Chris blogs regularly at chris.pirillo.com, entertains geeks in bLaugh.com, drives an experts’ blog network at Lockergnome.com, and hosts a conference through Gnomedex.com. Essentially, he lives his life on the Web, with many of his favorite desktop applications having already been replaced by various Internet services. This article was written in Microsoft Word 2007 on Windows XP SP2, but it could easily have been composed in a plain text editor on any operating system dating back to the digital Stone Age.

A few months before this article was published, I posted to my personal blog:

“When I have the time, I’m ‘upgrading’ from Windows Vista to Windows XP. My keyboard is completely ambiguous. I stand by my original assertion that the shipping version of this OS is late beta, at best. I realize that other enthusiasts are leaving Windows altogether (and leaping instead to Apple’s OS X), but there’s not yet enough momentum behind my willingness to do that. I’ll leave the installs of Vista 32 and 64 on this PC, but I’ll spend most (if not all) of my time back in tried-and-true Windows XP.”

Since I originally published my primary reasons for switching from Windows Vista back to WinXP (largely related to hardware and driver support issues), three Microsoft community influencers have contacted me privately to say that: (a) they’ve just switched from Windows to OS X, running Windows as a VM (virtual machine) in Parallels; or (b) they’re getting ready to make the switch.

You would be stunned—shocked—to discover who these people are.

Then again, for political reasons, they may choose to keep their switching a complete secret indefinitely (or, at least, not publicize it very much). Why? It’s probably the same lynch mob that keeps telling me it’s not Vista’s fault for my problems; it’s either my problem or a problem with third-party developers. Either way, I don’t think I can stay with Vista too much longer.

And I really don’t think the grass is greener on the other side, either. As tempting as Leopard appears to be, Apple’s universe serves up its own set of challenges. I don’t want to invest thousands of dollars in new hardware and software only to discover that what I had in WinXP was more than good enough. Then again, the next version of Windows is at least two full years away and will likely be a complete departure from what we know Windows to be today; I’m going to have frustrations no matter what.

I love—and I mean LOVE—Microsoft and many of the people who work there. Hell, if I had a dream job, “Microsoft” would probably be somewhere in the description. Then again, so would the words “brand agnostic.” But Microsoft isn’t just about Windows, eh? I freakin’ love the Xbox 360s strewn about my house and can’t wait to see what’s coming in future firmware revisions. I can’t wait to see the next version of Entourage on OS X. I’m looking forward to the day my Microsoft Entertainment Desktop 8000 finally ships!

OS X (in complete conjunction with Boot Camp and Parallels) could deal a striking blow to the world of Windows, but the following three impossible things must happen for the market to change significantly:

• Apple must be more competitive with hardware pricing.
• Apple must acquire Parallels and bake it into the operating system.
• Apple must start selling machines with the option of having Windows preinstalled.

If Apple really wanted to change the world:

• Apple should open-source more of its software, like iPhoto and iTunes (or more importantly, the iPod).
• Apple should pause Safari development and pick up the Firefox ball instead.
• Apple should start blogging and start letting its employees blog publicly.

I dunno. It seems that Windows doesn’t have much to worry about until those “musts” and “shoulds” become “dids.” That’ll never happen, so we’re back at ground zero. (Sorry, I still do not and cannot see Linux as a desktop OS in the foreseeable future.)

And if I, as a technologist, am undecided, what do you think is running through the minds of Joe and Judy User? I can tell you one thing: The less technically sophisticated you are and the more you live your life online, the easier it is to switch between operating systems.

Microsoft would be wise to start spending more time developing for OS X. There may come a time when the world sees Windows as just that—windows on a desktop of a non-Microsoft OS.

You can dialogue with Chris at chris@cpumag.com.