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.
[ Check out Cringely's biggest tech turkeys of 2010. | Get the spin on key tech news that you'll find nowhere else at InfoWorld's Tech Watch blog. | For a humorous take on the tech industry's shenanigans, subscribe to Robert X. Cringely's Notes from the Underground newsletter. ]
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.
The upgrade from 1.5 to 1.6 had a few hiccups; for example, it wiped out my speed-dial list (apparently, I'm not the only person who's had this experience). Otherwise, it was fine. The combination of Android 2.1 and the MotoBlur interface crap T-Mobile shoveled onto my phone, however, was a nightmare from which I am still trying to awake.
My speed-dial list was intact, but it took forever to load -- like over a minute, as did my list of recent calls, when it loaded at all. Not to mention my contacts list -- tapping on a name or number sometimes would call that number, sometimes it would call the next number on my list, and sometimes it would do nothing at all. The same thing happened when trying to swipe between screens or run other apps; the phone would lock up or reboot inexplicably. In short, my Android phone was acting suspiciously like -- that's right, a certain operating system made by you know who, circa 1989.
When I called T-Mobile's friendly tech support line and described the problems, the woman on the other end (at T-Mobile, it's always a woman) acknowledged that they'd heard them before. This was "a known issue," I was told, and T-Mobile planned no more upgrades to my phone -- in other words, don't expect a fix. My options: Reinstall Android 2.1 and hope I got luckier this time; downgrade to Android 1.5; or send in my unit for a replacement, hoping it was somehow a hardware issue.
I opted for redoing the install. Everything worked OK for a while, then the same problems returned. Now I have a smartphone that's dumber than a toaster -- nice.
Back to Windows
I steeled myself for a long, ugly call with Microsoft support, filled with endless holds, a lot of repeating myself slowly and cursing, and an argument over who was going to pay for this call. Instead, after a few minutes where some interstitial operator determined that yes, I qualified for free installation support, the exceedingly polite and articulate Jamie came on the line.
Jamie walked me through the upgrade again, but instead of choosing the Upgrade option, which preserves all my installed programs, data, settings, and so on, Jamie told me to choose Custom. This would wipe the OS and apps, but keep my personal files in a folder on my hard drive. What choice did I have? I chose Custom. If all went well, Jamie said it would take about half an hour. He promised to call back in an hour to make sure I was still breathing.
Amazingly, it worked. About 45 minutes later, I was staring at a Windows 7 welcome screen. None of my favorite apps were there, but all my data was waiting for me. Here's the best part: My computer was no longer a mastodon trapped in the tar pits, barely able to navigate its girth from one task to the next without locking up entirely. It was more like a rhino charging through the veldt -- not exactly sleek, but a whole lot better than before.
Right on time, Jamie called. I told him the good news: Windows 7 is the upgrade Vista should have been. It's not perfect by any stretch, but I'm no longer on the verge of tossing my laptop off the top of a 10-story building.
My Android phone, on the other hand? I'm deeply regretting that decision, along with my two-year contract with T-Mobile. Those new Verizon phones look pretty tempting.
Has this made me a convert to Camp Microsoft? Hardly. It does raise my opinion of the post-Gates crew, however. Somebody somewhere knew what Vista broke and how to fix it -- give them credit for that. As for Android, my faith in Google, already shaken by various and sundry events this year, takes another hit. It may soon be the leading mobile OS in terms of sheer numbers, but it's clearly not the Great Geek Hope it was made out to be.
How about you? Email me your upgrade horror stories and/or tales of wonder: firstname.lastname@example.org.