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Running is a very personal thing- so my opinion/ advice should be taking with a massive pinch of salt.
I'd ditch the tech completely- when I used to run with music/ audiobook/ podcasts- I found that if they got too interesting/ boring/ slow I fell out of my natural running rhythm. And though its difficult weaning yourself off them for the initial few runs- the reward in headspace is amazing. I reckon this was one of the 3 or 4 things that made me enjoy running.
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Half agree half disagree - I found podcasts for long slow runs a great help to distract, especially if the distance is the thing you're having trouble with. Couldn't listen to them for intervals or hard runs though. And never music but that's just because I find it has an artificial effect on my pace.
5awyr
I think this is what I'm going to try. Get some podcasts lined up, pockets full of snacks and then set off for a long day. Then at least I won't be so scared of the mileage and can be scared of other things instead.