Our expert says:
The pain is probably caused by stiffness of the tendon, and that's why it hurts in the mornings and after a period of being immobilised when you are sitting for long. So, it's when the tendon is being held in a certain position for a long time - the exact cause I would be guessing at, but it's a good sign that it is not hurting you during the exercise sessions, or at least that is what I gather from your email. What I would suggest is that you stretch that tendon very well, particularly before the session. The stiffness might be caused by very tiny, 'microscopic' tears in the muscle or in the tendon itself, and possibly some scar tissue around the tendon from a previous injury. This might be the cause of the pain, and so regular stretching, and a little self-massage may be all it takes. Then the best thing to do for this is a one legged heel raise - find a step, at least 10 cm in height and just stand on this step with your heel hanging over the edge, and then raise your body up and down using the calf muscle - this will cause a 'burn' in the calf muscle - don't overdo this, just do 10 reps on each leg, three times a day. This is a great way to strengthen the tendon.
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