Why are Microsoft products so endlessly frustrating to use? Even techno-geeks like me get annoyed by Windows. I’m tired of spending the first 10 minutes of my day rebooting just so I can get to work. Microsoft Outlook 2003, the latest version of the company’s e-mail and calendar software, hangs for me about once a day, requiring me to restart my PC. I also have a problem with Word 2003: Whenever I bullet a line of text, every line in the document gets a bullet. Asking Windows to shut down is more of a request than a command—it might, it might not. And recently, Internet Explorer stopped opening for me.

I know I’m not alone. If you’re like me, you’ve invested in technology to become more efficient and productive but mutter about the many frustrations of the digital lifestyle. Technology is my hobby as well as my job, so I regularly ponder why software giant Microsoft Corp., which has more than $56 billion in cash, hasn’t solved more of these problems.

I began using Microsoft products 23 years ago, at age 11, and I worked for Microsoft from 1991 to 1999 as a technology manager. For many years, I was a Microsoft loyalist. While aware of Microsoft’s shortcomings, I always believed that the Soft did its best to improve products over time, as it did with Windows XP. But recently, I’ve had a crisis of faith. Perhaps I’ve rebooted Windows one too many times.

Over the past year, my frustration with Windows grew, as did my envy of Apple’s cool new products. Finally, last month I went out and bought an Apple Macintosh G5 and began using the new Mac operating system, OS X. It had been years since I’d used a Macintosh. Until recently, I dismissed those who did as impractical, elitist hipsters, and I mocked the Mac “switch” ads on TV.

But in the first five minutes on my new Mac, I was surfing the Internet, sending e-mail, and ripping a CD. OS X has been a breath of badly needed fresh air after Windows.

This made me wonder about Microsoft’s willingness to innovate and compete. Why are Microsoft products still so difficult to use and so unreliable? Why is the company improving them so slowly? Is Microsoft losing its competitive edge? Has the company seen its best days?

Meanwhile, Microsoft doesn’t evoke passion in me anymore. Its products don’t excite me anymore. I remember eagerly looking forward to Outlook 2003, only to be disappointed by how complex, buggy, and unimproved it was. “There’s kind of an angst,” says Andrews, the Seattle Times columnist and author. “Microsoft ought to matter to us. There ought to be more of an intellectual and emotional connection. There just isn’t.”

In an age when retailers hire consultants to analyze what hip kids do, you’d think Microsoft would care more about what the hip kids are doing. They’re running around with iPods, using Linux and OS X. A Groundspring intern e-mailed me recently about his new Apple PowerBook: “I think I may be smitten by a computer.” That’s the kind of passion I’m talking about. In its search for market share, dominance, and profits, Microsoft lost the ultimate battle for our hearts and minds. For now, though, it’s still laughing all the way to the bank.