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Don't have to worry about your friend's motives if you honestly want to help them.
Travel a little bit. Spend most of your time at home, either enjoying the simple pleasures, or with friends and family.
So what if they are taking advantage of you? You are rich! What's the downside?
Sure, you have to be vigilant against con artists, grifters, and addicts. You have to draw a line somewhere. Maybe don't fund their casino trips, drug trips, or Candy Crush high score.
Extravagant birthday gifts? College tuition for your niblings? Why not?
If someone is lying to you, you will find out eventually. I'd rather have friends now and let future me deal with the fallout from the grifters.
One of those guides to “what to do if you win the lottery” says to, up front, decide how much and who you want to fund. Want to buy all your friends and family houses and college tuition? Sure.
But the thing is that money can make people go crazy. Some people will always want more. Sure you got them a house, but you’re rich, why can’t you get them a car too? And now they’re a little behind on bills, surely you can help them out, right? And it never stops. Not everyone, but someone.
You might be interested in this podcast episode that touches on the subject: https://hiddenbrain.org/podcast/between-two-worlds/
That's tragic when it happens. I know that it will happen. Free lunches attract flies.
That doesn't mean you can't help people. It means you cut them off when it's clear they are being hurt and not helped.
The "why not" is that some people actually are harmed not helped by being handed stuff. I tried to help one of my friends who lived with me rent free for a year and by the end he was completely unmotivated to actually get or keep a job, contribute around the house, or even behave pleasantly towards anyone in the house. It happened gradually over time til living with him became intolerable.
Then you have a hard conversation.
I've been that person. I lived with my grandparents for a year. Rent free, nearly no job. My aunt and uncle sat me down and explained that they appreciated my work helping to care for my grandparents, but if I stayed with them I would only be qualified for a career as a home health aid.
I talked to my extended family and moved out. Other arrangements were made for my grandparents. I found a job and started a new career. It's certainly possible to enable bad behavior, but it's also possible to help someone that needs it.
Good on you for being receptive to their conversation and actually making improvements and changes. Not everyone behaves that way, some people like my friend just become dependent on the help instead. It's important to recognize that external help isn't always the solution; that shouldn't stop us from trying to help initially but it's important to withdraw it if it's causing dependency.
That's completely reasonable.