In working with disadvantaged people who need your help, should one work towards a goal one has in mind for this person, or should one look at the motivation that that person has in asking for help, and support that motivation? Which is more important, their motivation or the one you’ve come up with?
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Another good question. I couldn't hope to give any kind of comprehensive answer but what comes to mind is the golden rule (do onto others as you would have them do onto you) and the "platinum rule" (do onto others as they would want to be treated).
I suppose a lot depends on your level of skill and qualification. If you are a qualified therapist or social worker then providing aid that you deem to be most helpful could be better. Or perhaps much depends on the exact motivation of the person asking for help, if they're in a bad financial situation and want you to help them rob a bank with them, then maybe a solution of your making would be better.
I also think of my relationship with my emotionally stunted, alcoholic father after I had been a Buddhist for a while. I stopped trying to fix him and would instead give him things that he liked, like cigars or mixed nuts.
I think, in the end, there isn't a right answer. We need to be wise, take the situation as it is and make a judgement call.
Thanks @Person ... Ive been discussing this with a few people of my acquaintance and that seems to be the conclusion, that there is no single rule here but you need to think it through on a case by case basis, keeping in mind a respectful and compassionate approach.
Sometimes people need an extra push, and then you can perhaps supply a goal or widen their view, but ultimately the motivation to do things needs to come from them because otherwise it won’t stick.
As with Buddhism -- just speak your piece and let the other fellow find out for him- or her-self.
On topic of paramita of generosity one gives what is desired by that being. However you shouldn't give things that harm them. For example don't give food and drink to gluttons. Also as they are disadvantaged I think they should be given things that protect them and steady their lives. Pure method of giving is with devotion, respect, by your own hand, in time, and without harming. In time means that when you have wealth that is the time to give. With devotion means that you are happy to give before, after, and during. Without harming means for example you don't give something that harms others of your relations. For example you give all of your time to something and have no time for friends family. Another example of harming wealth is giving wealth that was stolen or cheated.
The first two things you can give them might be the gift of what Thich Nhat Hahn describes as deep listening — without any sort of agenda.
And then being there for them as nuch as is possible as a kalyana mitta or spiritual friend at their need.
The answer to your query may come clearer with those in play (though your concern sounds like such efforts have already begun).
I certainly think that when one is stuck, it is often due to wrong perceptions. Pointing where a friend, or anyone who needs help, has clouded vision can often be enough to put them on the right track.
As @dhammika just said, listening is one of the most valuable gifts you can give another. Often, they will notice things about their own situation even just by speaking them out loud.