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Why You Should Upgrade (On Your Own Terms)

We’re heading into Apple’s annual upgrade season again, with the upcoming releases of OS X 10.11 El Capitan, iOS 9, and watchOS 2, along with innumerable associated apps. Every upgrade is touted as the next best thing, teasing us with hot new features and promising improved performance, reliability, and security.

Unfortunately, these constant upgrades fill many people with dread, or if that’s overstating the case, with weary resignation. As the saying goes, if it ain’t broke, don’t fix it, but most changes foisted on us by technology companies are no longer aimed at fixing bugs or making everyday usage easier. Bugs are fixed, certainly, and security vulnerabilities blocked, but those under-the-hood improvements are part and parcel with checklist features from the perky twenty-somethings in Marketing and whatever visual tweaks were deemed trendy by the hipsters in Design.

I know many of you are tempted to scream, “Stop this bus! I want to get off!” And many people did just that some years back when the misbegotten OS X 10.7 Lion was on offer — there’s a vocal group still happily (or at least defensively) using 10.6 Snow Leopard. There’s probably still a set of iOS 6 users holding out against the flat look of iOS 7 and iOS 8 too. None of you are wrong. You may be merely postponing a world of upgrade hurt, but you’re not wrong.

Here’s why, and this is the great chasm that separates Silicon Valley from the real world: different is not better. For many, different is by definition worse. We are finite beings, living finite lives. We should never turn down an opportunity to learn — that’s the secret to eternal youth — but there’s a distinction between learning more about our role in the universe and figuring out where some previously obvious interface control has been hidden. iTunes updates alone over the past few years may have cost society millions of wasted hours.

Plus, we become attached to the things in our lives. We build relationships, not just with people, but with our environments. I’m no psychologist, but the emotion I most commonly see in response to changes forced on users by the tech industry is anger. How would you react if you got in your car one day and all the buttons were in a different layout, with dark grey on black labels? “That’s the new look,” you’re told, “You’ll love it. In addition, your gas mileage is now 10 percent better and hackers can no longer take control of your car remotely. Oh, and we’ve decided that the steering wheel should be polished aluminum and the brake pedal should move a few inches to the left so it lines up better visually. Really, you’ll love it.” Sure, all that might happen if you buy a new car, but that’s your decision. When you have little or no choice but to accept unwanted changes, a bout of anger is entirely understandable.

The reason all this is happening is that your opinions don’t matter once you’re a customer. The tech giants are competing purely for new customers, and doing so with features and interfaces that cause those moving from a crusty PC or a flip phone to go “Ooo, shiny!” But the real catch is that each one is trying to lure you into a closed ecosystem, and once you buy in, whether we’re talking about Apple, Microsoft, Google, or Amazon, you’ll be captive in a walled garden. Better hope the fruit is tasty, because it’s hard to scale the wall, and all that’s on the other side is another walled garden.

So yeah, I hear your frustration and I understand your anger. You’re not wrong. But, as much as it pains me to say this, you probably can’t opt out. You have to upgrade, and you have to do so at least semi-regularly, if any of the following would affect you:

