A friend is "working on" rolling over with her DS. He's not in physical therapy or anything like that; she just turns his hips and encourages him to roll. My dad asked me what I want DS's first word to be and my neighbor seems to think I should teach DS to hold his own bottle. Now call me a bad Mama, but I had no intention of having mini-lessons with DS in any of these areas. (Granted, he is not behind. I understand if a LO has needs, then their parents should absolutely follow a therapist's program). I was just going to give DS lots of floor time, read and talk to him all day and let him grab the bottle from DH if/when he's ready (he's already trying). Am I wrong, here? Are we supposed to be having milestone tutoring with LO? Or, do we just let nature take its course?

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Re: Do you "work on" milestones?
This.
I don't work on milestones. I figure he will do them when he is ready. I repeat things to him all the time - like mama, papa, all the animal names when they come by.
My brother and his ex-wife used to repeat certain words to my niece all the time. They wanted her first word to be either mama or dada. Her first words were "a bite." LOL Every time we ate she would scream out "a bite" and open her mouth.
As long as your LO is developing on his own, I wouldn't do anything different
Jack does things when he's good and ready. Sometimes I'll work with him to strengthen his muscles (ie, hold his hands while he's on his back and help him pull himself up to sitting) but it's for a very few minutes every day, and not intended to actually help with the milestone itself, but to build the muscles to make that milestone possible.
I figure he and Nature know what is best and I'm not pushing him to do things any faster than he should by his own doing.
I do, especially now because LO is actually a little behind (still hasn't rolled or even attempted to roll at 7 months). So I try to get him to roll by turning his hips and clapping and getting excited.
He hates tummy time, so I do everything I can to encourage him to do it.
I also say syllables to him like "ma ma ma, ba ba ba, da da da"
By the way, if you do tummy time - isn't that 'working' on a milestone?