#1-------------------- If you are wearing lifts in your shoes permanently, you are alleviating the pain. But, you are also "teaching" your achilles and soleus to get used to a shortened position... which in the long run, may only make you more prone to injury (as a corollary, women should avoid high heels). I wore a heel cup that cushioned my heel for about a month - but only during the day, and never when I ran.
Insert comment from Scott: Yes, but I would wear a heel lift if it relieves pain. This allows the heel to heal. It is a temporary measure. I think keeping up stretching activities will prevent the inflexibility that could result from using heel lifts.
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