What is the greatest challenge when you are total breastfeed and need to go out with your baby ?

I'd imagine just finding a place to breastfeed in peace and privacy would be hard if you go somewhere new and a place you're not necessary familiar with. I know some moms who can't seem to breastfeed because they are too self conscious in public, even in nursing rooms -- they call it performance anxiety of sorts. So they either go out for short periods of time, at nearby places and head home to feed baby or don't take baby with them if they need to be out and about for too long.