Before I even had children, even before I was pregnant, I knew that breastfeeding was something I wanted to try. When my son was born, there was a bit of a learning curve, but I fortunately caught on pretty quickly (within a few weeks), and that was that. My goal from the outset was to continue breastfeeding for one year, and it felt like that mark came and went pretty quickly. So now the question was no longer “how long will I continue?” it was “how long until I stop?”
I should take this moment to point out something kind of important: I’m speaking only for myself here. And who am I? I am someone who was fortunate enough to have breastfeeding work out for me and reach the goal I had (kind of, sort of) set for myself. I can’t pretend to know the emotional process of someone who decides to stop breastfeeding for any other reason than her and/or her kid's own readiness. Some women decide to stop because nursing makes her completely miserable, or her baby isn’t gaining enough weight, or her pumping schedule at work is too demanding, or her child self-weans, or she just doesn't want to do it, and those are all unquestionably valid reasons to stop.
Given how challenging (or downright impossible, or inadvisable) it is so for many women to breastfeed, "when do I stop?" wasn't a question I had foreseen needing to answer, but there I was.
Continuing the first couple months after the one year mark was a no brainer: He wasn’t interested in weaning and I wasn’t interested in weaning him. Breastfeeding was routine. It was so easy at that point, and there were benefits above and beyond all the health and emotional ones you’re always hearing about. For example, if I wanted him to stop crying? Boob. If I wanted him to go to sleep? Boob. (I swear, breastmilk is a sleeping potion.) If I wanted him to remain calm on a cross country plane trip? Boob. So it really came down to: “Why would I give up this amazing tool in my mom arsenal?” The answer would come over the course of the next few months, when breastfeeding wound up becoming waaaay more annoying than useful. Thus began the emotional journey of deciding to stop breastfeeding.