Skateboarding and achilles tendon pain?

A question for all you skating jellies-
About 2 weeks ago every time I skate, or longboard to be more specific, I get a sore pain in the achilles tendon of my left foot (the foot I push with). It could be in my heel, but I’m pretty sure it’s in the tendon. After the first time this happened it hurt to walk, climb stairs, or move it at all so I took a break for 2 weeks. About 5 days ago the pain stopped and so today I decided to give it a try, but at the first push it was back.
I’m not sure if I should skate more because the muscle is weak or take a break for even longer?
Has this happened to anyone else?
Advice would be great.
Thanks guys