Oh yeah, my progression towards the end goal of DD falling asleep was loooong. I started first by talking about her falling asleep on her own, usually during the day, using a cheerful and enthusiastic voice. I said that since she was now 2, we would have 2 stories and 2 songs, 2 kisses goodnight and 2 I-Love-Yous and then she could fall asleep.
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After that, I started with the routine, telling her that I'd be in the adjoining bathroom brushing my teeth, washing my face and other things. She didn't like the idea at all, so I did a practice run during the day. The first few nights of our new routine, I had to stand outside the bedroom door and catch her as she tried to bolt out of the room. She wasn't happy with being alone in there, and there were tears. I never let her cry though. I would simply put her back to bed saying "I love you, goodnight", and give her a hug and a kiss. After the first few attempts at bolting, I told her mama wasn't happy and simply put her back to bed with a hug and a kiss. Eventually, I put her bad to bed without a word. It took a good two weeks of doing this for her to feel confident about staying in the bedroom alone (and this is WITH a nightlight and her Twilight Turtle)...and I won't lie: it was tough. I would text my friend who would "hold my hand" through the process, reminding me that I wasn't letting her CIO, but just teaching her a new routine.
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When she was comfortable in bed alone, but still awake, I would go about my nighttime bathroom routine, making lots of noise so she knew I was there. I'd check in every once in a while to make sure she was ok. Eventually, as in a few weeks later, we transitioned to me going to read in an adjoining bedroom, so she could come to me if she was scared but would still have to be alone in the bedroom (door open, nightlights on). Now at 3 years old, she is comfortable with the routine and will sometimes ask me to stay with her. I usually tell her I'll stay 5 minutes but only if she keeps her eyes closed and tries to sleep. There have been a few nights where she wasn't asleep when I left, but she was drowsy and comfortable with her teddy bear and blankie. Other nights, she's out like a light within 5 minutes. It comes and goes as her insecurities come and go.
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Good luck!