I ware my Ipod all the time. Here in Los Altos on Foothill Expressway it is straight with a nice shoulder for bikes. I know how fast or in this case slow I am so I stay to the left unless it is uneven in which case I am more to the right for a stretch. I crank the tunes and push my HR up. It is sort of a motivation, as last week I did 15 miles at an average pace of 17.6 which is new for me. I am always looking around and haven't had issues. I don't crank it either so I can hear folks letting me know they are passing. The less people that pass the better I know I am getting.