Wanting to work

I have an 8month old who is exclusively breastfed since day one. He never really liked any of the nipples we tried so now he doesn't really know how to eat from one. Anyway I'm thinking I want to start working so we wont have to keep living paycheck to paycheck😑 I'm not sure if he would be ok with pumped milk in a sippy cup and just eat some solids or if he will want the boob since he is a comfort eater.

What did you mamas do or did you wait till they're done nursing so much throughout the day?