Breastfeeding struggles

Since day 1 I’ve had to pump and use a nipple shield to feed my boy. He is 3 weeks old and yesterday I decided to remove the nipple shield and he finally latched and was able to properly breastfeed on both breasts a few times. I tried today and he’s not getting a good latch and it’s super painful.

I’ve looked up videos and tried my best to get him to latch properly. I also have my appt with the LC next week. It was so nice that he was properly bf yesterday and it’s boosted my supply. I’m bummed today.

Are there any tips and tricks from seasoned professionals?