There are many ways to give charity. Even though all gifts to the poor are considered charity, there are nevertheless different levels of giving. The best of all is to help a person who lost his livelihood to find work, or to lend him money so he can build up his own livelihood and not need to collect donations. The lowest of all levels is to give begrudgingly.

There are eight levels of charity, each higher than the other: (1) The highest level of all is to help a Jew who became poor by giving him a gift or loan, entering into a [business] partnership with him, or finding him work to strengthen him so he will not need to ask others [for donations]…. (2) A level below this is giving charity to the poor without knowing to whom one gave and without the poor person knowing from whom he received, for this is a mitzva [done] for its own sake…. Putting money in a tzedaka box is similar to this…. (3) Lower than this is where the giver knows to whom he is giving, but the poor person does not know from whom he received…. (4) Lower than this is where the poor knows from whom he received but the giver does not know to whom he is giving…to avoid the poor becoming embarrassed. (5) Lower than this is giving the poor person before he asks. (6) Lower than this is giving him after he asks. (7) Lower than this is giving less than appropriate, but giving it with a pleasant smile. (8) Lower than this is giving begrudgingly. (Rambam, Mishneh Torah, Hilkhot Matnot Ani’im 10:7–14)

Further reading: For more on the greatness of charity, see A Concise Guide to the Sages, pp. 240, 245, 426, 457.

The best type of charity is to support the poor with dignity. Even though it does not appear to be charity, finding a job for someone who is having difficulty finding work, or buying merchandise from someone having difficulty selling it is a high level of charity. However, if someone can work but just does not want to, there is no need to feel sorry for him and give him charity.

There is a type of charity that does not appear like charity, but, before the Holy One, blessed be He, it is considered an excellent form of charity. One example is if a poor person has an object for sale or [is selling] a book that people don’t want to buy – and a person buys it from him. Another example is if a poor person wants to write [a mezuza, tefillin, or a sefer Torah] but people do not want to hire him – and someone hires him. There is no better charity [than this]: He works at writing and you give him profit. But if you see a person who could learn and understand, or a scribe who could write, but they do not want to learn or write – if you give them charity, I would consider this [a fulfillment of the verse]: “[He hoped for justice, but behold, corruption;] for righteousness (tzedaka), but behold, outcry (tze’aka)” (Isaiah 5:7). (Rabbi Yehuda HeĤasid, Sefer Ĥasidim 1035)

There are two complementary types of charity. One is fixed and organized, and another stems from compassion. God gave us many mitzvot to perform acts of kindness so the poor are not dependent on generosity of the rich alone. However, a rich person must also open up his heart and give out of compassion, not only because he is commanded to give. The Torah ensures that the needs of the poor are fully taken care of through a combination of two elements: (1) fear of God, which arouses a person’s feelings to give to the poor; and (2) a sense of obligation and acceptance of the “the yoke of Heaven,” which requires a person to give, irrespective of his feelings. When charity is given as a holy obligation, a poor person will not experience a feeling of shame, for he receives the gift from God Himself.

The advantage of fixed, obligatory charity:

This type of charity, where a person regularly donates a tenth of his income, becomes for the donor a holy obligation, rooted extremely deeply in his consciousness. Its value is immeasurably greater than an act of kindness done out of spontaneous inspiration, that is fleeting and abrupt.

Further reading: For the laws of tithing income and charity in general, see A Concise Guide to Halakha, p. 615.

Fixed and regular charity, anchored in a variety of mitzva obligations, is a comprehensive response to the needs of the poor:

It is obvious that [donating a tenth of one’s income] is not sufficient to fulfill “the commandments of the Lord are clear” (Psalms 19:9). Indeed the Torah writes: “You shall open your hand to him” (Deuteronomy 15:8) – that you should open it and open it again [when new needs arise]. You should never be stingy and close your hand and heart to your impoverished brother! But the Holy One, blessed be He, in His great mercy, did not leave the fate of his poor, widows, and orphans in the hands of these fleeting feelings of kindness. Through [a number of halakhic obligations] – the laws of the Jubilee Year, the Sabbatical Year, the prohibition against charging interest on a loan, tithes given to the poor, the unharvested portion of a field left to the poor, and the forgotten sheaves and dropped stalks [likewise] left to the poor – the Holy One, blessed be He, mixed kindness with fear of God and transformed the concern for taking care of the unfortunate and tending to their needs into an unavoidable holy obligation. Only through both of these together, combining fear of Heaven with acceptance of the yoke of Heaven, will it be possible to provide proper relief from poverty, suffering, and destitution.

One who gives charity as a mitzva actually gives his gift to God and the poor receives it from God:

Just as the combination of love mixed with fear [of Heaven] ensures that charitable donations are not dependent on personal inspiration or limited to the giver’s passing mood, so too, the recipient is also protected through this from the shame and indignity of having to stretch out his hand [and collect charity]. When a Jew receives charity from his fellow Jew, the gift doesn’t demean him – for it is not his gift to the poor…. The poor does not receive his sustenance from the human giver, but, rather, directly from the full and open hands of the Holy One, blessed be He. (Rabbi Samson Raphael Hirsch, Bema’agalei Shana, part 2, p. 100)