Guys, just a little update, and a shoutout to Villanelle who suggested I think of the cause of her poverty in order to determine how to help her best.
I've been chatting with her and been thinking a lot about her situation and have come to the conclusion that the root of her problem is her mindset. Yes, there is the undeniable fact that she's got a rough life but everyone (eventually) learns life is unfair and we play the cards we're dealt with. However, she never gets past the self-pity party stage and therefore she could never pull herself by the bootstrap and people are avoiding her because she is such a bummer (conversations with her will always lead to her lack of money and poor living conditions, and if show sympathy, she will inevitably ask for handouts).
I think everyone just doesn't know how to tell her 'stop with the pity party, will ya? and start doing something!' because she may interpret that as mean as opposed to tough love.
I've been researching Christian counseling in her area (she told me she goes to church so I think she might be more open to Christian-based counseling). I plan to talk to her about going to counseling next time we meet. I will pay for it because then there is no way she would misuse the money as I will pay directly to the organization.
Just thought other people dealing with similar situation could use this as an idea.
Have you thought about how you will pose this solution to her? Offering counseling might come off a bit condescending (ie you think there is something "wrong" with her and needs to be fixed) so make sure you put some thought into how you approach this. It could backfire badly, are you prepared for that?
I would suggest bringing up in casual conversation what she thinks about counseling. Some people have a very negative view of it. But if she seems positive about it helping other people, then that is valuable information to have.
I would hesitate to suggest her going to counseling unless you had first-had experience with counseling and could say something like "you know, I went to a few counseling sessions and they were really helpful with addressing a problem I was having in my life. Have you ever thought about going to one? Perhaps they may have some alternative ideas to help with [problem she recently complained about]."
However, I really do think this will be awkward -- counseling really only works if the patient truly desires to make changes in their life and has the drive to seek that help to change. If she isn't really interested in it for whatever reason, she could easily get offended.
Instead, I suggest you gently "confront" her when she starts moaning about her circumstances. You say she never gets past the pity party stage to the problem solving stage -- you don't have to be mean about it, approach it as more of a curious, loving person who wants to know more about her and her circumstances, but firm in moving her out of self-pity and keep bringing the conversation back to problem solving and prompting her to brainstorm or generate ideas, and it is very important to validate both her capability and ability to solve this herself, her intelligence, etc in a genuine way. I do this all the time as a facilitator.
"blah blah blah my life is so hard because I'm poor! If I could just have $20..."
"what do you think would help your situation, Suzy?"
"huh? well, nothing. I'm just stuck in this poverty cycle forever. There's nothing I can do."
*upbeat* "I don't believe that for one second! I think you are a really smart person and there are so many opportunities out there. I'm sure we can solve this. Let's try to think of some ideas!"
"what's the point? Nothing will ever change."
*smiling* "not with that attitude! Here, we will both take a blank piece of paper. Lets see who can come up with the most crazy, outlandish solutions to your money problems in 3 minutes. Winning the lottery, starting a lemonade stand, counterfeiting, kidnapping someone rich for ransom..." ((you are priming her with this, and try to lead her towards ideas that generate continual income, not just one-off windfalls. I just put some random ones in there that I thought of first that are mostly windfalls because those are easy)) -- an added bonus, you could sneak in "financial counseling" or some such into your list and spark a conversation about it.
Now, take your lists and laugh at them. Talk about how fun/crazy/amazing those outlandish ones would be. Then notice a more realistic one and comment on it and see what her reaction is. Bring the conversation more toward realistic solutions. You'll see her start to engage a bit more, sitting up straighter, paying more attention -- people naturally begin to do this when a problem that is bothering them has a solution that is starting to take shape. But still keep the conversation light and no-pressure, you don't want to spook her. What you want with this first conversation is to expose her to this new problem-solving mindset. Look! There was a problem, and look at all the cool, fun, and also realistic ideas we came up with to actually solve it! Gauge her reaction to this, if she is getting overwhelmed or annoyed or tired, you can leave it there. But if she seems encouraging, you could push it a bit more and see if she is interested in pursuing one of the ideas. If yes, great! You can help her there. If not, then leave it alone and drift the conversation to something else.
Now, keep doing this. Redirect her EVERY TIME she starts going down the self-pity spiral and attempt to turn her mind towards problem-solving. Keep turning her back and back and back even if she tries to return to her comfort zone, but reiterate that you think she is smart and capable enough to solve this.
Meet every mopey "I'm poor and sad" with some variation of "Do you have any ideas on how to handle this?" "How would you like to handle that?" "What would make this better?" "What could you do to help the situation?" "what do you want to DO about it?" "Are there any solutions we haven't thought of?" "What else?" -- all encouraging, all cheerful, and also firm. Doing this redirection instantly shifts the conversation and mindset from passive to active, and she is more likely to follow through because SHE generated the ideas herself and has pride in that.