“You shall surely give him, and do not let your heart sink when you give him, because since you have done this thing, HaShem your G-d will bless you in all your actions and in all your activities.” [15:10]

The Torah expresses that one will surely do something by repeating the word; in this case, regarding charity, “surely give” is “nason teeten,” which translates word for word as “[you] give, will give.” Rashi, Rabbi Shlomo Yitzchaki, says that this should be understood as encompassing the repetition found in the words, and means one should give even 100 times. And the Torah says “to him,” that we must give charity repeatedly even to the same person.

The Mishnah in the Chapters of the Fathers 3:19 says, “and all is according to the abundance of the action.” Maimonides comments that “levels of elevation do not reach a person through the greatness of one act, so much as through an abundantly large number of acts.” As much as one great selfless act can have a profound impact on a person and change him or her for the better, 100 smaller deeds will cumulatively have an even larger influence.

The Chofetz Chaim, Rabbi Yisrael Meyer HaCohen Kagan, says that this explains how we should approach the obligation to give Tzedakah, charity. He says it is better for an individual if he or she gives 100 individual dollars to 100 poor people, than all $100 to one person. Giving repeatedly accustoms a person to fighting and beating his miserly inclinations 100 times, and it becomes easier to win in the future. Giving Tzedakah eventually becomes a completely natural act, because one has become accustomed to giving by doing so such a large number of times. This is the self-improvement that the Torah wants from us.

There is an implied criticism here against fulfilling our charitable actions by placing a large sum of money into a fund, and then allowing the directors of the fund to handle the disbursements without further involvement by the donor. The Chofetz Chaim compared this to a real-life situation in his town of Radin, Poland. He lived at the time when the town first purchased an electrical generator, and wired all the houses and courtyards with electric lighting. Obviously, electric lighting is a big improvement over candles, oil lamps, and torches—but one evening, something broke within the machine and darkness descended upon the entire town. All of the houses and streets, and even the synagogue, were dark.

Rabbi Kagan pointed out that before they had electricity, every house had a kerosene light. If one particular house ran out of kerosene, or the wick burnt away, or the glass broke, only that one house would be dark. But when everyone became dependent upon one machine, darkness spread over the entire city when that machine stopped working.

It is certainly more inconvenient to receive people individually, or to respond to their mailings, but that is the point. If people give individually, then if a particular organization, institution or impoverished family is turned away by a few donors, the institution or family can nonetheless find sustenance by turning to others. If everything is placed in hands of a few designated representatives, however, then if those representatives are unresponsive to a particular appeal, then the entire city loses the merit of supporting that poor family or Torah institution—and the whole city is darker as a result.

So when appeals come our way, let us learn to respond individually, to think as individuals, and to grow through our own charity!