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800 dude
RE: At what point of a 10k race should one really be hurting really bad?
No good answer here. 10k is long enough that you can enter and exit rough patches. You can be hurting bad at 3 miles, hold the same pace, and suddenly feel better at 4. I think it's because so much of the 10k's pain is about the mismatch between how you feel and how you think you should feel. I always feel pretty darn good at 5 miles because that's when I realize that I'm going to get to kicking range with at least a little something left. At three miles, it's easy to start thinking that there's no way you can go twice as far again at the same pace, and that doubt has the effect of amplifying your pain.

In the 5k, by contrast, I don't think the expectations play as much of a role. The race is characterized by a steady buildup of oxygen debt that gets pretty serious by the end, but in the middle of a 5k, everyone should be feeling pretty darned good.

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