Replying to Progression

ok so i feel like im really behind cause my friend out in CO ive seen him in some vids and he is really sick (kid with ronin suit in keystone opening day video). this is making me feel really sucky and i guess this is kinda a dumb question but is the best way to progress to just like huck..i mean like if i wanna get better on rails dont be afraid to do a bunch of sit just go for a 270/450 etc disaster and deal with the consequences or go for a cork 7. i dont think anyone will understand this but if you do tell me how you guys make your major progression