When it comes to distance running, I break things into 3 phases:
- Running1 - Songs to kick start your run early in the morning and get you going. Upbeat songs that might lean towards having a long lead in. Think "Rock and Roll Ain't Noise Polution" by AC/DC or "Knocked Up" by Kings of Leon.
- Running2 - I use these playlists when running half marathons and marathons and my secret to a good long run is keeping a good pace in the middle of the race. These songs tend to have a nice groove and often end up being the highlight of my run. Think "Use Me" by Bill Withers or "Covered in Rain" by John Mayer (what was once my most played song ever).
- Running3 - Now that Running2 has effectively saved you from burning out at Mile 20, these are the drop dead adrenaline songs that are gonna bring you into the finish. Think "See Through Head" by The Hives or "Positive Tension" by Bloc Party.
So use the comments field in iTunes to label your songs as Running1, Running2 or Running3 according to the rules above and you'll have laid the ground work.
Now time to load the playlist. I like to be surprised by what's coming on next on my run, but obviously not totally surprised (I mean, we can't have a Running3 at the beginning of the run - am I RIGHT!?!?). So to load your playlist, first figure out how long you're going to be running for - let's say 2 hours. Divid the time into thirds (ish) - let's say 45 minutes for each third. Then set up 1 playlist to randomly pull 45 minutes of Running1, another playlist to pull 45 minutes of Running2, and another to pull 45 minutes of Running3.
Load all three of these playlists into one final playlist in order (so all the Running1s are first, Running2s are second, etc.) and voila!
You now have a random (and yet predictable) set of tunes that are going to pump you up, set your pace and let you finish strong (TWSS).
For example, here's what my system just spit out for tomorrow's Aspen Half Marathon:
Easy, right? What? I have too much time on my hands. Okay, fine. Ruin my fun.