“Thanks for your patience Mr. Pasternack, I mean, Jeff. I suppose its better than a poke in the eye with a sharp stick, eh?”

My jaw went slack as I tried to process how my experience with the T-Mobile Sidekick could have been worse than a poke in the eye with a sharp stick. Come to think of it, there’s not much that’s worse than that. Is a poke in the eye with a blunt stick better? Certainly, receiving a jab to the ribs from a sharp elbow at 3am ranks right up there with the poke in the eye. But I digress. Let me start from the beginning.

The business problem I am still trying to solve is how to reduce the number of gadgets I carry around. Specifically, I want to find a phone with Palm Pilot-type capabilities. I don’t want to deal with the stylus and having to learn a new written language, which means I’m destined to use one of the models with a keyboard. Of those with phones, I’m left with the Handspring Treo 270/300 ($450), the Blackberry 6510 ($500) and the T-Mobile sidekick ($250).

Personally, I think the Treo 270/300 is pretty nifty, although I am pensive about the clamshell design, which seems a bit flimsy. The good news is that, after dialing, the phone can still be used with the lid closed and this reduces the risk of it snapping off when it falls off the front seat of my car. I can also keep my Sprint account and not have to learn a whole new area for where calls are going to be dropped. Finally, it also integrates with Outlook, Act and other programs as it uses the Palm operating system. The buttons are a bit small and slippery, but workable. And while $450 is the list price, it could be bought on Amazon for about $306, thanks to two rebates and a special trick embedded in a click stream.

The Blackberry 6510 runs on Nextel, so you can get the whole direct connect chirpy sound thingy going. There’s no lid to deal with and it has powerful integration capabilities for accessing databases from the road. Hands down, it is the most advanced unit and, in my opinion, is best suited for bigger organizations that can make use of its integration capabilities.

Which leads me to this really nifty thing called Sidekick. Made by Danger and supported by T-Mobile, it has a unique display mechanism. Instead of the ubiquitous clamshell design, the Sidekick’s screen swivels over the keyboard, and the unit can be used open or closed. It has an email application, AOL Instant Messenger and some other typical tools, but it doesn’t integrate or synchronize with any desktop applications at this time. Instead, to load in a phone book, one must do so by uploading a text file using the T-Mobile Web site, and even that process is rumored to be clunky. Note that the key word in the last sentence is “rumored.”

After reviewing my options, I bought the Sidekick at the end of December. At the time there was a $50 rebate. Of course, by February 13, it was free on Amazon.com if you signed up for a new T-Mobile account. Amazing how a $250 device is given away for free just for signing up for service, eh?

The purchase process took an hour at the T-Mobile shop as the staff, which knew little about the unit, fumbled through the process. Questions about integration were hesitantly answered and it was decided that the best way to upload my phone book was to save it as a text file and bring it to the store, where they would upload it to a Pocket PC with my Sidekick’s smart card inside. Once loaded, they’d put my card in my Sidekick and the data would be transferred over. My skeptical smile got the better of the staff and a manager in another store was called. He said that I should upload the file to the T-Mobile Web site and that I’d have to wait a day or two to do that.

Blinded by a false sense of salvation, I ran home and began playing with the Sidekick. It was really, really neat. The keyboard took about 30 minutes to feel comfortable and the thumb wheel helps with the navigation process. All the loaded applications worked as expected and I was easily able to change the ringer tone. I can neither confirm nor deny that the ringer tone I selected resembled that of a 1970’s porn soundtrack. As I use a headset 90 percent of the time, I was happy to ignore the unit’s awkward fit against the ear.

I set out the next day, armed with my new convergence device and the delusion that my days as a TechnoPeasant might finally be done: with a single device, I would advance to the rank Technocrat! Could the lofty title of Digerati be all that far ahead? And yet, there was a nagging fear of what I always know to be an unyielding truth: I am Charlie Brown and the technology industry is Lucy. I’m going to end up on my back, again.

My first stop was DC’s fine mass transit system, where my phones have never worked and neither does Sidekick. Lacking expectations, I wasn’t fazed and I played Tetris whilst my fellow passengers gloomily glared at me from the corners of their jealous eyes. I emerged at the Regan Building and thought I’d send a quick IM to an employee. Naturally, I thought wrong. There was no service in that area, or anywhere else in easy walking distance, either. Bummer. Later that day I returned to Rockville and used the phone with no problems…until I visited a client in Cabin John, where service vanished. The next day I had service on the Dulles Toll Road, but not in Reston. Connectivity, it seemed, was very spotty. I also couldn’t log into the T-Mobile Web site.

Four days later, I was still unable to login to the Web site and the number of no-service areas was growing more numerous than Sprint’s. Twelve days and four phone calls to customer service later, I admitted defeat. I trudged back into the T-Mobile dealer, where I spent yet another hour on the phone with customer support. I explained the problem with not being able to login to the Web site and described the areas where I had no service. My closing sentence to the service representative on the phone was: “Well, it was a nice try, I guess…kinda disappointed that the whole thing with T-Mobile didn’t work out.”

And you already know the response that elicited.