One of the reasons for fear is not knowing how much of a repurcussion there is for crashing and burning. Will you be in traction for the rest of your life? Paralyzed? Or just embarrassed?
I've found that most of the time, the consequences are much lower than what you'd think from watching a bail. Mind you, that's downhilling or jumps. As soon as metal or wooden features are involved, that can change.
The easiest way for me is to incrementally increase the risk, so you desensitize yourself to a level of risk before upping your game. How you do that depends on what you're doing.
50-50's on a feature are relatively safe. boardslides, not so much. If I ever get to the point of wanting to do boardslides, I'm going to initally armour up like a motocross rider, including face protection, and I don't give a damn if I look like a dork. I'd rather look silly than end up having dinner through a straw for a couple of months.
Cant imagine boardsliding without padded shorts.