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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.
hats-
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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The fella I was talking to is John Kew - he doesn't seem to be in the club, but is probably pretty well known in the circles.
hats - you could work this counterintuitively and just knock out a long slow 30 miler in training - then you know you can do it come race day.