macOS High Sierra and The Great Purge

Apple’s incessant nagging gets to me. They really seem to want to grab your attention with alerts and updates to a level that reminds me of Microsoft Windows of the early-to-mid 2000s. This is perhaps no more true than with OS updates. I do my best to resist them, but in a moment of fatigue and weakness after busy few days around New York, I gave in and allowed them to update my laptop to macOS High Sierra. After all, I had no trouble at all installing any of the previous mountain-themed updates (Yosemite, El Capitan, Sierra), and maybe I would even save a little disk space on my boot drive afterward.

This was a huge mistake. After several minutes of churning — harmless enough — it stopped with the ominous message “macOS could not be installed on your computer.” Unfortunate, but ok, just move on. But after rebooting and attempting to log in, I started getting Linux-style text errors pouring down the screen and a kernel panic. This repeated multiple times and was definitely not good. Not good at all. A boot to recovery mode with Command+R and running “First Aid” in Disk Utility cleared up that problem, but I now had a MacBook Pro stuck in a Groundhog-Day-like cycle of attempting to install macOS and failing.

OK, no need to panic yet. After all, I could restore from Time Machine back in San Francisco. But in the meantime, no CatSynth posts with photos, no CatSynth TV episodes, no app updates. And when I want to get something done, I really want to get it done. Perhaps, in retrospect, it is this impatience that gets me into situations like this.

My best theory as to what went wrong (none of the obvious things via Google search made any difference) is that the macOS installation collided with the older Journaled+Encrypted hard drive, or perhaps the 40GB of disk space was distributed in such a way that hindered installation. So before and after a delightful Thanksgiving with family, I embarked on another direction: making a quick backup image of the still intact drive, and reformat it in a more modern but unencrypted way. Both those operations went smoothly, and macOS High Sierra installed quickly and flawlessly afterward.

But now I had a blank system. I realized rather than tragedy, this is actually an opportunity. The filesystem was basically layers upon layers dating back to at least 2011, a mess of disorganized photos, music, scattered source code and partially uninstalled applications. It was always on the verge of running out of space and running rather slowly. I now had a chance to start again, without losing what I had in the past. I have done such a purge before, but not in several years — I have been lulled into complacency by installations and backups that mostly work. So we are now installing our most used items: Photoshop, Lightroom, Final Cut, Xcode, IntelliJ, etc. The music is simple. I’ll figure out what to do with the photos. And I’ll leave the old image on an external drive.

We are starting fresh, or fresh enough. And while it will be a day or two before I can do videos again, we can certainly get back to more articles; and sort the rest out when we get back to San Francisco. It’s also an observation that in-the-moment impatience is sometimes a blind spot. I need to pause a bit more, perhaps, even in those moments when I don’t plan to.