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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.
Grado Labs SR80 headphones
A handsfree kit doubles up as headphones for your phone's media, but when you just want to blast out some tunes in your hotel room while writing up your copy, a handsfree kit just doesn't quite cut it. You need something heavy duty and powerful enough to knock you off your chair.
The bass is incredible, the headphones are comfortable, and are not heavy. They come with a 3.5mm jack so they're compatible with the very vast majority of audio devices. If you want a boogie, the cable is long enough to stand back from your laptop and rock out while no-one else is looking.
iPod nano (sixth-generation)
Depending on how long I'm out somewhere -- it can be an overnight job or a few days -- I take my downsized iPod with me for the sole purpose of listening to music when I head out for my morning run. Sure, dismiss the idea as hilarious, but despite my smoke-shattered lungs I still enjoy a good run at daybreak to get the endorphins in the right places for the stressful day ahead.
The iPod is small enough to clip onto my t-shirt and has skip/next-track functionality built into the hardware buttons, making it easy to maintain a good speed while bumping a song for another.
But its in-built fitness app is what separates it out from the rest -- including other, larger iPods (see next). It measures calorie count, run duration and distance through its accelerometer. The online Nike+ service is far from great, but the data can be reviewed in the device's history and added to your own online fitness service.