Remember that kid you knew in high school, the one who started playing baseball or soccer or football when he was in elementary school and kept doing it until he was a starter on the varsity team? Or maybe he was a photographer, or a painter, or a writer, and just made it seem effortless. He was friendly, and he made a point of suggesting that everyone start doing it. Maybe you even took him up on the offer. Maybe you’re still doing whatever it is that kid did.

Do you remember being surprised, a little startled, when you found out that he’d given it up—packed up his bags, and moved on?

Mark Pilgrim’s highly publicized switch this month from the Macintosh platform to Ubuntu Linux on a Lenovo ThinkCentre made the kind of waves that only that kid from high school could.

Pilgrim was a longtime Mac power-user and hacker, and an early blogger, whose collection of software and writing was highly influential to a great many of us. Like me. I wouldn’t say that I bought my first Mac because of Pilgrim’s writing, but I think it’s fair to say also that I might not have had the kernel of an idea that buying one was the right decision without his help.

So on June 2, when he announced that he’d walked into an Apple store and walked out without buying a new computer, and instead had bought a PC, many of us were genuinely stunned. It was not a hardware decision for him, but a software decision: as an open-source enthusiast, Pilgrim wanted open data formats and open code, and Apple has a history of providing neither. He wrote:

And what about those wonderful Apple programs that I haven’t replaced with open-source alternatives? I loved iPhoto until my iPhoto database got corrupted one day, and I lost all my ratings, keywords, and albums because that information is stored in an undocumented binary black hole. Yeah yeah, I know about AlbumData.xml. That has its own problems, and in my case it was already corrupted by the time iPhoto noticed. I’ll give them some credit for trying.

Similarly, I loved iTunes until my iTunes database got corrupted, too. Once again, I lost all my ratings and about two dozen well-thought-out interlocking “smart” playlists. And once again, all of the irreplaceable metadata was stored in an undocumented binary black hole. Yeah yeah, the XML backup again. iTunes even helpfully offered to restore from it… except that it didn’t restore any of my aforementioned metadata, so it’s not really a backup, is it? “A” for effort, “D-” for implementation.

[…]

I’m creating things now that I want to be able to read, hear, watch, search, and filter 50 years from now. Despite all their emphasis on content creators, Apple has made it clear that they do not share this goal. Openness is not a cargo cult. Some get it, some don’t. Apple doesn’t.

About as soon as he posted about this, the feedback started flooding in, many from Mac users who sounded angry and betrayed by the loss of a highly publicized figure. It’s a little like finding out that your representative or senator, or the head of your political party, just switched to the other party. An aside: those of you who remember when Vermont Senator Jim Jeffords became an independent in early 2001 may recognize some of the screaming, angry vitriol in the comments on Pilgrim’s initial entry.

That was where John Gruber got involved. He is, as always, an excellent and level-headed analyst, and his take on Pilgrim’s argument can be reduced to a quick punch: he thinks it’s worth exchanging a little openness for a better and more intuitive user interface, but not everyone does. Gruber makes the neat analogy that reminding the reverse-switcher that his new UI is not as good is “like telling someone who is switching from a Chevy Tahoe to a Toyota Prius that he’s not going to have as much cargo room. He knows it.”

Gruber seems to believe, as I always have, in the relativism of operating systems. Now, that’s my facetious shorthand for saying that for each user there is a best operating system, and that it is not necessarily OS X. And if, like Mark Pilgrim, you are extremely worried about open formats and open source code, OS X cannot be the best operating system for you.

Mark Pilgrim responded with an exhaustive list of all the times that, in fact, his data or code were broken by Apple, starting in 1983. He also makes the fair point that extinct data formats are much more easily converted when they’re documented.

But this wasn’t just a two-person conversation, plus a bunch of jumping-up-and-down ranters in the comments box. It provoked the question, “Is it time for me to switch?” in Tim Bray and Ted Leung, who are both prominent Mac users and serious open-source evangelists as well. Bray breaks down his list into things that would already make it easy for him to switch, things that are sticky, and things that are keeping him on a Mac, notably projection and fast resume-from-sleep. I would note, though, that some of the best open-source software either runs on Macs or is OS X–native, like Adium and Firefox. He also thinks Apple should open-source some of its applications. (Gruber writes, later: Sure, but they won’t.)

Leung suggests that it’s just a matter of time before he starts using Linux as his primary operating system, that there’s just a certain degree of spit and polish Linux needs before he’ll port all of his data over. He, too, lists features that he expects from Linux: better font support, scriptable applications, color management, something like iSync, and more great applications.

I’m not sure how possible these are. Eric S. Raymond’s bazaar model may get the job done, but UI spit and polish is hard labor in the salt mines, and very few people will do that for free. On that note, Rui Carmo says that developing software is like cooking, where even if you have the instructions or source code, getting it just right requires a great deal of know-how, something the casual cook might not have. I think it’s a reasonable point.

At any rate, good luck, gentlemen. And godspeed, Mark Pilgrim.