While reading Dave Winer's Why Windows Lost to Mac post, I noticed many parallels with my own experience with Linux and the Mac. I will borrow the timeline from Dave's post.
I invested years of my life on the Linux desktop first as a personal passion (Gnome) and when while awoken for two Linux companies (my own, Ximian and then Novell). During this period, I believed strongly in dogfooding our own products. I believed that both me and my team had to use the software we wrote and catch bugs and errors before it reached our users. We were pretty strict about it: both from an ideological point of view, back in the days of all-software-will-be-free, and then practically - during my tamer business days. I routinely chastised fellow team members that had opted for the easy path and avoided our Linux products.
While I had Macs at Novell (to support Mono on MacOS), it would take a couple of years before I used a Mac regularly. In some vacation to Brazil around 2008 or so, I decided to only take the Mac for the trip and learn to live with the OS as a user, not just as a developer.
Computing-wise that three week vacation turned out to be very relaxing. Machine would suspend and resume without problem, WiFi just worked, audio did not stop working, I spent three weeks without having to recompile the kernel to adjust this or that, nor fighting the video drivers, or deal with the bizarre and random speed degradation that my ThinkPad suffered.
While I missed the comprehensive Linux toolchain and userland, I did not miss having to chase the proper package for my current version of Linux, or beg someone to package something. Binaries just worked.
From this point on, using the Mac was a part-time gig for me. During the Novell layoffs, I returned my laptop to Novell and I was left with only one Linux desktop computer at home. I purchased a Mac laptop and while I fully intended to keep using Linux, the dogfooding driver was no longer there.
Dave Winer writes, regarding Windows:
Back to 2005, the first thing I noticed about the white Mac laptop, that aside from being a really nice computer, there was no malware. In 2005, Windows was a horror. Once a virus got on your machine, that was pretty much it. And Microsoft wasn't doing much to stop the infestation. For a long time they didn't even see it as their problem. In retrospect, it was the computer equivalent of Three Mile Island or Chernobyl.
To me, the fragmentation of Linux as a platform, the multiple incompatible distros, and the incompatibilities across versions of the same distro were my Three Mile Island/Chernobyl.
Without noticing, I stopped turning on the screen for my Linux machine during 2012. By the time I moved to a new apartment in October of 2012, I did not even bother plugging the machine back and to this date, I have yet to turn it on.
Even during all of my dogfooding and Linux advocacy days, whenever I had to recommend a computer to a single new user, I recommended a Mac. And whenever I gave away computer gifts to friends and family, it was always a Mac. Linux just never managed to cross the desktop chasm.