I have a 4m old and I work 11p-7a. I feed and put him to bed by 8, pump around 10 before work. Try to pump once at work (usually between 2-4) but I work in a busy birthing center and I am lucky to pee during my shift so some shifts I don't pump. I pump right when I get home around 8am, I will nurse around 9 and then sleep few hours and then pump when I wake up from my nap. I have a decent supply, I've never supplemented and I keep up with his needs but I don't have a huge freezer stash or anything. You can do it, it takes a lot of extra work but it's worth it!