A year and a half into Microsoft reimagining itself as a devices and services company, we're still seeing a lot of pushback from customers. But while there are many technical issues to overcome across the board, what I'm hearing from both individuals and businesses suggests that the biggest blocker to this change isn't technological but is instead psychological.

Newly minted Microsoft CEO Satya Nadella subtly and correctly addressed this problem in his formal introduction to employees when he repeatedly used a word—software—that had grown out of favor during Microsoft's previous push to drive home the devices and services vision. He's a smart guy, and this usage was calculated: Many critics of the devices and services strategy believe that Microsoft—long known as the world's largest maker of software—was sacrificing both its past and its reputation to bet big on the unknown and the unproven.

"This is a software-powered world," Mr. Nadella wrote in his open letter to employees, channeling the Bill Gates' "magic of software" vibe. "Microsoft uniquely empowers people to 'do more' . . . This is the core of who we are, and driving this core value in all that we do, be it the cloud or device experiences, is why we are here."

If you find this language soothing—and I suspect many of Microsoft's customers do—then consider for a moment why so many of you find the notion of devices and services to be so alarming.

The short answer is that these things represent change, and not just minor change, but sea change. A change that changes everything, if you will, in profound ways. Many of the technology decisions we make each day are based in large part on experience, or what we might call tradition, and by breaking away from its own tradition, and asking customers to follow it down this dark and uncertain path, the firm scared customers instead of exciting them.

Microsoft isn't changing its strategy. The future is still devices and services. But with a subtle shift in language—devices powered by Microsoft software, and services that are modern and connected versions of Microsoft software we all understand and use—this change in some ways seems more manageable. I expect to hear the word "software" a lot from Microsoft in the coming year. At BUILD in April. At TechEd in May. And beyond.

I'm not a psychologist. But it seems to me that in my own technology transitions, managing change—especially big change—often comes down to the simple concept of letting go. Some people require things to be very regimental, to the point where formal processes become those traditions and we lose sight of why we did things that way in the first place. Others are obviously a bit looser in every sense of the word.

Here's an example that's not business related, but one that maybe many of you can relate to.

In the late 1990s, a friend began touting a digital music format called MP3. Looking into it, I saw something that, at the time, was a non-starter: A typical song file required about 5MB, meaning I'd be hard pressed to store more than a few albums worth of music on the hard drives I had at the time. Over time, of course, hard drive sizes increased nicely and MP3s took off. So I dove in.

As a music fan, I started converting my own CDs laboriously to digital formats. As a compulsive, technical guy, I did this repeatedly over time, as new formats and possibilities emerged. I can recall a few of these collection conversions: the initial 160Kbps MP3 versions, the 128Kbps WMA versions, and then most recently the 256Kbps AAC versions. But what I really remember was the sheer amount of time I spent carting that collection around, copying it from PC to PC, backing it up, reconstructing my carefully made playlists, reconstituting and correcting lost album art, and other assorted stupidity. It's embarrassing to admit, but I bet I spent more time managing my music collection over a decade than I did listening to it. As is so often the case for people like us, technology became the end, not the means.

Today, I've learned to let go, at least as much as I can. (Being compulsive is a sickness that's almost certainly as hard-wired as any addiction and is something you have to fight constantly.) So I use a cloud-based music service, in my case Xbox Music, and I access that music from various devices. Xbox Music doesn't have every one of my songs. And it certainly doesn't have all of my carefully made playlists, though I could spend this entire year fighting it to get these things as close as possible to complete. But I've decided to let go. It's good enough.

I get email regularly from people who simply can't use this service, or other services that have nothing to do with music, because it lacks that one crucial thing that makes them happy. What they can't do without is really just a tradition, even though in many cases there are better or at least different ways to get to the same place.

PC hardware is the same, and the reaction we see to both Windows 8 and the crazy, transforming devices on which it runs says a lot about people's inability to evolve. (This doesn't excuse the very real issues with Windows 8, of course.) For example, many people have said to me that what they want is a better version of Windows 7. To which I reply, then get Windows 8. If you pretend that the Metro environment doesn't exist and just focus on the changes to the desktop environment, Windows 8 is a bigger leap over Windows 7 than that release was over its predecessor.

Many can't see this. What they do see—in fact, all they see—is the unwanted comingling of a new mobile environment with the desktop. And their blood boils. They refuse to use Windows 8 because they're so mad at Microsoft. But what they're really doing is hurting themselves. That Metro stuff is actually pretty avoidable, especially with the free Windows 8.1 update. They're denying themselves, even hurting themselves, to make a point that will affect no one but themselves. They need to let go.

Like others at Windows IT Pro, and like many readers, I try to fight the good fight, call out Microsoft when it screws up, and applaud when the firm gets something profoundly right. But whatever opinions we might have should never stand in the way of being pragmatic, using the right tool for the job, and moving forward when it makes sense to do so. The shift to devices and services is happening all around us—and Microsoft is riding that wave, hoping to emerge as a leader. We're all getting swept up in it too, whether we want to or not. And rather than fight the change, perhaps the focus should be on managing the change and ensuring that we emerge on the other side as more agile and open-minded.

In other words, maybe it's time to let go.