  • New hardware is inevitable. Macs and even iOS devices can run for years, but eventually you’ll want or need to buy something new. That’s not inherently a problem — it can just be new — but the greater the generational difference, the harder it will be to bring old data and apps forward. I just heard from someone who is having trouble migrating his iPhoto library to Photos on a new Mac because he hadn’t kept up with iPhoto updates; hopefully the iPhoto Library Upgrader will do the trick.
  • Community knowledge and technology tools fade away. The iPhoto-to-Photos conversion story above is a perfect example of this problem — the guy in question had gone to an Apple Store for help, but wasn’t told about that older utility, and even I didn’t think about it until I was writing this article. I’ve also seen this happen with people who postpone switching away from Eudora — the longer you wait, the harder conversion utilities are to find and the less those of us who knew a lot about Eudora remember (that’s why I wrote “Converting Email from Eudora: Why I No Longer Live at the P.O.,” 6 September 2011). The more time passes, the harder the upgrade will be, perhaps even to the point of losing data in an unsupported program.
  • No Mac is an island. Actually, at this point, it’s far more likely that someone would have an iPhone but not a Mac, or any other computer at all. But if you do have multiple devices, keeping them working together fluidly often requires upgrading them all regularly. And a single decision can lead to a chain reaction of upgrades. Imagine that you have an iMac running 10.6 Snow Leopard and an iPhone 4S with iOS 6, and you receive an Apple Watch as a gift. Suddenly you need to buy a new iPhone running iOS 8, and you’ll need to upgrade at least iTunes, and likely jump from 10.6 Snow Leopard to 10.10 Yosemite to take advantage of iCloud (which requires at least 10.7.2 Lion — I wrote about this catch nearly four years ago in “Apple’s Planned Obsolescence Schedule,” 2 November 2011).
  • New and upgraded apps stop being available. This isn’t obvious to normal users, but Apple introduces new and highly attractive options for developers with every new operating system. That’s great, but puts developers in the uncomfortable position of having to maintain both old and new code to retain backward compatibility. Keeping apps compatible with older operating systems is a difficult business decision, particularly for a small developer. So getting off the upgrade bus can prevent you from taking advantage not just of new apps, but also of useful upgrades to apps you already rely on. (This is why we always list the minimum operating system requirements in TidBITS Watchlist articles about Mac app updates.)
  • Security vulnerabilities remain unpatched. Apple continues to release security updates for two operating system versions before the current one, but pushes the last one off the bus with every upgrade. So, 10.8 Mountain Lion users, prepare to tuck and roll with the release of OS X 10.11 El Capitan, since you’ll never see another security update. Personally, even though my security-conscious friends might disagree with me, I think the danger of running older versions of OS X is overrated. Yes, older, unpatched systems are vulnerable to known exploits. But at least in the Mac world, they’re also in the minority and are thus less likely to be targeted by evil software than more common operating system versions.
  • Technology makes life better. This is the kicker — alongside the nonstop releases of worthless upgrades that add pointless features or revamp an interface just to look hip, there are technological advances that truly improve our lives. We would be far poorer without today’s Macs, iPhones, and iPads. And it’s equally hard to imagine life without Google’s search engine, without Amazon’s massive online store, without Netflix’s vast library of TV and movies, without Facebook for bringing friends and families closer, without Skype video calls to far-flung relatives, without PayPal’s easy online payments, and goodness knows what else. For better or worse, constant change is implicit in the tech world, and opting out of
    upgrades makes it hard to benefit from the life-changing bits.

I’m not saying that you should drop everything to upgrade as soon as Software Update alerts you to the latest and greatest. In fact, apart from certain security-related updates that would be good to get sooner rather than later, I think waiting a decent amount of time before upgrading makes a ton of sense. Immediate upgrades are for those of us whose business revolves around the latest details — we’re the penguins diving off the ice floe first so the rest of you can jump in without worrying about leopard seals. Wait a bit after a major upgrade, and for a minor update or two to address bugs that became obvious only after widespread public release. We may have early-bird releases of “Take Control of Upgrading to El Capitan” and “El Capitan: A Take Control Crash Course” available now, with updates planed for El Capitan’s release day, but we also continue to refine those books after launch.

So wait if you want, but don’t wait too long. Community knowledge doesn’t go back that far any more — there’s just too much to know, and too many facts that quickly stop being relevant. Options disappear too — drag your feet on upgrading to the mature Yosemite now, and in a month or so, Apple will replace it with El Capitan, and you won’t be able to download a fresh copy of Yosemite, just as you can no longer get a new copy of Mavericks from the Mac App Store. (And yes, people are still getting “Take Control of Upgrading to Yosemite” for just this reason.)

In short, take a deep breath, relax, and go with the upgrades. But do so intentionally, and on your own terms.

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