Referring to the deep end of the swimming pool. Most people learning to swim will start where they can touch the bottom and keep their head above water. Others will jump in at the deep end and sink or swim! If you want to learn to be a food server, starting on the busiest night of the week is jumping in at the deep end. If you want to learn to raise rabbits and start off with a hundred of them, that is jumping in at the deep end. One would hope you had received instruction before doing any of these things. So, while it does imply some courage and risk taking, it does not have to mean you are irrational.