Boughs, Oranges, and Switching: Considering OS X and Linux

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“One of the things I’d like to do is to show people how to start “positive” epidemics of their own. The virtue of an
epidemic, after all, is that just a little input is enough to get it started, and it can spread very, very quickly.”
Malcolm Gladwell

If I were aiming for brevity, I would say that the current debate raging around the subject Linux, OS X, Windows and the future of operating systems on the desktop began with Mark Pilgrim’s piece succinctly titled, “When the bough breaks“. Among the epiphanies arrived at within that Portrait of the Technologist (and Long Term Mac Fan) as a Middle Aged Man are realizations that a.) Apple’s software is less competitive than it used to be, and b.) migrating away from the less competitive software can be problematic because it’s based on closed, proprietary formats. Those that might criticize Pilgrim for wearing blinders on these topics for the duration of his Mac tenancy have hopefully never behaved irrationally themselves. Glass houses, and all that.

But were I to claim that the conversation began there, I’d be lying (you’d already know that, of course, realizing that brevity is infrequently achieved in this space). Watching the GNOME community over the past couple of years, I’ve seen this same debate play out time after time. Frustrations on both sides – why aren’t you using free software? / I’m developing free software, but I use what I’m most productive and happy on – have occasionally reached boiling points, but more often manifested themselves as good natured trash talking.

Pilgrim’s piece, however, is an important one. It’s important not only because of who Mark Pilgrim is, but because of his personal history. In some respects, this is akin to Gentoo’s Daniel Robbins joining Microsoft (though he subsequently left, I believe). When someone invests a substantial portion of their time and energy into a particular effort – their departure becomes at least mildly shocking. I have personal experience in this matter, despite my complete lack of importance as a hard core technologist; periodically a reporter or editor will transmogrify RedMonk into Redmond and tag that next to my name and title, and within hours I’ll receive a volley of emails asking me how and when I decided to go to work for Microsoft. Put simply, if I were a product manager at Apple and happened across Mark’s piece, I’d be concerned. I don’t know if I’d go so far as to inject the adverb gravely, but I’d consider it. Mark is that important, and that relevant.

The gravity of Mark’s decision was not lost on the wider technology community; cruise around and you’ll likely find a dozen or more related entries. The most interesting of the resulting threads, as far as I’m concerned, are Daring Fireball (John Gruber)’s “And Oranges” and Tim Bray’s “Time to Switch?“. The former was forwarded to me by one of the technologists I respect most with a subject line reading: Must Read. I concur.

Why those two? It’s not that both are written by quality technologists (though they are), or the brilliance of their prose (though it’s quite good); it’s the fact that, like Pilgrim, both are self-confessed Mac geeks. Daring Fireball’s tagline, to wit, is “Mac Nerdery, etc”. It’s been said before that those who with the ability to cut us most deeply, are those that are closest to us, and I’d submit that these three threads are written proof of that Farmer’s Almanac saying. These three erstwhile Mac advocates have convinced me, where evangelists of competitive offerings never could have, not to migrate to OS X.

Now, to be fair, such a switch was not terribly likely. There are a number of reasons that OS X is not the best fit for my needs (despite Cote’s continued lobbying), but the simple fact is that I’m never comfortable on a Mac. I used them in college – my computer at Williams was, in fact, a Mac – but the experience is still jarring to me. This fingernails-on-chalkboard discomfort isn’t attributable to any single factor, but a myriad of design departures. It’s like the tiny little hairs that are left on my neck following a haircut: individually, they’re not a problem, but in aggregate they drive me insane.

But anyhow, I’m getting off track. The point of this entry is not, surprisingly, to comment on the specifics contained within Pilgrims post, or its Bray/Gruber children. For one, I’m not an expert on OS X software as I use it very infrequently. For another, I’ve already submitted feedback to Tim on his concerns with an operating system I know quite a bit more about, Linux (and more specifically, Ubuntu) – and that feedback has been added to the post in question. Thus, I consider my potential contributions to the technical aspects of the discussion not exhausted, precisely, but sufficient for the time being.

What I found most interesting about this whole debate, in fact, was the fact that it transpired at all. I can’t say this with absolute certainty, but it’s my opinion that if Pilgrim decided this two years ago – or even a year ago – it doesn’t go much further. Small hue and cry, perhaps, and a lament for the loss of an important OS X community member, but little more. Why? The same reason that Pilgrim probably couldn’t have decided this two years ago. Where was he going to go?

Which brings us back to Ubuntu. Tim came closest to making this point, when he said:

John Gruber’s essay is very hard to disagree with, but I’d place more weight than either he or Mark did on the increasing excellence of Ubuntu. If you haven’t tried a recent Ubuntu, you really should; the level of polish, and amount of stuff that “Just Works”, is really remarkable. Ubuntu won’t always be the polish-and-quality leader among Linux distros, of course; but for now, it’s set a very high standard.

I’d go even further than Tim, and say that the increasing excellence of Ubuntu is the story here, not the OS X issues.

