I am a brave man. I just want to put that out there. Why brave? Because, for no reason other than the sheer testes-shriveling terror of it, I decided to upgrade the operating systems on both my laptop and my smartphone at the same time.
Yes, I did. And I lived to tell about it -- barely. The only thing I think could possibly top this would be upgrading both my laptop and my phone while simultaneously passing through airport security.
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The upgrades: transporting my two-year-old laptop out of Vista Hell and into Windows 7 Valhalla; taking my year-old Motorola Cliq from the paleolithic Android 1.5 to the not-exactly-latest-and-greatest-but-still-more-current-era Android 2.1.
I thought it would be instructive to compare the two results -- and it was, though not in the way I'd assumed.
I've upgraded versions of Windows in the past; I had some idea of what to expect. Thus, I gathered together the necessary materials: Windows 7 Upgrade disc, speakerphone with the Microsoft support number on speed dial; Leatherman tool with a bottle opener, knife, and flashlight; six-pack of beer; bottle of tequila; limes; a shot glass; a comfy pillow; my last will and testament; and, if the worst happened, a cyanide ampule.
Also, a second computer, so I could do the Android upgrade while the Windows upgrade churned ... and churned and churned. The first hour passed, then the second hour. The status bar told me I was still just past the halfway mark; this, I thought, might go on all night.
At some point I must have fallen asleep because I woke up with my head on the pillow, staring at an empty tequila bottle and an error message on my Vista desktop:
Windows could not complete the upgrade. Your old operating system has been restored. Please run the Upgrade Advisor to ensure your system is compatible with Windows 7.
I resisted the urge to take the laptop apart with the Leatherman tool and ran the upgrade adviser, knowing full well what it would tell me: My system was fully compatible with Windows 7. Being not entirely an idiot, I had run the test before deciding to buy the damned upgrade in the first place. (Of course, in typical Microsoft fashion, you have to log onto the Web, click through three pages, and download the friggin' adviser. What, the install DVD was so crammed with Win7 goodness there was no room for another 8MB file?)
There was only one thing to do next: Hit the speed dial and deal with Microsoft Mumbai. I wished there was still some tequila left.
I felt certain the Android upgrade would go more smoothly, and it did. First, T-Mobile had to push down an upgrade to Android 1.6, which it did a few days before making Android 2.1 available. Then it was a matter of downloading a 100MB Zip file containing the new OS to my PC, connecting my phone, dragging the file over to its SIM card, then following some onscreen prompts. I'd have to log back into my old accounts and restore my old apps from the Android Market, but in exchange I'd get a spiffy new(ish) smartphone interface -- easy peasy.