It's interesting to think about Bill Gates retiring. When I think back to how much Microsoft has brought us over the years, both happiness and grief, it's a bit of a happy/sad end to an era for me.
Microsoft is what saved us from the TRS-80, and brought us into a world where clone hardware drove prices down to where everyone could afford them. MS-DOS may have been a bad rip off of CP/M and Unix, but to business operations brought us the ability to bring computing power right down to the desk and generally got out of the way. Dos had the neat ability to have TSRs that could deliver waiting applications at a keystroke (remember Sidekick?) Windows 386 and 3.0 brought us preemptive multitasking for DOS apps that weren't written for that in mind, and brought us the first environment the mass market had seen where any manufacturer could write drivers to a known programming interface and bring their hardware to the world. They brought us a world where hardware innovation was bringing crazy new things to us that had only been possible in Sci-Fi movies before. My first voice-recognition system on the computer was in 1990. =)
Windows 95 pushed that even further. No longer were drivers crazy TSRs, but actually loaded into the control panel with standard was of using them for established services such as Networking and Sound. For everything else, the model was extensible so that if you had a neat idea, you could bring it out to the world. I remember installing TwinBridge at work so that people could type in double-wide Chinese characters, despite the OS not being intended for that in the slightest.
Windows 98 brought us games that were better than we were seeing in DOS. DirectX and DirectSound were finally providing a good enough abstraction on top of the hardware that it was easier for authors to code to that than to code right to your Adlib card and whatever display adapter you had (were we using S3s yet, then?)
But that seems to have been the top point of their reign. At this point, as a user I was now so far from the guts of the machine, I no longer could easily tinker. I'd once coded in Z80 asm and 8086 asm to write little hacks, but Windows 98 was getting to the opinionated software stage: There were things you just couldn't do, for no reason other than the designers at Microsoft didn't think it was important.
I realise I'm not the usual mass-market type, but now the system that had been such a source of inspiration was now becoming a barrier to trying new ideas.
I had started playing with Linux in 1995, but 1998 had started to use it as my main machine at home. I had a roommate who had a dumb cheap machine that was slaved off of my main machine so that he could play
Medievia all day and night. Setting up this networking, and the on-demand ISDN dialing was trivial to do under Linux, and nearly impossible under the Windows systems of the time.
The only thing one could say for FVWM95 at the time was that it was better than twm. We suffered through Enlightenment, said hello to wine, and joined an online community of people who'd all come together from various places in order to be free to play with the systems we had.
Microsoft became steadily less relevant to my day to day computing. My girlfriend (now wife) suffered through early incarnations of MS Word for windows 2.0 under Wine because it was still easier than teaching her emacs. And steadily, the system got better until we could honestly look at our family members and tell them that if they wanted to run Windows that was fine, but please don't call me about it.
We need to both say thank-you to Microsoft and learn from it. Microsoft made a business model of bringing us the technology we craved as geeks, and that society wanted to play with and integrated into our lives. Microsoft also taught us what it means to be the dominant player. For most of us, I suspect it was our only view into the world where a single player dominates and strives to cut down its competition. It's easy to romanticise the small business owner, and just as easy to forget that just about every small business owner wants to be a millionaire and a large business owner.
We need to remember that the pretty fancy interfaces can be as much about helping people do things as keeping them from doing things. We need to demand the freedom to tinker with our software and our devices, even if we choose to never do so. And after all that, we need to be able to take our data from a device, and take it to somewhere else. I think ultimately, this is what Microsoft has taught us. As we look for new companies to deliver us greater and shinier technology, this is a lesson we need to keep close at hand.