
I’ve closely followed the one-time key competitor to Windows for decades, and I’ve always owned at least one Mac. But many misunderstand my relationship with Apple’s desktop platform. I’m not sure that even I understand it.
But it goes something like this. Endlessly fascinating. Great hardware. Software with some big hits and some equally big misses.
Studying how Apple has evolved Mac—both the hardware and the macOS platform—over the years is instructive for any Windows fan. Apple and Microsoft are roughly the same age, and both companies competed head-to-head for many years. There were successes and defeats on both sides. And the fact that Apple is now a much bigger and more successful company than Microsoft is only interesting in that the Mac had nothing—literally nothing—to do with that success.
The parallels are endless. Here in the waning days of 2017, Microsoft is keeping the dream of Windows and the PC—the platform on which it once gained control of the personal technology industry—-alive via new initiatives like the Windows Insider program and cross-platform integration with Android and Apple’s iOS. Apple, meanwhile, is keeping the Mac drive alive, too, by bringing some great ideas from iOS to the desktop and by aggressively courting new technologies.
There are difference, of course. Where Microsoft has embraced active pens and then multi-touch in Windows, Apple has declined, on both counts, to do so on the Mac. Apple argues that these technologies have more place on mobile. But I feel like this has more to do with keeping their prize pig fat and happy. That is, the Mac has been denied pen and touch only because iOS is so much more successful. It’s almost incalculably more successful, and Apple has been talking up the “post-PC” world for so long that some have simply forgotten that a Mac is a PC.
Anyway, strategy is what it is, and both companies are driven by forces both internal and external. That both take different approaches to the desktop is what makes life interesting, at least to me. There is a lot to discuss here.
But let me start with this. I’ve been using a Mac regularly since roughly 2000, when I purchased my first Mac, an iBook. At that time, Mac OS X, as it was then known, was incomplete, but you could dual boot between whatever classic Mac OS version (8, maybe. 9?) and Mac OS X.
But I was only interested in Mac OS X.
An eager student of personal computing history, I had come of age reading every book ever published about Microsoft, Bill Gates, and Paul Allen, and about Apple and Steve Jobs. I poured through early accounts of Steve Jobs’s NeXT, and of its pushes for advanced graphical and audio interfaces, object-oriented programming, and elegant hardware. Watched as it crashed and burned, and failed. Watch as the idiot Gil Amelio resurrected Jobs and sealed his own fate. Watched as Jobs and Next staged a coup of Apple and turned it into a different company.
Fascinating, all of it. But it was the products I really cared about. Jobs and Apple planned to evolve OpenStep, the cross-platform version of NextStep, into a future version of Mac OS. This would bring a product I could only dream of using in the 1990s to the mainstream—or at least the well-heeled mainstream—and Apple would once again battle directly with Microsoft and Windows.
I still get excited just thinking about these days. I love a good fight.

So I’ve used various Macs, and every version of macOS–as Mac OS X is now known—since then. Every single version. I’ve spent all of the past several years on the Apple Developer Program—was on both the iOS and Mac programs back when they were separate programs—so that I could keep on future versions of these platforms. I still pay Apple $100 a year for this privilege.
Of course, most of you understand that this is what I do, at least generally. I wrote about the need to embrace change recently, and I used a few examples of how I apply this mantra, this approach to life, in my own way. The Mac is another great example. Because I don’t feel that I can accurately explain to anyone why and when, say, Windows is “better” than the Mac if I don’t really know it to be true.

Looked at a slightly different way, change is about experimentation. And not every experiment will result in change. But when it happens, it’s a big deal. For example, this year, I switched from Google Chrome to Mozilla Firefox, and I do so everywhere: On my PCs, my phones, and even my tablets (which are Apple products). You can’t know this is possible if you don’t try.
(I was interested to read a New York Times editorial this morning that touches on this very topic. “Experimentation is an act of humility, an acknowledgment that there is simply no way of knowing without trying something different,” the author notes. There’s a great example about the London Tube in there. Totally worth reading.)

So what about the Mac?
Over the past 20-plus years, as the Mac has evolved and improved, I’ve received many messages from readers that basically say, “Come on, admit it. You’d much rather use a Mac.” Something along those lines. The idea, I think, is that I’ve been living some kind of a lie, that I really do prefer the Mac, or Apple’s products generally, and that I simply latched onto Microsoft and Windows for reasons beyond preference or enthusiasm.

