I think it's best to start a few weeks before school begins. This lets the family enjoy the remaining weeks of the summer, while preparing for the new school year. For example, with our young son, I remind him about 3 weeks before school starts that we will soon be practicing our school schedule with no more late nights, like when we stayed up to watch fireworks on the 4th of July. (It helps our little guy to give specific examples). I will let him choose a "final" weekend night where we go down the street for ice cream and stay up a bit later, or watch a movie-- something that is special to him. Then, two weeks before school we start his usual bedtime routine, ensuring he gets about 10 and a half hours of sleep before we wake him around 7 a.m.. This is his normal wake up time for school. We will do this gradually; if he's been waking up closer to 8 a.m. we will wake him at 7:45 for a few days, then 7:30 for a few days, etc. Of course, with an older child they may be setting an alarm and doing this more independently. Our bedtime routine NEVER waivers. For example, we read and snuggle in bed every night, though we may alter how long we read if it's been one of those rare late nights. I find the same bedtime routine is crucial to having fewer bedtime problems. Additionally, if for some reason our little boy has become upset during bedtime, we make sure to regroup and end on a loving, peaceful note, no matter what. If that means the parents have to take a brief time-out, so be it!
Yes, the child should be transitioning to the school schedule two weeks before school starts as opposed to making that transition in the first weeks of school. You want your child to be well rested and content while he or she is getting acquainted with new teachers, new schoolmates and any new school routines. With that said, our family does not veer from our routines radically over the summer in the first place. I think that sleep is so important to a child's mood and health, regardless of their age. As a result we don't have many "late nights" even during the summer. When we do have a later night, we will label it as such and encourage our little guy to sleep in the next morning. For example, with our little boy Lorenzo, we were recently on vacation and let him stay up to swim in the pool past his usual bedtime, but clearly noted that that was a special summertime treat. Since we were on vacation, he was able to sleep in a bit the next day. The next night, even though it was vacation time, we put him to bed at his usual time to catch up on his sleep, and to help him feel his best the next day. Make sure you know from books or your pediatrician how much sleep your child needs at any given age.
Again, I'm not a big fan of changing sleep habits much, even during summertime. I know families who let their children stay up till they fall asleep from exhaustion, but I think children do better with more structure.
By not changing things too much over the summer, it's easier to stay on a healthy track. Nonetheless, I think it's fun to be a bit more lenient during summertime. In our family, we rarely eat junk food or candy (easiest if those things aren't in the house at all, of course!). On the other hand, Lorenzo was in a circus camp for a couple of weeks, and the last day of each week we let him have something from the vending machine at the camp. He had seen some children who were allowed to bring money for the vending machine each day. We explained to him that it's not healthy to eat that sort of food daily, but we'd give him a dollar for Friday to buy something that he chose from the vending machine. He was very happy about that, and it helped him to not feel so different from his peers. However, during the school year and even most days of summer we are so used to saying "No, that's not healthy enough" to any similar requests that our son is less apt to ask for unhealthy food in the first place. (But don't get me wrong; we often have to set limits and can sound like any other parents. I think that's part of the job description!).
You keep saying "No". If your child or teen says "Why?" you explain your reasons (in our case, "Because it's not good for your body to have candy very often" or, "Remember, we said we'd only go to the ice cream parlor once a month, and we just went last week. Would you like to go the first Saturday in July, with one of your friends?"). With a teen this may be harder, of course, depending on how independent they are. By that age, we hope our children have internalized some of these healthy habits, and make better choices on their own!
I wouldn't worry about trying to have a more classroom like frame of mind before school starts. They will have so much classroom time and structure then! But we might remind our son that once school starts he'll "get" to have homework again, and will be able to practice his writing, and will be reading to us more often. We've always stressed that school is exciting, not a chore, and a new adventure where he gets to be in a new grade and reconnect with teachers and school friends.
Above all else, stay calm. You are the adult. The most important thing in life is love, and let your child know daily they are loved while working on your own patience. The book "Time Out For Parents" by Cheri Huber is a lovely, simple-to-read book that emphasizes this philosophy. On a practical level, make sure you have plenty of time to get yourself ready on a school morning before you focus on helping your child get ready. If I've lost my sense of calm during the morning routine I always regroup by saying "Let's be present" with Lorenzo. We both know what that means: to look at each other, take a breath and just be calm and…present. Taking that 30 seconds will not make you late, and it will reestablish your connection with your child. Being on time is important, and you want to teach your child that, but being connected and peaceful during the process is even more important. Similarly, if anything has gotten so off track that your child is crying, take the time to comfort and calm your little one. Try to always leave the house calm and happy.
Always, always empathize. I'm not a fan of saying "You're o.k." when your child is not feeling o.k.. It's crucial to help them know it's all right to be anxious, sad, or any other so-called negative emotion. Among other things, that will help them become strong and emotionally intelligent. You might bring in your own childhood experiences to help with that, such as, "I remember I was so nervous to go to high school; it seemed so enormous!" Only after empathizing and really helping your child to feel understood would you problem-solve. Using the example that you just gave, if you're child is worried about someone being mean to them, you might try brainstorming with them about different ways they might handle that situation. Remember to remind them them that there are adults to help if need be. With a younger child who is feeling anxious, you might also teach them self-soothing techniques (breathing, humming a special song, cuddling with a lovey). If you've taken the time to do this, by the time your child is a teen they will be skilled at that (hopefully!).
I think that covers most of it, but I can't stress enough how important it is to remember how precious our children are, and to let them know that daily. It can be so challenging being a parent, and that's another article altogether, but if we always come back to our love and their basic innocence and sweet vulnerability, we will be doing our best for our little ones.