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Originally Posted by VisionaryMom 
So, there are 2 issues. The first is that I don't want him (or DD, for that matter) to feel entitled, and maybe that's a better word than grateful. They're white (blond hair, blue eyes, & all) and upper middle-class. They live in a stable house with 2 parents, meals cooked from scratch, have a dog. They are the American Dream come to life. (And no, I don't say that to them. This is my adult interpretation.) DS was sick when he was younger, and we moved mountains to get the right specialists and spend untold money on his medical care. My children are INCREDIBLY FORTUNATE, and I don't want that to turn into a feeling that they deserve everything. DH & I aren't materialistic, and we try very hard to be conscious consumers. At the same time, one of our children wants more and better of everything, and it does concern me.
A few years ago, someone we know was turning 16. Her parents bought her a car, and she complained because it was 3 years old and not the color she would have picked. It was a gift! Her parents stretched to buy that car! That's what I want to work on with DS. I don't think it's entirely personality, and I'm looking for concrete ways to help/teach him.
The second issue is that I imagine it's miserable. If we read 2 books to DS, he wants 3. If we read 3, he wants 4. The problem is that he spends so much time thinking about getting us to read one.more book that he can't enjoy reading the first ones. I want him to learn to slow down and enjoy what he has in front of him because otherwise, I don't see him enjoying things as much as he could. I struggle with being present in the moment, too, so it's not an assault on DS' personality. It's just something I see as a parent that I believe I can help him work to make his quality of life better.
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Wow there's a lot here. I just want to say up front that I agree with your goals and I think it is something to address.
However I also think at 5 your tools are limited.
For a global sense of entitlement, I personally believe the best way to help our kids is to expose them to ways to truly experience things. So as your kids get older I would look for ways to engage them with poverty (volunteering, travelling); help them learn to work for money, save and budget and spend, and don't provide everything their little hearts desire, particularly as they get closer to adulthood.
But at 5, a lot of that isn't super practical or appropriate, so I think to worry about the car-at-16 scenario is premature. He just won't have that cognitive perspective about others and the world for years. I would deal with what's an issue today, and leave the rest for a while.
Your son also sounds like he may have gone through a lot that has added to his personality for pessimism. Medical trauma can really have that effect on him - it's a nice myth that sick kids all get holy, but a lot of them internalize that there may be another IV around the corner sticking them in the arm. So I think in some ways I would give him some added time to develop a more optimistic view.
For the books and gifts and things, I think that you can address it to a point - and after that he's going to have the emotions he's going to have. I'd just treat it very, very matter-of-factly. "That's what Grandma could spend, and otherwise you wouldn't have anything to spend. Let's enjoy this."
In other words I'd try to give him the consistent message that he CAN and WILL get past these negative feelings - they are ok, but move on. (And behave appropriately.)
With the books, if that's a good place to focus on being present, ALWAYS with 100% consistency agree on the number in advance. Tell him directly that there will be no more, but that you would like him to try to enjoy the ones you are reading. Maybe do a few yoga breaths to focus. And then enjoy them! If he doesn't, he doesn't. He will someday, particularly if there is infectious enthusiasm around him. As he gets older
My son is optimistic in many ways but he's also a 'planner' - he is the kind of kid who is thinking about the next book, sometimes. This is a really positive personality trait in a lot of situations. Just not so much when trying to get more.
