big (((((((((HUGS))))))))) to you!
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It's so hard when these lo's don't do what we want them to do...
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I went back to look at the notes I took when Jackson was this age.
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He would be able to only do 1hr 45 min (sometimes 2hrs) in the am then by afternoon he was way too tired to make it past 1hr 35min. We were trying to transition him to 4hr Easy and so there were a lot of days where half of his nap time I spent doing PU/PD!
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It was sooooo tiring!! Jackson was for sure still having 3 naps plus a catnap a day at Zanders age. By having a windown routine...it doesn't necessarily mean that you have to sit and snuggle with him. Just that you do the same thing every time so they know what is coming next. So for example, our windown routine when Jackson was younger and needed a longer windown was: brush his teeth, change his bum, put on a warm sweater, read a book, give him his lovey, turn out the lights and sing him itsy-bitsy spider, put him in his crib saying the same thing "have a good sleep, I love you, I'll come get you when you wake up". The whole windown was about 15-20 min long but after a couple weeks of consistently doing the same thing, he started falling asleep as soon as you sit in the chair with him. Now our winddown is changing his bum, sitting in the chair, giving him his lovey, turnigni out the lights and singing to him. It takes me about 5 min now to get him to his crib.
Do you think you may be going to him too soon once he wakes? I found that every now and again that if I left Jackson to talk to himself he would fall back to sleep. Maybe you are rushing in and he is waking because he knows you will be in shortly?
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Just a thought. I would leave Jackson in his crib until he started to complain then get him up.