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You can start with intervals (Gymboss makes an interval timer that beeps or vibrates). Start with intervals running 30s and walking for 1 min for 20 mins and build from there. Some marathoners go 26 miles using this technique.
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Any kind of buds with rubber tips that fit inside the ears. I find them for $4 - $6 at Ross. I hate the giant metal satellite dishes that come with iPods.