Another former homeless person here.
If you had run across me in early winter of 1984, and it had crossed your mind to offer me money, would it have helped me? Let’s see…
a) Giving me $5 or less would’ve given me a meal. I would generally get one sooner or later anyway, including the free ones available at the city shelter, but the opportunity to get a better-quality meal would have been appreciated. Would it have crossed my mind to spend it on beer instead, insofar as I could get food (but not beer) for free from the city shelter later on? Yeah. I might’ve done that. I would’ve appreciated it either way. Your $5 donation would not, however, under conceivable circumstances, have changed my circumstances, and you’d be foolish to expect otherwise.
b) As a homeless person, I had really dismal connection to resources even when I had the money. Information plus money was always considerably more valuable than money alone. Free services were of enormous value. Might you have been able to offer me a place to do my laundry? A place to store some items so that, in order to own them at all, I did not necessarily have to lug them around everywhere I went? Would you be willing to take messages for me if I pretend your phone number is my own? Wow!)
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These things would not necessarily change my circumstances either, in and of themselves, but they might tip the balance. Now that’s assuming that I’m me – lucid (if somewhat discombobulated a bit by the experience), educated (HS only, no college, but literate and informally cognizant of a lot more than HS level education would suggest), healthy, English-speaking, and generally blessed with the cultural advantages of growing up middle class in America even if I lacked most of the material ones at the moment. Even for me, being a person with a spotty work history (none of it recent) and no college and no contacts to speak of made it hard to land and keep a job.
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c) So if you really wanted to make a difference, you could hire me. And cut me some slack initially, allowing for such things as the fact that I might be really hungry (perhaps you could pay me some right away, or take me out to breakfast the first day or something?) and still don’t have a home and probably won’t for some time (1st month, last month, half a month security, two references???). But an ongoing job, yeah, that would eventually make an enormous amount of difference.
d) It doesn’t have to be money, and it doesn’t have to be extending yourself in a way that involves ongoing risk to you. (Believe me, I do understand why you’re reluctant!) Buy me one of those phone cards that let me make calls. Go into the laundromat and make a deal with the owner, have the owner make out a homemade “coupon book” for doing laundry that you pay in advance for. Or perhaps you would buy me a PO Box and give me the key, my own address at which to receive mail? Incredible, you just made it plausible for me to submit a resume! Got an unused AOL “screen name” or the right to create an additional username&password with your ISP? I could use the library’s computer!
e) Being conversational with me as one city-dweller to another, and perhaps discussing politics, illiteracy in our public schools, or why you like one architectural style more than another…you have no idea how nice it is to have a real live conversation with a non-condescending person! Of course I will hope it will be an ongoing friendship, but I’ll understand and appreciate it anyway even if it’s just of the moment.