wear a beanie or whatever and keep doing headspin BUT.. instead of just falling try to catch yourself so like (headspin) *catch with handss* (headspin) *catch with hands* and keep doing that over and over so like sooner or later you'll have like 15400841651871 headspins =D
Drilling is where ou are just spinning on your head only after pushing off once with your hands and incresing your rotation speed so that you are like a drill with your head "drilling" into the ground.
I am not confident because i have anything you don't. I'm confident and assured because i'm doing all the things i thought i couldn't do before. - Desi Boogie
try to get down the tapping motion(using ur hands to catch urself to prevent losing balance while headspinning) of the headspin, this will help to keep u upright while spinning. after that try to work on kicking to get momentum, just experiment on w/e way ur comfortable.