Microsoft's mobile ambitions.

Not coincidentally, this month will mark a terrible new milestone: The PC industry has no doubt experienced 8 straight years of decline---the final numbers aren’t in quite yet---and is regardless now under two-thirds the size it was at its peak in 2011. The last time the PC industry sold so few PCs was 2005, when we were still breathlessly waiting for Microsoft to complete Longhorn and change the world.

Microsoft’s inability to extend Windows to new markets over these years is telling. Windows phone eventually failed, thanks to Sinofsky. Microsoft was forced to use Linux to create Azure Sphere because Windows doesn’t scale well enough to work on truly small IoT devices. Windows 10 S/S mode, yet another attempt to wash Windows of its legacy Win32 desktop underpinnings, failed. And ...