But in sharp contrast to how much things have changed since the mid-1990s, one thing has not changed: That assertion, that I believe the Mac to be “better” than Windows, or is something I’d personally prefer using, is untrue. It’s always been untrue.
I will keep trying, of course. That is what I do. But I really do prefer Windows and the PC, and I can say that after owning many, many Macs and an almost uncountable number of Apple devices. I can state it firmly, based on real experience. I am literally positive that I have own more Apple products, have spent more of my own money on Apple products, than every single person who has levied that accusation at me. Which is both ironic and funny, when you think about it.
Here’s where I stand on the Mac today, and it’s important to differentiate today from, say, 10 or 15 years ago, when Apple was pretty much stuck advancing the Mac as its only meaningful strategy. Back then, Apple led the way in some areas, and it added technologies like hardware-accelerated graphics and scalable displays well before Microsoft did with Windows. (Microsoft tried with pens and media centers, but none of that was ever really successful.)
The Mac is still very interesting, for the strategic differences noted above. It is less intuitive to use than Windows, on one hand, more Spartan and less friendly. But there’s a spazziness and inconsistency to Windows, where the Mac is at least consistent.
I find the Mac to be less productive, a claim that many have decried. Part of it is absolutely familiarity: I do use Windows much, much more than I use any Mac. But there are little niceties in Windows—like the ability to type ALT + F or some other keyboard shortcut to open a menu, or the ability to TAB-select every control in dialog or window—that simply do not exist on the Mac. So it’s less efficient, unless you believe that taking your hands off the keyboard to grab the mouse, or swipe a touchpad, is somehow more efficient. Hint: It’s not.
Here’s another one. Apple fans saluted the arrival of Touch ID, which lets you use your fingerprint to sign-in, to the Mac in late 2016. That was about 10 years after Windows PCs had such a feature, and with Windows 8 or newer, we can sign-in to the system with smart cards, PINs, and even on-screen gestures. With the Mac, you get a password. Hope it’s not too long, because you’ll have to type it a lot. Maybe you should buy one of the few Macs with Touch ID: The cheapest one costs $1599.
But … OK. Familiarity is what it is. If you use a Mac, you simply adapt to the way it works. I suspect many Mac users would read the above few complaints and try to figure out what I even meant. They don’t miss what I’m used to on Windows because it was never a possibility for them. It’s OK. The Mac isn’t terrible. It’s just different.
We can also debate Apple’s bizarre runaround when it comes to touch. It continues to insist that touch has no place on the Mac’s screen, so it adds gestures everywhere else, to the touchpad, of course, which has gotten ludicrously, pointlessly big on recent Macs. And more recently on the silly and childish touch bar that you can curiously only buy on the most expensive Macs.
Here’s what I know, again, from experience: You may not think you want or need touch, but once you get it, you will use it. You will use it seamlessly and without thinking. And you will miss it when it is gone.
And I miss it when I’m on the Mac. That said, I do like the touchpad-based multitasking gestures that let you switch between open windows using three fingers. But these gestures are not discoverable, you have to learn them. Multitouch is intuitive. Even a child can do it with no learning required. Just saying.
In recent years, it seems like most of the push for the Mac and macOS has shifted from adding iOS features to adding iOS device features. Macs have gotten smaller and thinner, much thinner, and Apple has had to make strange tradeoffs with the keyboard and touchpad to accommodate these new form factors. Apple, for the first time, has gotten vocal and organized push-back from its power users—once its core base, but no more—because devices like Mac Pro and MacBook Pro simply do not meet their needs. It’s been interesting to watch.
But I like the aggressiveness. I like that the MacBook Pro is all USB-C/Thunderbolt 3, that this decision forces people to make the right decisions for themselves and embrace a change that really is better. I know it rankles some. That’s part of the fun.

Recently, I purchased a refurbished 15-inch MacBook Pro in order to replace my aging MacBook Air. The goal here is the same as always, to keep up on what Apple is doing and to do so with hardware that can actually take advantage of all the new features. (You can’t even scale the display on the Air’s woefully-old-fashioned screen, let alone use Touch ID or the touch bar.) And buying refurbished is the only thing that makes sense for me. Apple’s products are simply too expensive.

But the 15-inch MacBook Pro is a bit unwieldy for me, and I may replace it with a 13-inch version instead and save a few hundred dollars. I will deal with that when I get back from my work trip this coming week.
But know this: I will keep trying with the Mac, as I do with any other important personal computing platform. Windows is under assault from all sides these days, and while I do feel that systems like Android, Chromebook/Android, and even iOS may play a bigger role in those battles, the Mac still matters. It would be foolish to ignore it. So I won’t.
I’ll have more to say about modern Macs later this month after I figure out what to do with this latest device.
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