This quiz is all about the art of overcalling. The contested auction is a dark and mysterious (not to say dangerous) place. It is a necessary part of the game to try to push the opponents about, to try to win the auction if you can or, perhaps, to push the opponents beyond their comfort zone.
Just remember, though, that you can get badly burnt if you pick the wrong moment to bid. If the opponents have your suit well covered (we call it "having a trump stack") they will be quick to Double you for a large penalty. It is an under appreciated fact that the biggest penalties in bridge come from low level contracts after a poor overcall has been Doubled.
So you need to combine safety with aggression. Your parachute is the quality of your suit - in general try not to overcall with a poor suit...