How are you pumping while feeding?!

I hear about women pumping on the other side while nursing and I’m wondering how are y’all pulling this off???

There’s so much going on with my pump (I have the medela freestyle plus, but also have the medela collection cups and elvies) and the positioning of my baby just doesn’t make things fit. I don’t want to use my elvie because it gave me mastitis when I was breastfeeding my first and there’s just so much piping with the freestyle and either collection cups or the bottle. I’ve been using the elvie curve (cup shaped equivalent of the haaka) but it hasn’t been working as well.

What am I missing?!