I agree with poleisnewtome- everything is scary! I feel out of a cross ankle release, and it's taken me AGES to get back to it. I'm still not fully there, but... I've also had some forced time off the pole for a while.
I've got a terrible fear of being upside down, even though most of the pole tricks are upside down... and most of them are things I definitely want to do!
What I do is take them in steps. So, for example, a cross ankle release I will do in reverse from the floor- shimmy my bum up to the pole, lift my hips high, and grip the pole with my legs the way I would be doing in a cross ankle release. If I can then sit up in that position, I know I've got it right, and that it's secure (it's also a crazy good workout for the abs!). Then, after a while, I get into a low pole sit, and get my legs into the correct position. I'll lean back a little bit, and test it out. Over time, I start to let my hands go, sort of like a very difficult, aerial V-sit (it will work your abs like HARDCORE so be warned! It hurts!! Don't do it too much). Once you've gotten used to the grip with your legs, slowly work your way backwards to a full layback. There is a "point of no return," in which you simply have to commit to the layback. It helps to get to this point while low to the ground, because if you can reach the ground with your hands, you then have a great "break" in case your legs slip.
I think that every scary move can be broken down, in one way or another, to make it easier to get used to.
For someone like me, who has an anxiety disorder and is sometimes paralyzed by fear, it can be a great way to push yourself, but not too far. Most people will go through these steps quicker than I will... but, I recognize we all have different challenges.
A crash mat is a really, really good idea, too.
