Windows 7: Another Reason to Dread the Holidays

It's not even summer yet and if you're like me you're already dreading the holidays. I've never been a big fan of the holiday season, and this year is going to be worse—a lot worse—than most, especially for small business owners like me.

Let me share a few reasons why.

For starters, there's the usual flurry of bonuses to give out—special paychecks to employees; gifts to customers; and cash for armies of service providers, including trash collectors, newspaper deliverers, and mail carriers who materialize out of thin air at year's end. Even the IRS wants an estimated payment around the holidays. Then there's the endless stream of parties and other unproductive events that generate zero revenue yet cost me a ton.

Windows' Bells and Whistles

But the main reason I'm worrying about the holidays now is Microsoft's (MSFT) recent announcement that it plans to release Windows 7, the successor to its three-year-old Vista operating system, at the end of October. This will be in "plenty of time for the holidays," the company says. Humbug.

Microsoft has put all sorts of great features in this newest release. There will be advances in touch and handwriting recognition; support for virtual hard disks; a redesigned calculator; more administrative tools; significantly enhanced security—the list goes on.

But many of these things won't matter much to small business owners. We're still quite happy with eight-year-old Windows XP. We're not gamers. We're not bloggers. We're not tools. We're just not that into all those enhancements. Maybe at home. But at the office, most of us just want something simple that works.

This time, though, we're not going to be given a choice. Microsoft got bruised with Windows Vista and it's trying to avoid a repeat. For now, Microsoft is putting up with both Windows XP and Vista until Windows 7 is released. But as soon as the new operating system hits the street, you can be sure both XP and Vista will be shown the door quickly. I know that Microsoft is "pledging" support for XP through 2014, but I predict its backing of both XP and Vista will be quietly curtailed. I get the feeling that all efforts will be focused on pushing the world onto Windows 7 as a "much better solution." For Microsoft, not for me.

Some Holiday Cheering

Of course, some companies can't wait for Windows 7. The hardware companies are licking their chops. Don't feel sorry for Dell (DELL) and Intel (INTC). I know they've been reporting drops in earnings, but they'll be making it back come year's end. That's because a lot of us small business owners, happy all these years with Windows XP and relieved not to be making hardware purchases, are going to have to buy new hardware. The vendors know this—and they're loving it. They know that the requirements to run Windows 7 are something pretty close to the specs needed to run that supercollider in Switzerland.

So the minute we need Windows support and Microsoft tells us we have to upgrade to Windows 7, the hardware vendors know we'll just throw in the towel and replace the workstation or the laptop or the server. Everyone knows you can't just upgrade to Windows 7. It's always easier to replace the whole damn box. Great news for anyone who makes computers, peripherals, and other hardware; bad news for us business owners trying to conserve a little cash, especially those of us who fail to budget now.

Software companies can't wait for the holidays, either. Santa Ballmer's going to give software vendors the best Christmas present ever. I'm betting the software you're running right now won't be "compatible" with Windows 7, which means you'll be required to upgrade just so that you're "current with the most recent technology." Translation: more money coming out of your pocket and giving you absolutely no benefit. Thankfully, I'm one of those guys that sells software; at least there'll be some Christmas cheer for me out of all of this. As long as I can withstand the withering stares and nasty comments from my clients, who will be justified in blaming me for taking part in the fleecing they're about to endure.

The IT Trap

My IT firm will be loving it, too. These guys will have thousands of reasons to celebrate—and to recommend upgrading. They'll be scaring us with security stories and networking problems and incompatible thingamabobs that will all be magically repaired just by purchasing new computers and Windows 7…all through them! So besides having to replace my software and then get new hardware, all because of the new Windows 7, I'll soon be paying a ton of unnecessary service fees to the unnecessary IT guys to unnecessarily set, reset, screw up, and then set up my whole network again. Yay.

Like 24-hour Christmas radio stations, traffic jams at the malls, tacky lawn displays, and Elf, the holiday season just can't be stopped. And the same goes for Windows 7. No, I can't say no. I can't switch over to Apple (AAPL) or Linux or some other lesser-known operating system. Maybe for my home computer, but not for my business. Most of my software won't run on these systems. There's not enough support out there yet. And it's not like these companies don't have their own bugs, technical problems, and customer service issues like the rest of them. So I'm going to have to upgrade to Windows 7. And pay through the nose all holiday season long.

Before it's here, it's on the Bloomberg Terminal.