Pumping...maybe I am overthinking this

mcdmaw

For some reason, starting pumping was much easier with DD!  With DS I just can't figure out when is the best time to pump and when in his feeding time to do it??  I need to build up a freezer stash for my return to work (end of June) and also get a couple of bottles ready for some road trips (3-4 hours) this weekend.

He is generally just eating at one side but occasionally he will be hungry enough for two so I am hesitant to pump one side while I nurse.  Sometimes he goes 1.5 hours between feedings (from the start of the feeding) and sometimes he goes 2.5...so I don't always feel comfortable pumping after he has nursed.

 Any advice?  Am I just over thinking this?