Googlebook is a Battle of Simplicity and Sophistication vs. Inertia ⭐

I began dreaming of a simpler, mobile-based personal computing future in the mid-1990s when Microsoft invited me to join the beta for Pegasus, which it went on to market as Windows CE. As difficult as this is to believe, Windows CE--yes, CE originally stood for "consumer electronics," though Microsoft denied this--originally targeted so-called Handheld PCs (HPCs) that would run on early RISC chipsets and offer a grayscale graphical interface modeled on Windows 95. It was Microsoft's response to General Magic's Magic Cap and the Apple Newton.

That focus changed, and quickly, thanks to the success of Palm OS and the pocket-sized personal digital assistant (PDA) form factor it popularized. But before that happened, Microsoft's hardware partners briefly sold mini laptop-like HPCs with real keyboards running a simplified Windows 95-like platform with "Pocket" versions of popular apps like Word and Excel.

A decade earlier, Tandy sold the TRS-80 Model 100, an early DOS-based portable computer beloved by the journalists of that era because it let them write live reports in the field and then file them with the home office using its internal modem. I had missed that wave, but I saw a similar potential in the HPC.

I wasn't the only person obsessed by these new devices. Author and Byte Magazine columnist Jerry Pournelle used an HPC while traveling for longer than was probably prudent, and I was always amazed to see him at trade shows carting around this out-of-date device. But I understand now that he was chasing the same dream I would later chase, that promise of a simpler portable personal computing experience that still delivered the productivity and functionality that writers and others required.

Like Pournelle, I bet, I was eventually betrayed by adopting technology too soon. He did this purposefully, of course, and he was fond of writing that he made mistakes so others wouldn't have to. My mistakes were less well-intentioned, so I likewise became fond of writing that I just make mistakes, and if someone else can learn from those mistakes, great. I documented one such betrayal in The Right Tool for the Job, a 2013 editorial in which I described my experience a decade earlier trying to make a Palm PDA with a portable keyboard work as a laptop of sorts. It did not go well, and the resulting data loss still bothers me today.

But the dream lives on. Most of the experiences I've had using computers, tablets, and mobile devices of all kinds have only served to cement what I learned from that PDA disaster. But every once in a while, something changes. And I wonder whether that future I wanted 30 years ago is finally happening. In recent years, you can see this most clearly in Apple finally expanding the capabilities of the iPad to include full-featured laptop-like productivity experiences.

Apple isn't alone. Microsoft gave up trying to turn Windows CE and its many successors into simpler portable computers, opting instead to chase the...