The point I'm trying to say really is in order to mirror talent, certain players should earn skill points easier or harder. So if I start a career player generally I would have to play one shot really well 10times before my skill goes up a level in that shot (making it easier to play well)... But occasionally you would get a career player who levelled up after 5 shots, or 15 etc.
(Or however the skill mechanic works in the game, the above is just an illustration)
So you can always succeed or fail, but it adds variation to each iteration of the career, and acknowledges that not everyone can be Tendulkar, and some poor bastard has to be Kerrigan