My plan was always to let my son self-wean. Even though he was still nursing like a newborn at two years old, I didn't want to force him off before he was ready. Many times I considered night weaning. I wondered if night nursing was keeping my son up at night, and wanted desperately to get a full night of sleep. Yet, any time I tried to deny him milk at night I realized that neither of us were ready. My son seemed incredibly distressed and I didn't have the heart to tell him no, nor the will to fight him in my sleep deprived state.
So, what changed? When I got pregnant with our second, I decided to try night weaning again. For me, it was incredibly important that he didn't view weaning as even remotely related to the new baby. I didn't want him to feel forced out and I wanted to give him plenty of time to learn to rely on me for comfort in other ways before potentially being forced to by a decreasing supply or newborn. So, this time I was more dedicated to it and I also felt like Henry was more ready.
At the beginning of my pregnancy, before he even knew about it, he had started telling me that my milky tasted "old" (how he describes food when it doesn't taste good to him). He's since stopped calling it old, but has dramatically reduced his daytime nursing. The first few nights weren't easy. So often I wanted to give in--both because I was tired and can't handle seeing him so distressed. However, I knew that, if I really wanted to give it a try, I must stand my ground. Giving in would just prolong the challenge for both of us. I would pat his back, hold him, offer him water, tell him I loved him, explain that milkies were sleeping, and sometimes get up out of bed with him. It wasn't easy, but it was way easier than I expected.
Within a few nights he was sleeping, accepting water, and falling back asleep without a fight or any tears. Now (please don't jinx it) he is sleeping through the night on most nights. When he does wake he usually doesn't even need me to help him back to sleep. He will drink his water on his own and then fall asleep holding his water bottle like a stuffed animal or security blanket. Every so often he will ask. Sometimes I'll even compromise and give him a waffle to help him back to sleep. But, I haven't given him milk before 4:30am in a while now (I usually try to keep him off until at least 5am, and he's been consistently making it until 5:30 or 6am recently).
For the first couple weeks I would give Henry a five minute and then one minute warning reminding him that milkies were about to "go night night until morning." Still every day when he wakes and asks for it I praise him on his sleep, telling him he can have milky now because it's morning and that I'm so proud of him. I also would brag about his sleep in front of him to my husband for the first few weeks.
Another thing we did while beginning night weaning was keep me in the room, but out of the bed. I slept on a twin mattress on the floor while my husband and son slept in the bed. I have since returned to the bed without issue.
Overall, I think the success is a combination of both of our readiness. I don't think night weaning would have worked earlier, and I realize there may still be bumps in the road. But, overall the transition was much smoother than I thought and I think both of us are feeling much more rested as a result.