what i used to do is practice in grass or carpet right before u do it on conrete to get ur confidence up. then, move to a sidewalk that has grass on both sides. so when u fall, ull probly land in the grass..
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Seems to be a hard question to answer, sense It is personal. To overcome your fear, Just go for it. Think how awesome it would be to do tricks like the pro's. Do beginner tricks first, Like ollies and kickflips. They you can progress to better,and better tricks
here's an excellent tip to not be afraid of doing an ollie, do an ollie in the grass first, or on a trampoline. :) please give me a trust point.
There is no way to do it purposfully. It subconsiously comes with age or maturity. I would suggest just doing it. Forget fear just go for it.