A couple of weeks ago, I had a rude awakening to one of the ways in which giant corporations control our access to information.

This week, I’ve had a similarly distressing introduction to the havoc a tiny font can wreak.

I’ll admit that I’ve been somewhat of a pack-rat when it comes to fonts. At one point I had over 2,000 of the little buggers installed. Among my collection, I’d amassed dingbats in the shapes of skulls, 3D daggers, and more than a dozen pirate fonts with names like Arrr Matey and Black Sam’s Gold. (What can I say? Johnny Depp made piracy look so good.)

A few weeks ago, I decided to upgrade my Mac to Snow Leopard. The elegant new operating system wouldn’t support some of the older font formats, so hundreds of my more festive buddies would have to go.

I gritted my teeth one September day and pared my collection down to about 600 of my most trusty workhorse fonts. I installed Snow Leopard, got back 9 gigs of space on my hard drive, and was happy as a clam.

The only hiccup was that Microsoft Word was taking longer and longer to launch. “Optimizing font menu performance,” it would say on every startup. Optimizing, still optimizing, even more optimizing … until last Sunday, the program stopped responding altogether.

I ran a quick test on my fonts and found that two of them were corrupt. “Into the trash with ye mutinous little bilge rats,” I said. But the Microsoft gods were not appeased. I continued sacrificing suspect fonts—starting with a few at a time, and then trashing entire collections—until I had only 300 fonts left, but still Word would not launch.

I turned to The Internets for guidance and found that others were reporting a similar problem after their upgrade. So I followed their advice and cleared my caches and deleted my plists and validated my fonts and rebooted and safe booted and wiped and reinstalled. I spent $160 on the newest version of Microsoft Office 2008. I again cleared my caches and deleted my plists and validated my fonts and rebooted and safe booted and wiped and reinstalled, all to no avail.

Finally, in despair, I paid a visit to “Mike The Genius” at the Ridgedale Apple store. In spite of watching his every move intently, I have no idea what voodoo he performed. But Microsoft is again behaving.

The funny irony is that yesterday Mike asked whether I’d considered trying iWork ’09. It can open Microsoft documents—and resave them as such—and it’s designed to work with my operating system. If only I’d known that $160 ago. Oh, well. I picked up a copy anyway, in case Mike’s fixes don’t hold.

I’ve gleaned two big lessons from this sad tale. No, make that three lessons:

1) Never upgrade your operating system on the first release. I usually follow this rule with all new technology, but somehow I fooled myself into thinking that Snow Leopard was a “refinement,” rather than a whole new ball of code. My bad.

2) If at first you don’t succeed, try again, and then give up. If only I’d visited the Genius Bar last weekend when the problem first became evident, I could have saved myself 40 hours, eight tension headaches and an ulcer.

3) Always have a backup plan. It’s easy to take for granted how much we rely on technology until it fails us. The past week has served as a great reminder of the importance of contingency plans.

Here’s a big thanks to Mike.