I'm embarrassed to admit this, but my son started falling asleep on his own just three months ago. Before that, he needed my husband or me to lie down with him until he fell asleep. We tried all kinds of incentives and punishments, but things didn't get better for us until a couple of months before his third birthday. When I'd hear other mothers talk about how easily their kids fell asleep on their own, I'd wonder where we went wrong.
Thankfully, Kellan falls asleep without much of a fuss on most nights. But on the nights when he does put up a fight, it's a full- scale battle. The first stage is all about politeness. "May I have a bowl of Cheerios and milk? Please Mama?" When we refuse to give in, he moves on to desperation stage, where requests to read one more book or have one tiny bowl of cereal is amped up and repeated over and over again, sometimes to the rhythm of pounding feet on the wall. Finally comes the hysterical phase, and I hope the neighbors don't hear him wailing through an open window.
It seems like there's always something - illness, new anxieties, changes in routine - that sets us back to square one in our bedtime battles. We've noticed Kellan talks about monsters and feels separation anxiety at night. We're doing our best to reassure him and I am trying extra, extra, extra hard (notice all the extras?) not to get exasperated when he wants to cling to me like a peach to its pit.
I've been reading up on increasing our chances for a peaceful bedtime routine. One thing that's worked for us is to let him pick his three bedtime books and remind him that the lights go out after we've read them. He also loves when we tell stories, so we sometimes negotiate a make-believe story in the routine as well. If we hear him playing with a toy in bed, we just let it go. As long as he's happy to wind down on his own, I have no problem letting him talk himself to sleep. I check in on him to make sure he's not sleeping on top of something.
I remember not being a great sleeper when I was a kid and now I have a whole new appreciation for my parents.