When Should I Stop?

"It is not what you do for your children, but what you have taught them to do for themselves that will make them successful human beings." - Ann Landers


I have a question for all those moms out there, particularly those who have older or grown children:  When should I stop?  As in, when should I stop putting toothpaste on their toothbrushes to make sure they ACTUALLY brush their teeth?  When should I stop making EVERY. SINGLE. meal and pouring EVERY. SINGLE. drink for them?  When should I scale back on the one-on-one attention when it comes to all schoolwork?  When should I stop doing their dishes and laundry and expect THEM to start doing things for ME for a change?  When (if ever) will I stop feeling so incredibly overwhelmed?

I don't remember a single morning in my childhood when my mother got up and made us breakfast.  She certainly never reminded me to brush my teeth.  I can probably count on one hand how many times she made me lunch to take to school.  (Which is how I ended up with a horrible sugar addition, packing myself nothing but King Dons and Ho Ho's all those years!)  What I remember of those hectic school mornings was the four of us getting up and ready all on our own and she coming down the stairs just a few minutes before we left for the bus stop to watch us out the window as we ran down the street.  And if we ever missed the bus???  Let's not even talk about when THAT happened!
Having to actually DRIVE us the five miles to school?  Oh, the HORROR!

William will be 5 in a couple of weeks and Luke is only 3, so I get that they have a few years yet before they start stepping up.  But Sammy is almost 8 and Owen will be 10 in July - isn't it high-time they start fending for themselves a little bit?  What's a mom to do, when I know that without me to remind them to brush their teeth they will literally NEVER do it?  I don't think they'll starve without me to prepare their meals, but do I really want them eating nothing but Animal Crackers all day?  And school....don't get me started on the school!  It's 5:30pm as I type this and Owen is on his 4th hour of working on his writing assignment.  He had to make 30 index cards, each with one fact about speedskating, and it took him over 2 hours.  I feel like I can't get ANYTHING else done these days and it's affecting my psyche.

So, please weigh in here.  Should I expect more of them?  If so, how do I get started?