Adapted from: Beis Halevi on Bitachon by Rabbi David Sutton

One is obligated by the Torah to give charity, but what is not well known is that the Torah also tells us how one should give charity.

Rabbeinu Yonah (Shaarei Teshuvah 3:35) explains that to achieve generosity, it is not enough to just try to give more money; rather, one must work on developing a generous heart.

Giving charity both generously and with happy feelings is not just an advisable idea; it is part of the Torah obligation!

But how does one achieve this, as it is very hard to part with hard-earned money?

The answer, as Beis HaLevi teaches, is through bitachon. One who has bitachon knows that his money is all a gift from Hashem. It is not a result of his hard work, but rather of Hashem’s kindness, and is therefore truly His. Such a person does not find it difficult to part from his money; he gives generously and happily, trusting Hashem to keep His word, and repay him for his deed.

And there is another important aspect to giving charity.

The Gemara (Bava Basra 10a) states that on Rosh Hashanah, Hashem determines the amount a person is going to earn, as well as the amount he is going to lose. If one merits, the money he is destined to lose will go for charitable causes; if he does not merit, the money will end up in the hands of unworthy people.

Thus, the amount of money one is destined to lose is already decreed in the beginning of the year. However, it is up to the person to decide how he will part from the money.

The Gemara proves this from a story. R’ Yochanan ben Zakkai once dreamt that his nephews were going to lose 700 dinar — a very large sum of money — during the coming year. R’ Yochanan implored them to donate significant sums to charity. They heeded his advice, and they donated a total of 683 dinar.

On Erev Yom Kippur, government officials came to collect 17 dinar in tax money from R’ Yochanan’s nephews. They were very frightened, afraid that the government would then be demanding more.

R’ Yochanan assured them that they had nothing to fear. He informed them of his dream, and explained that by donating 683 dinar to charity, they reduced the decree to just 17 dinar, and so this was all they were going to have to pay.

The Chofetz Chaim asks: Why is it necessary to have two different decrees — how much one will gain and how much one will lose? Why doesn’t Hashem simply decree how much one will earn in total? Instead of decreeing, for example, that a person will earn $200,000 and lose $20,000, why doesn’t Hashem simply decree that he will earn $180,000?

The Chofetz Chaim explains that as a result of one’s sins, one is deserving of punishment. Hashem therefore issues two separate decrees for our benefit, so we can earn atonement without enduring severe calamity. Through these two separate decrees, one can “redeem” his punishment through financial losses. If he simply made less money, the decrease would not count as a “redemption” because he would not feel the pain of actually losing it. By first decreeing that the person should earn a certain amount and arranging that he lose some of it, the loss can serve as his punishment for his sins, in lieu of something more severe.

The Chofetz Chaim adds that, as stated in the Gemara, not only does the loss of money serve as a protection from more severe punishment, giving to charity has the same effect. Thus, charity offers a double benefit; it has the effect of reducing the amount of money one is destined to lose and, secondly, it is a precious mitzvah, for which we will be richly rewarded.

Internalizing this concept makes the mitzvah of giving charity not only a great mitzvah, but a positive experience as well.