One of the most uncomfortable aspects of breastfeeding for me was that moment when the lactation consultant sidled up next to me and asked to watch my baby latch on. She helped with my posture, and pushed my nipple further into baby's mouth. In my case, she recommended a side lying position, since I have a disability and have difficulty using my arms to hold my baby.
Despite that hurdle, breastfeeding my two children has never been a struggle for me. They both were able to latch comfortably, and I was blessed to have enough milk. Am I just lucky? I recently discovered, that because of my disability, I was forced to engage in "laid-back breastfeeding," also known as "biological nurturing." It played no small part in my success, and I'm shocked that no one is talking about it.
Much like it sounds, laid-back breastfeeding allows mom and baby to relax and let nature lead the way. Mom kicks back and lets the baby essentially drape across her to reach the breast. When a nursling gets to lay face-down on the breast, gravity becomes your friend instead of something you have to fight. Suddenly, all the thrashing and kicking and pulling that you have to fend off while sitting up becomes helpful movement which enables your baby to position himself or the best latch possible. When you cradle a nursing baby in your arms, you and the baby are both fighting against gravity. It's tiring and it could be the source of any shallow latch problems you might be experiencing.
Of course, one of the more difficult things about this approach is that it really can't be accomplished in many places. If you are at home with your children all day long, then it's totally doable. But if you're out and about with your baby, you may have difficulty finding any place to nurse where you can physically lay back. Even so, if you and your baby are having difficulty, you might try just laying your little one (even if he's only an infant) on top of you and seeing what happens.
Sometimes, the more stressed out we are, the more we try to force things to happen the way we feel that they should. Breastfeeding is not one of those things that can easily be forced. And sometimes it can't be forced at all. However, you may find that your baby's instincts and your body can be trusted to work in unison more often than not.