Sweetest Boy.

Putting Jack to bed has recently proven tricky. He will usually throw a crying fit in his bed or wander out of his room...
My newest approach, though misleading, has worked lately. I will read stories, say prayers, tuck him in, turn on "snoopy" (the Charlie Brown Christmas Soundtrack he listens to every night..) and then say to him "Ok, I'll be right back!" and he says "Ok" and patiently waits my return.. falling asleep while doing so.

See, he wants me to sleep there next to him. Which not only to I NOT want to do because he needs to learn to get to sleep alone, but because it's very uncomfortable, and I like to use "Jack sleep" time as "Special Lisa" time.

So I'll tell him I will be back and I leave the door open so he can hear me around the house, then he eventually falls asleep waiting. I KNOW it's mean. BUT- he's learning that it is part of the ritual and he stays in bed and finds ways to get to sleep on his own.
FOR EXAMPLE. Tonight, as I type here and Jack is "waiting" for me in the next room, I hear him start to sing.
It is a lovely combination of "Old McDonald" and "The Wheels On the Bus" using the melody from "Wheels" and the characters from the farm, as follows:

The duck on the bus goes quack, quack, quack,
quack, quack, quack,
quack, quack, quack.
The duck on the bus goes quack, quack, quack,
All through the town.

The puppy on the bus goes arf, arf, arf,
arf, arf, arf
arf, arf, arf.
The puppy on the bus goes arf, arf, arf,
All through the town.

And so he sings himself to sleep.

Success.