A- is becoming more opinionated, which is a good thing. I can be more opinionated, too. We can start talking about reasons, and we can work on weathering big emotions. I've been erring on the side of permissiveness and allowing self-determination, but maybe I can trust in her resilience and adaptability. Here are some areas I might work on being more firm about:

Weaning: A- asks to nurse for comfort and to help her go back to sleep. Sometimes she stays latched for a long time. The dental surgeon strongly recommended weaning her to reduce the risk of further cavities and repeat dental surgery. I know there are mixed results regarding night nursing and early childhood caries. Still, it's probably as good a time as any to make the transition.

I've been slowly getting A- used to waiting or finding other ways to comfort herself during the day. Sometimes she gets upset for five to ten minutes, but that's bearable. It's a bit more challenging at night. I won't push it too much at night because we have a long trip coming up. When we get back, it might be good to try something like Dr. Gordon's method.

What could being too soft look like? If I give in to her, she'll probably stick with nursing on demand for a year or more. We'd probably need to go for another round of dental surgery with its associated risks, costs, and finger-wagging. It's easier for me in the short term to night nurse instead of wean, but I might be missing out on long-term sleep improvements.

What could being too hard look like? If I push her too fast, she'll cry a lot and we won't get much sleep. Lots of people have survived cry-it-out methods, but I'm still hoping to do something a bit gentler. I feel better about her crying if I'm there offering a hug or a backrub. She's usually so upset that she doesn't want me to touch her, which I respect, so I just hang out and listen until she settles down. The first time we tried it, she cried for an hour before falling asleep. She seems much better at recovering now.

• Eating: A- likes playing while we have dinner, and sometimes wants to pull me away. I like sitting down for dinner with W-. I'm getting better at insisting that I will come play with her after I finish my dinner. We keep her dinner on the table until we're done, since she often wants to sit down for dinner when she realizes we're enjoying ours.

She tends to eat food every 1.5-2 hours. It might be good to stretch it out a little further.

We plan to move a little away from snacking on the go when we're out and about. It's better to sit down and have proper snacks, anyway.

• Sleep: I can be more firm about waking her up from her afternoon nap so that we don't end up staying up too late in the evening. I'm also thinking of being more firm about my own bedtime, although she's welcome to stay up and play a little if she wants.

I think the general plan is to trust in A-‘s resilience and adaptability, and to not be afraid of the hard stuff. We'll figure this out together. She wants to learn how to be a big kid, and I want to help her. I don't want things to feel like a power struggle if I can help it. I want it to be more like “Okay, you're ready for bigger challenges. Let's try this together.”

As for brushing teeth, we'll try working on playfulness first. Lots of parents take a firmer approach, but the dentist doesn't recommend restraining A- for toothbrushing, so we'll just have to work on making it more fun.