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RE: Can I break 5 in mile?
Probably, but you should go run a mile and report back. That would give you more info and a great baseline starting point.

Random Musing: 30 years ago I never would have thought to ask someone if they thought I could run a certain time. We just gave it a shot and checked the clock. Now we go on the internet.

I can see asking the question about a longer distance, like a marathon or half. For anything like a 10k or shorter, just go knock it out when you're well rested and end the speculation. Sometimes the simplest approach is the right approach.

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