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Was having a debate with another Jewish friend of mine (I'm not Jewish, but an interested party) about something I recently did/have been known to do on occasion.

If a person I regularly do business with (Babysitter, Handyman, etc.) says they're falling on hard times, I've been known to give them a lift by pre-purchasing services from them ahead, they pay me back in service credits later.

I've argued before that this is at the highest level, since I'm offering a job, often up to what they need, but sometimes (including recently) I can't do that either with falling short, so usually what I'm comfy with.

My friend disagrees, says I need to make sure they're no longer needy at whatever cost...

Can someone settle this debate on where I stand Tzedakah wise?

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    Everything you do to help is Tzedakah. Sure it would be great if we could solve everyone's problems. But we can't. So do your best. that's IMHO. – David Kenner Oct 18 '18 at 3:51
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    while what you are doing has elements of the 8th level, it does not allow them to be off your particular dole in the long run. – rosends Oct 18 '18 at 10:28
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It sounds like you are mostly correct in this debate. Indeed, the best charity is enabling the poor person to become financially independent. The ideal would seem to be a business collaboration, rather than a handout, that generates future income for all parties. (See, e.g., Maimonides Laws of Charity, 10:7–14.) Such an approach provides for the poor person in the long term, and simultaneously salvages his human dignity that he need not feel like a needy dependent. Regardless, the Rabbis generally advised giving no more than 1/5 of one's income toward charity, so that one does not oneself become financially dependent on others (Kethuvoth 50a).

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    I keep my approach of not making a mix. Exploiting a needy is not a Tzedaka, when you get a full refund on your money! Otherwise, all the employers are the greatest Tzaddikim as they provide workplaces. In this case, it is only a Tzedaka if you don't need those services, or you employ a needy only masquerading it as a job, but if you do enjoy, you just give a loan, and he pays you back. – Al Berko Oct 18 '18 at 17:37
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    @AlBerko "In this case, it is only a Tzedaka if you don't need those services, or you employ a needy only masquerading it as a job" Can you support that? Loewian brings a source from the Rambam that pretty clearly implies that giving someone a legitimate, non-exploitative job is considered Tzedakah (Sefaria translation: "The greatest level, higher than all the rest, is to fortify a fellow Jew and give him a gift, a loan, form with him a partnership, or find work for him"). Simple reading is that giving the guy a real job is the greatest Tzedakah, not giving some imaginary make-work. – Salmononius2 Oct 18 '18 at 18:52
  • @AlBerko I would certainly think that the person who protects the dignity of the recipient is a greater tzaddik than the one who self righteously diminishes him. But obviously exploiting someone for his own benefit (whether to feel self righteous or for monetary gain) is not a moral ideal. – Loewian Oct 18 '18 at 20:33
  • Good points here made, I haven't really ended their dependency on charity, they could still need more if hardships continue, I've tried helping them by drumming up their business a bit but to no avail as well. – tekiegreg Oct 23 '18 at 19:21
  • To @AlBerko kinda why I'm torn on it too, I didn't need their services at the time (but have an ongoing occasional need), and I'm not "exploiting" in that I'm not buying their rates below their fair market, I usually cut this deal at their usual rates... – tekiegreg Oct 29 '18 at 19:14
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In my understanding:

  1. Basically, you give those people a loan, not Tzedakah. Although giving a loan to a Jew is a Mitzvah on its own, it is not [technically] a Tzedakah as you're paid back the whole amount.

  2. Classically, Tzedakkah is associated with free giving, not getting anything back, and the less you get back, the "greater" is the Tzedaka.

  3. What you refer to is the notion that the less ashamed the needy is, the greater is the Mitzvah. We assume that one is ashamed when accepting free gifts (Tzedakah) from others, so when one feels like he pays back, that cancels the shame and makes the Mitzvah "perfect"

  4. We don't really have a tradition of comparing degrees of Mitzvot, as we don't know the tariffs: it can be a small hassle for you but a huge matter for the needy or the vice verse.

  • Go read the pesukim that talk about tzedakah. Loaning is still a form of tzedakah. – DonielF Oct 18 '18 at 11:56
  • @doniel השב תשיב לו את העבוט כבא השמש ושכב בשלמתו וברכך ולך תהיה צדקה לפני יהוה אלהיך – Double AA Oct 18 '18 at 14:18
  • @DoubleAA That too. I was referring more to פתח תפתח והעבט תעביטנו, but your passuk much more clearly gets the point across. – DonielF Oct 18 '18 at 14:24
  • @DonielF What's your point? You agree that that's a loan we're talking but add that it is a distant form of Tzedaka or disagree that that's a loan? – Al Berko Oct 18 '18 at 17:39
  • @DoubleAA THis Pasuk speaks about a פקדון. Where do you see a פקדון here? – Al Berko Oct 18 '18 at 17:39

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