breasting question/please help

Alejandra • Baby Boy Thiago was born September 23, 2016💙
So my LO is 3 weeks and has a pretty good schedule. Eats every two hours during the day and every four hours during the night. My question is how do you know when his full after each feeding and should I get up between those four hour naps to pump? I take fenugreek and mothers milk to increase my supply because I was very worried when it took him three weeks to regain birth weight. I'm currently wearing a nipple shield and I believe it messes with how much he sucks out. 
During the two night feedings my boobs are extremely engorgaged... once they where purple. I've cut back on the fenugreek pills since then.
Please don't judge my dumb questions. I'm a first time mom and the first in my moms side to breastfeed