In 1998, while on vacation, I recall having an idea about a new kind of computer. A computer where you could  use it as a laptop, or flip the display around and use it with your fingers. I let the idea pass, since I figured it was novel, but nobody would pay a premium price for such a device.

Several years later, I recall when Windows Tablet PC was in it’s infancy, seeing a convertible Tablet PC, and thinking, “maybe it wasn’t so stupid”.

If you look deeply into the soul of Microsoft, there are two things that have driven them like an obsession of some sort for decades. The first was IPTV – broadcast television over IP networks. Through tons of research, investment, and inventions, the end result is primarily Mediaroom – the technology behind AT&T U-verse and similar offerings. The second such obsession was pen-based computing. For more than 20 years, Microsoft has pursued a vision of pen-based computing – perhaps to a fault.

Windows for Pen Computing (German Google translation) released in 1991, 11 years before Microsoft’s next big surge in pen computing, Windows XP Tablet PC Edition (2002). Microsoft significantly enhanced how the OS itself interoperated with the pen, but in both operating systems, the pen became an adjunct to the computer. It still felt tacked on.

I worked on Windows during and after Windows XP – and was on the setup team when the Tablet PC (and Media Center) code was being chemically bonded into the OS using a second CD approach. I recall from the very get go thinking that if Tablet PC was real, maybe I should switch my main computer to be one. When I had the chance, I ordered a new Motion Computing M1200. This was, as very few were, a slate-style Tablet PC. In general, Tablet PCs came in two forms. Convertible devices which compromised weight and dedication to being a tablet with being a standard laptop or a tablet, or slate-style devices, which limited their utility by not having a dedicated keyboard – much like the iPad and Android tablets now do.

I originally ordered my Motion without a keyboard – just the device with it’s built in stylus. Within weeks I realized I needed a keyboard, and Motion Computing had a relatively complex fabric case that flipped and unfurled to allow their keyboard (USB) to sit below the device while it was propped at an angle. It was, in some senses, an ungainly early version of the Apple Smart Cover. Only when I used this device, people laughed, since it was so ungainly and since I was needing to attach a keyboard to a device designed primarily to not need one.

I have not tried more recent vintages of Tablet PC since 2005. I believe it has improved dramatically in how it recognizes handwriting – or at a minimum, how it captures it and lets you search it later, even if not recognized and converted to text. But I’m a firm believer that for most of us – unless you’re a horrible typist – you’re better off with a keyboard and a tablet than you are with a pen and a tablet. Tablet PC was, in the end, good for two roles. It was useful for point of service (where Motion Computing focuses today) where simple handwriting input either made sense or was a requirement, and it was useful for some people who needed to take prolific notes but do so faster with a pen than they could with a keyboard.

I’ve known for most of my life that I have awful handwriting. I’ll admit it. It’s horrible. But I think that was only part of the problem.

The two fundamental problems with Tablet PC were – and this was painfully clear when I ordered my M1200 and when I used it later – the devices were obscenely overpriced compared to laptops at the time, and they still required a keyboard. While they tried to be tablet PCs and laptops, they weren’t terribly good at either. They came with smaller screens than most laptops at the time (the Motion, with a 12.1″ screen was one of the larger Tablet PCs of the era), and when it came time to use them as a tablet, the only thing you really got for it was handwriting input where you could use it (OneNote and a handful of other apps tuned for Tablet PC, plus a few games), and a glorified hand-held mouse where you couldn’t.

Unlike iOS, and now Metro-style apps in Windows 8, where touch is intrinsic – and in fact the OS is even seemingly detuned for the mouse, when you got a Tablet PC, you were in this weird middle ground where it was still Windows, and very few apps took advantage of the fact that you had a pen, yet you didn’t always have a keyboard, and usually had a small screen – compromising what Windows could actually do for you.

I wound up hardly ever using the pen on my Motion. When I moved groups not long before I left Microsoft, my Motion stayed behind for clerical reasons – and I got a new ThinkPad that I found much more usable. With a few exceptions here and there until I got my iPad, I’ve hardly ever missed having a Tablet PC. The apps still haven’t arrived for Windows pen computing.

I think Steve Jobs was wrong – there isn’t anything intrinsically wrong with a stylus. I have one for my iPad. For some detail work as you’re drawing, it’s invaluable. I wish that the iPad had a decent stylus option with wrist detection – something Windows can handle today. But for me, handwriting as a primary input is a novelty – a parlor trick. There is a certain romance to handwritten text, and perhaps some writers still work best when putting pen to paper (or stylus to tablet). But for me, with the technology available, it’s illogical to write in a format that doesn’t seamlessly convert to text reliably and rapidly, when I can type with a faster velocity, and iterate on it from there. I don’t think the stylus is dead – but I also don’t think that most consumers will ever switch from typing to handwriting. We’ve left the era when handwriting will be a primary input. The keyboard – it’s oddball QWERTY layout and everything, lends itself to easy, high-velocity text input that is reusable, recognizable, and universal. Even as we move to a world that grows to accept touch and broad gesture manipulation, I don’t see the keyboard (physical or virtual) going away to have pen come back to prominence. Handwriting as an input for digital media is to me similar to the ink and quill of centuries ago, or even the annoyance of standardized testing that required a #2 pencil on a standardized form. More work than it is worth. Maybe the stylus will rise again. For now, I’m just not seeing it happen.