When I updated my phone to iOS 7 a few weeks ago, I was a little concerned. I know enough to know that you should never, ever, be an early adopter. But I’ve always been a maverick, so I went for it.

After a couple of days, I updated my iPad, too. In both cases, I hesitated over the “update apps automatically” setting. I know enough to know that sometimes an update isn’t an improvement, and (especially with iOS 7), you can’t go back again. But I’ve always been a maverick.

Those Pro Tools guys used to make me smile, with their oh-so-slow adoption of and support for new operating systems. I used to work with a designer who persisted with Quark XPress 3.1 while the world moved on through versions 4 and 5….

When Apple announced Mavericks was a free download to supported machines, I thought about it. I thought about the various Macs in my classroom and their different-generation operating systems and saw an opportunity to bring things into line. I thought, I’ll install on my MacBook first, see how it goes. The wise old power user inside of me protested. Wait for the .1 update, he said. Then see how it goes. But I’ve always been a maverick.

I should have backed everything up first, but that takes soooooooo long. I’ve used Time Machine in the past, and as far as I could tell, it seemed to be designed to just fill up hard drives..in any event, I only backed up documents and not the system and apps, figuring I would just install those from scratch should the need ever arise.

So I was a fool. And then several things seem to have combined to make my life (especially my job) very difficult. First of all, Mavericks wouldn’t install. It reported a damaged hard drive, and threw a wobbler about 75% of the way through the process. Having done that, my Mac was non-functional, because the previous system was gone. Kernel panic after kernel panic, as I tried to restore. So I had to spend the day trying to get the hard drive to even mount so it could be I mounted and erased. I plugged it in in target disk mode and ran disk first aid. Half an hour later, it was at least visible. I then copied as many of my files as I could. That took all afternoon.

In the evening, I reinstalled Mountain Lion, an operating system I had hoped to see the back of. When was the last good one? Snow Leopard? I had the disk, but the computer wouldn’t let me install it. Instead, it downloaded ML from the App Store. As a matter of urgency, for lesson 1 today, I needed Keynote and Pages. Tried copying the files from another Mac. No.

Meanwhile, I realised, too late, that my iPad versions of these apps had already updated to the iOS 7 versions, which will only synch with the Mavericks versions. So my cloud versions of the files, if opened on the iPad, would no longer work on the Mac, even if I could get iWork working again.

This morning, reinstalled iWork from the original disk. Twice. And downloaded the updates. And rebooted into Safe Mode. Twice. And repaired permissions. Twice.

And so?

“An unexpected error has occurred. Please quit and reopen Keynote.”

I’ve always been a maverick.