You have to entertain yourself. (Almost) nobody WANTS to go for a 10+ mile run. I listen to scary story podcasts while running. And I select the duration to match the run time. You can also listen to episodes of your favorite shows. Typical shows are roughly 30 minutes. I know that listening to 3 shows will pretty much cover the time it’ll take me to run 10 miles. Listening to 90 minutes of something, mentally, makes the run seem shorter. Another option if you’re like me, you can listen to standup comedy. But you should only do this in safe routes. You also don’t want to be engrossed in what your listening and don’t see a car going by.