To obey or not to obey??

If you are a mom, and your kid is old enough to express themselves, then I'm betting you've had a day or two (or all of them) when you think..."My kid doesn't listen to anything I say, am I doing ANYTHING right?" If you are a mom and you have never thought this, I am no longer your friend....hahaha. Well I feel like this a lot lately. Jerrick is starting to be much more independent and making his own choices. While Sammy is just at that age of discovering planet earth. I have to keep an eye on him and trust that Jerrick is behaving himself. Usually this doesn't go too well.
One of our rules is to not play with the DS or watch TV when Jerrick wakes up. This rule keeps him asleep until a decent time. I found him playing it at 5am before!!! So as Jerrick went to bed I noticed the DS was on his nightstand. I came in and talked to him and reinforced the rule. He looked at it and at me and said, " I think that maybe we should put it somewhere else that I can't see it in the morning." I was so proud!! He was choosing to make it easier for him to obey....he WANTED to obey, when sometimes I think he just tries to avoid being caught. This makes me very happy, thank you Jesus!
Let me just say that this more than one kid thing is rough. I feel that it's more complex in some ways since there is such a difference in age between my boys. The expectations and responsibilities for Jerrick are a LOT higher since he is 5 years older. I don't want him to be bitter toward his brother, but he is starting to get this... I think...The problem is that Sammy doesn't get it and wants to do everything big brother does. Teaching him to stay beside me in a parking lot is just at the start of my list. The question is, do I make Jerrick hold my hand (he is starting not to like this), so Sammy will? Do I trust Jerrick to hold Sammy's hand since I usually have a load of bags anyways? Do I keep a death hold grip on Sammy while he jerks and falls down and then laughs when I pull him up and makes it harder to walk? There has go to be an easier way to walk across a parking lot!!! For the most part I just try and hold him, but that kid is big!! I don't remember what I did with Jerrick, but I don't remember it being complicated??!!