Me learning skateboarding "no I'm scared of breaking my ankle when I fail".

Wtf is wrong with you. Dude fell like 20ft, no matter how professional you are at things you will still make mistakes, he broke his leg from a fall not from being old, he had a mistake because he is human not because he is washed up. I bet you don't even come close to his skill level for anything you do in your life. Instead of trying to bring him down maybe you should work at bringing yourself up.