I get asked this question a lot. I somewhat believe in the idea of “if it aint broke, don’t fix it”. However I do feel the need to stay up to date with OS, software and hardware but at the same time avoiding overkill which comes with the risk of being a lab rat. I favor a good balance between staying updated yet not bleeding edge to the point that I’m having to deal with bugs. I can’t afford that lost time in my workflow and productivity. So what do I do? Simple – I stick to the “3rd time’s a charm” rule.
What this means is I wait for the 3rd update to be released then that’s when I make the jump. Why? Because chances are that a lot of the major bugs have been worked out (thank you beta testers – we depend on you). This gives ample time for app developers and software companies to release stable versions of their apps and programs compatible with current iOS or macOS.
You may also sign up for an account at Roaring Apps and add your most important critical apps and programs into your watchlist. Add apps and programs you cannot afford to brick when you install that iOS or macOS update . This gives you a quick list of apps and programs you can always reference to and easily determine if those programs and versions that you have are compatible with the iOS or macOS you intend to upgrade to. You can set your account to notify you of compatibility updates as well.
Wait! Plan And Make Preparations Before Installing the Update.
Backup that iPhone in iTunes. This is so easy there is no excuse. At least if something goes wrong or if you’re not happy with the iOS update then you can always do a restore.
Once you’ve made the decision to update your OS, at the very least, use Time Machine to back up your computer which is already baked into macOS since Leopard. This will give you a chance to recover your entire system from the Time Machine Backup. Additionally you can create a bootable backup using Carbon Copy Cloner or SuperDuper!. Should anything go wrong you can quickly boot from that backup and avoid the restore process that Time Machine makes you go through. You’ll be up and running in no time. Do both if you can but if you can’t – at least set up Tme Machine.
When do I know the 3rd update is released?
Checking your iOS general settings or macOS App Store’s Updates section is not going to cut it since we’re specifically seeking for the 3rd release as our go signal to go ahead and update. You can look for the table of versions/release history in Wikipedia:
macOS (jump to the latest OS link and a table of release history should be there)
Alternatively you can check out MacRumors – they keep awesome track of the various updates released for both iOS and macOS.
3rd update release – that’s when I recommend to update. This may be very conservative to some but I feel it’s a good balance between stability and keeping updated with minimal risk to breaking your workflow and productivity.
Additional reading: Should you upgrade at all? – Specific to El Capitan but I feel presents concepts relevant to any OS upgrade. Good read.