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Before going back to work and leaving your baby at the sitter's or at daycare for the first time, you may want to introduce them to the bottle first, just so that transferring to the bottle will not be an additional shock to their sense of security. It shouldn't take too much time to pump and feed with the bottle once a day so that it is not completely new to your baby, and nurse the rest of the day. This will also help you and your breasts get used to the pump quicker too.