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You're right about not giving a very large amount of money to people who aren't ready for it. When the protagonist of this article gave money to his daughter, he was basically giving her the same problem he had.

I'd feel obligated to pay for modest things for family and friends, like large holiday and birthday gifts, partial college for nieces and nephews -- maybe buy an "AirBnB condo" near campus and give them free room & board. Maybe give away a cheap good used car every year. Maybe angel invest in a couple of friends' startups.

Maybe it's because of my poor roots, but I would try to help out the people around me who've helped me in the past, in small ways.

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