Biggest mistake I did with my older baby was that I measured myself when I first started pumping and never measured them again, throught the pumping journey I would get sore and sometimes blistering nipples, so now with my son- I am 3 months in about to be 4 and I measured myself again and had to change to a smaller flange.
So just make sure you are using the proper flange for best comfort 
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I didn’t realize they could change! This is good to know, thank you for sharing.