if you've only been skating for 3 months, maybe you just need to chill out and stop trying to do tricks for the time being, or at least the ones you are trying. skating certainly involves doing ollies, but it also involves having fun and it sounds like you're not really having any fun - just stressing over fear and pain. from how awkward it sounds for you - i think you should stop using your cruiser board and just push around, tic tac, crabwalk and carve and learn how to let your body be loose on a regular skateboard.
also, there is no real connection between being able to do something holding onto a railing and doing it without the railing, so i wouldn't consider that an inconsistency in your ability to skate - it's just that they're two completely different things.
and yeah, you do need to learn to enjoy/harness the fear and pain. everybody has it and is kind of a big part of what makes skating a thrill. but that's all up to you to wrap your head around - don't buck at it when people tell you it's part of skating - it's not macho, it's just a fact. i'm certainly not a macho man.
what sort of skating do you aspire to?
have fun!
I split my skating into 2 activities, cruising and flat ground practice.
I've only been practicing 3 tricks, ollie, manual and shove it.
I stopped practicing the shove it when it made me realize that regardless of how "comfortable" I THINK I am riding my board I still have a long way to actually being it.
Cruising around fast and being able to carve for speed and to reduce it is one thing.
I'm now practicing riding off curbs and doing front and back side pivots...reverts in the odd circumstance i encounter smooth concrete (rare) I'm also focusing on manuals though I'm afraid they're going to ruin my deck before i can learn to do much else on it...
I've come a long way since this posts creation.
I'm actually able to attempt and often land an ollie while rolling!
Aspirations?
Funny you say that, originally I wanted to learn downhill freeride...lol yeah I live in south fl...
So believe it or not, what got me interested in skating was wanting to be able to power slide giant hills...
But once I realized that would be impossible unless I moved...
I decided to simply learn basic street skating, how to ollie up and off curbs and be able to stop by powersliding...and SLAPPY skating...that looks really fun...