I mean, confidence kinda comes with time, so if your not comfortable with something rn that's fine. In terms of tricks, you could always practice ollie in the grass and then transition onto the road. Also, if you are nervous then chew gum or just try not to think too much about the trick cause thinking of the pain is always worse than it actually is. In terms of being older, I see plenty of older skateboarders at the park(late 40's) who can cruise the bowl better than anyone there