Try as he might to portray his late breaking OS X frustration as a cumulative event, I view Pilgrim’s long term tenure on OS X as a simple equation: it was the best available option for the last several years. A technologist of Pilgrim’s background and bent was unlikely to be content with Windows, but for the past decade conventional wisdom said that the only viable alternative was OS X. And once upon a time, that statement was true. Today, however, it’s a no longer such a simple equation thanks to the variable known as Ubuntu.

I should note here that there are other distributions, OpenSuSE/SuSE most notably, that are contributing in dramatic fashion to the advance of Linux on the desktop. But Ubuntu really is a phenonmenon unto itself; just ping Jeff Waugh and ask how many Ubuntu CD’s they’ve shipped. The polish and simplicity of the distribution combined with its Debian underpinnings and repository make it the first distribution that I’ve actively contemplated installing for friends and family. It’s that easy. From hardware recognition during installation, to setup of printers, USB keys, digital cameras and iPods, the “just works” grade for the distribution is high. And don’t think I’m the only one that’s noticed; we’re having conversations with multiple software vendors and even hardware vendors (whom I talk to but rarely, but am scheduled to this Friday) about Distrowatch’s #1 Linux variant.

The question that we need to ask ourselves, then, is whether or not converts like Bray and Pilgrim represent a tipping point of sorts. Do they herald the second life of Linux, first as server, now as desktop? The answer to that question, in my opinion, is no, they don’t – no more than Sam Ruby did. Technologists of their caliber are (quite) rare, and basing assumptions on small sample sizes of elite technical minds is statistically problematic. Technical barriers to Linux adoption remain as well – just trust me on this, I’ve been using it for two years.

What Bray and co are, rather, are datapoints – important ones – that indicate that Linux is becoming a viable option for an audience that previously would not have considered it. An audience, albeit, that is more loyal than your typical Windows customer.

Remember, however, that if or when a Tipping Point arrives, it could do so quickly. Very quickly, if you believe Gladwell. Food for thought.


  1. I’ve got some thoughts (that perhaps I should have titled “It’s the software, stupid”) over here:


  2. OSX4Life! In all seriousness, Apple needs to get on being less snooty and jump down in the mud-pit with the glue-code layer morlocks.

    If only there were some firm they could hire to tell them how to build community with that group, and many other types of groups… ;>

  3. Way back in the day (ok, less than 10 years ago) I got stuck managing a development project for a large media/advertising firm that required extensive Mac OS 9 work… Nails on the chalkboard? This was more like the mob cutting off your fingers one at a time, once a week, letting you spend a week staring at it.

    So… this project dragged on forever. Was a nightmare for everyone on the team. Then we got beta releases of OS X (Cheetah I think it was for). What a difference – it was like Apple took my Caldera eDesktop 2.4 Linux (or whatever distro I was on at the time)and just made it absolutely stunning. Sure they had many kinks to fix, but the changes were fantasic compared to 9. With OS X based on Unix, we found an open source app for Linux that nearly fit the bill for what we were trying to write natively to OS 9 and bam – we had an answer. Took the Linux app, fixed some of the bugs compiling it on OS X (a BSD variant I think), and by the time OS X 10.1 came out we launched with a really cool application that also brought along tons of services/migration revenue for our firm upgrading all the desktops/servers to OS X 🙂

    I used OS X from then on until I went into grad school and got back into straight linux again. I miss OS X a bit – even stop by the NYC Apple store just to look at the new stuff – but like Mark points out… why go back to closed apps, closed file formats, and proprietary hardware?? I like the fact that I can put an mbox dir out on a network drive and access it from Windows or Linux.

    Apple had a killer desktop OS – Linux is catching up fast. Anyone using the latest Gnome (and a little XGL) can see the pathway is there. It won’t be long and Apple sure doesn’t have the volumes to support major investments in OS X, iTunes, and iCrappola that it tries to hook people onto.

    Here’s a thought – what if Apple actually supported OS X on all hardware – or at least major vendors like Dell? Hmmm…. I thought OS X would have been a great way to kill Windows XP as an open source tactic. Oh well…

  4. Alex: excellent – good read. could not agree more on the question of portable data. that, in fact, is one of the reasons i believe Google’s important. say what you will about their innovation or product quality – they’re doing more to make the OS less critical than anyone’s done in a while. and that, to me, is good news.

    Cote: if only 😉 good luck getting the time of day from them – i can’t even get responses to inquiries.

    Mike: i’ve been making the Apple “really missed an opportunity to hurt Microsoft by restricting OS X to their hardware” argument for years. frankly, that’s the primary reason i won’t run it. i like their hardware, don’t get me wrong, but it’s a much smaller ecosystem of parts and so on.

    i usually get two responses to that assertion:

    1. support/qa (to which i usually respond – their qa can’t be great given their so-so build quality, but whatever) – and frankly, this is a legitimate issue. one of the most difficult tasks for any operating system – Windows, Linux or OS X – is the hardware support. everyone builds for Windows, OS X has a much smaller focus, and Linux has a wide community. but still, i don’t see this as an insurmountable problem.

    2. they’re a hardware manufacturer, and can’t jeopardize those revenues. to which i usually reply, you’re absolutely right – they are a hardware company. they’re just protecting the wrong piece of hardware.

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