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The Windows XP/8.1 debacle calls to mind the Wordstar/Wordstar 2000 debacle of the mid-eighties.
Unfamiliar with Wordstar? Exactly my point.
Wordstar ruled the word processor market in the early personal computer market. They weren't just the leader, they were everywhere. The UI was stupid and clunky, but people got used to it. When people in a business setting got a new personal computer, the package they got was: IBM PC (or equivalent); DOS (from IBM, Microsoft or Digital Research), Lotus 1-2-3, a Herculese graphics card, an Epson printer, and Wordstar. Interesting list. How many of those companies are still relevant in the personal computer market?
Wordstar decided to dump their product and move on to new technology: Wordstar 2000. This was not an evolution. New UI. New, incompatible file formats. And get this -- it's really better if you just get a whole new, more powerful computer to run this software.
Microsoft, unlike Wordstar, will survive, but they have thoroughly fucked themselves. Windows 8.1 is the Wordstar 2000 of the twenty-teens.
Adding: "Well, if I got to switch to something unfamiliar and incompatible anyway, what are the other alternatives?" That's the essense of the self-destruction of this sort of move.