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BlackBerry Bold 9790
My iPhone escapades on a February trip to New York and San Francisco was far from a fruitful endeavor; I ended up spending more than four-times on the cost of data (along with the cost of the iPhone itself) which left me almost $2,000 down in the space of a fortnight.
Email is my primary motivation for keeping my BlackBerry, with data compression and a physical keyboard second and third. It churns through only a fraction of my monthly data tariff, and the mini-keyboard means my MacBook, which would normally be used to write emails, can stay in my bag conserving power. Above all else, phones are for talking with: I've never known call quality to be so good. Many callers thought I was permanently in a tunnel or a bathroom with the amount of echo my iPhone kicked off when I had it.
Plus (see later) for encrypted emails, a BlackBerry is a must. You never know which government's are looking in, and when dealing with occasional matters of political importance, it's better to be safe (and paranoid) than not.
Sometimes the most important piece of kit doesn't have a screen, light up, play music, or connect to the Web. It's the bits in-between devices that keep everything ticking over. Without this tiny cable I wouldn't be able to connect my devices together.
That's it. It doesn't need a song and dance about it because that's all it does -- but I would be lost without it.
BlackBerry Wired Stereo Headset
Simplicity is key to being on the road. The single reason why I keep a handsfree kit with me is so I can avoid pinning my phone to my shoulder as I type because my right-arm starts to goes numb after a few seconds. (I'm not kidding. I know -- it's probably something I should get "checked out.")
A handsfree headset is a plug-and-play kit without pairing, interference or worries about battery, unlike Bluetooth alternatives. It's no myth that men can't multitask but there are times where you have to bring in an often unthought-of piece of technology to bridge that gap.