Ok, well not Uncling, but my brother-in-law is 11 so the experience is similar to being an uncle, and that's more succinct than brother-in-law-ing. Anyway...
Today, wife and I decided to take her 11 year old brother ice skating, but I proposed an experiment: offer him a chance to earn it, with a choice. We gently proposed to him that to go, we'd like him to do the dishes, but if he wanted, he could opt-out of the dishes and pay his own entry with his Christmas money.
I didn't know how much he had, but I wagered it was more than the $7 to get in, and that for a kid who got plenty of video games for Christmas, he might be willing to spend the $7 on something fun.
He was a bit taken aback at first, that I would ask him to pay for an activity that we were doing together. I'm not surprised at this as kids rarely, in my observation, pay for "experiences," but rather only for "things." After thinking for a minute, he said he'd rather pay than do the dishes.
As per the deal we agreed upon, when we went skating, he paid his entry and I paid ours. He even went so far as to suggest "I have money left over, so I'm going to buy myself some onion rings." Of course, I wouldn't have suggested he buy his own food, but he seemed to enjoy that he didn't have to ask, because it was his money, he could be the sole decision maker.
I'm not around him enough to know what he would normally spend money on, so we asked him, after, "so was this a good use of your money? Coming and doing something fun with us?" And he gladly said "yeah, and I still have money left over."
Wife and I agreed that the night was a success, and we went home happy. Unfortunately, that changed soon. Her mom confronted her with, "he had to pay his own way? Why?" And her dad with "we'll give him the money back." She felt a bit awkward, and didn't really respond, so the night ended with them unsure about why he "had to" pay. Again, I'm not with him often enough to know what he'd usually use his own money for, but I'm unsure of what would be more valuable than a fun time with his sister, if his parents don't think that's a good use of it.
The experiment was a genuine attempt to help him think about where money goes, how much it costs to do fun things, and the value of the money he has. I hope it got through and that the lesson doesn't become "mom and dad will pay me back later," because that won't always be the case - I know his family enough to know that.
Alas, I suppose I will be able to try again with my own kids one day. For now, I'm a little disappointed. Thoughts?