In Parshat Toldot, Jacob and Esau, like so many other biblical brothers, are in conflict. From the womb, the two struggle with each other, leading God to tell their mother, Rebecca, “Two nations are in your womb and two peoples shall come out from your bowels; one people will be stronger than the other people and the elder shall serve the younger.”
Rashi explains that not only will the two be unequal in greatness, but also, “K’she zeh kam, zeh nofel”—“When one arises, the other falls.” For Jacob to succeed, Esau must fail, and vice versa. For some reason, they cannot both thrive. It’s as if the two are trapped in the most simple of economic and game theory setups: the zero-sum game. In a zero-sum game, if I give you five dollars, I’ll have five less while you’ll have five more. Your gain plus my loss—as Jacob’s and Esau’s—must equal zero.
Indeed, we often think in zero-sum terms about donating money. We may believe that a gain for others is a loss to us and therefore hesitate when contemplating tzedakah. In his 14th-century legal code, Arba’ah Turim, Rabbi Yaakov ben Asher addresses the anxiety we feel about whether or not we can afford to give tzedakah by reassuring potential givers that, “A person has never become poor from giving tzedakah and nothing bad or damaging has ever resulted from it.”
Despite our inclination to worry about the loss we might experience from giving, tzedakah is not a zero-sum game. Certainly tzedakah costs the giver something and benefits the recipient. However, there are benefits to the giver as well as to the receiver of tzedakah, and Judaism offers such benefits as reasons to give. According to the midrash in the name of Rabbi Joshua:
More than what a householder does for the poor man, the poor man does for the householder, as Ruth says to Naomi, “The man’s name whom I helped today is Boaz” (Ruth 2:19). It doesn’t say, “Who helped me,” but rather “Whom I helped.”
The midrash points out that Ruth, a poor woman, helped the wealthy landowner Boaz, implying that Boaz benefitted from the opportunity to give tzedakah. Indeed, Jewish tradition suggests several ways in which giving benefits the giver. Tzedakah is described as a way of getting closer to God, for it is through tzedek that God’s presence is seen. The Torah further promises that God will reward those who practice justice and righteousness with long life and inheritance of the land.
Although we may feel some ambivalence about giving tzedakah, the notion that we gain something from the act of giving is likely not foreign to us. We may feel good about giving because we are helping to alleviate suffering or to address inequality and injustice. In fact, we may even derive a more concrete personal benefit from giving away what is ours. Kevin Salwen, author of The Power of Half, describes the positive effect on his family of selling their luxurious Atlanta home and using half of the proceeds to purchase a more modest home while donating the other half: “We essentially traded stuff for togetherness and connectedness. . . . This is the most self-interested thing we have ever done. I’m thrilled that we can help others. I’m blown away by how much it has helped us.”
Thus giving tzedakah can be an experience that benefits not only the recipient but also the giver. Maimonides takes this idea one step further, suggesting that the effect on the giver might actually trump the impact on the recipient. He explains:
When a person gives to an appropriate person one thousand gold pieces at once, he would not be considered at the level of generosity in this one large action as someone who gave one thousand gold coins (one at a time) one thousand times and through each coin was generous, because this multiplies the act of generosity one thousand times and [the trait of generosity] is strengthened in this person, while the other one only had his spirit raised to the awareness to do good once and then stopped.
In other words, Maimonides startlingly concludes, it is better to give less but give it often, even if the impact on each recipient is smaller, rather than giving a large lump sum, which would have a greater impact on the recipient. Why? Because more frequent giving cultivates a generous character in the giver.
This serves as a reminder to us that as important as tzedakah is to bringing less need and greater justice to the world, it also has a profound impact on the person giving it. When we hesitate to give tzedakah, worrying how much we can afford to sacrifice so that others can do better, let us remember that, unlike Jacob and Esau’s zero-sum struggle, tzedakah can be an act that benefits us all.
 Genesis 25:22–23.
 Rashi on Genesis 25:23.
 Tur, Yoreh De’ah 247.
 Leviticus Rabbah 34:9.
 Talmud Bavli Bava Batra 10a referencing Psalm 17:15.
 Deuteronomy 16:20 and elsewhere.
 Nicholas Kristof, “What Could You Live Without?” The New York Times. 24 January 2010: WK12. http://www.nytimes.com/2010/01/24/opinion/24kristof.html
 Rambam, commentary on Pirkei Avot, 3:15.