Encountering the needy on the streets can be difficult and uncomfortable, but that should not prevent us from doing what is demanded of us. Here are 5 things to keep in mind.

1. You can always give something. 

Lacking spare change does not exempt an individual from giving tzedakah. The Jewish notion of giving is far more expansive than simply giving money. The Rambam explains, “If a poor person asks one for a donation and he has nothing to give him, he should appease him with words” (MT, Matnot Aniyiim 10:5). A smile or even an encouraging word can potentially be worth more than money, as the Talmud teaches, “He who gives a small coin to a poor man receives six blessings, and he who speaks to him words of cheer receives eleven blessings” (Bava Batra 9b). Rabbi Joseph Telushkin suggests that we should be generous with our time, not just with our money. Acknowledging their existence, affirming their humanity, and opening our hearts is a valid form of tzedakah.

2. You never lose when you give. 

The only person who truly loses out is the one who fails to give. “More than what a householder does for the poor, the poor man does from the householder” (Leviticus Rabbah 34:9). In an interconnected universe, showing compassion to one in need will ultimately come back to us. When we help others we help ourselves. If we are merciful to others, we will become worthy of mercy, which will be extended to us and our descendants (Shulchan Arukh, Yoreh Deah 247:3). The Rambam adds, “A person will never become impoverished from giving charity. No harm nor damage will ever be caused because of charity…Everyone who is merciful evokes mercy from others” (MT, Matnot Aniyiim 10:2). It’s true your wallet will be lighter after you give, but you will receive something far greater in return. 

3. Have the right intention. 

Rabbi Lord Jonathan Sacks believes, “What matters is not how much you give, but how you do so.” The Talmud goes so far as to say that its preferable for one not to give charity at all than for him to give in an undesirable manner (Chagigah 5a). Humiliating the beggar is a form of bloodshed (Bava Mezia 58b). The Rambam adds, “Whenever a person gives charity to a poor person with an unpleasant countenance and with his face buried in the earth, he loses and destroys his merit even if he gives him 1000 gold pieces. Instead, he should give him with a pleasant countenance and with happiness, commiserating with him about his troubles” (MT, Matnot Aniyim 10:4). The laws of tzedakah are attempting to foster a sense of compassion, therefore its better to give less money frequently than a lot of money less frequently. It takes repetition to alter our nature.

4. Do not look for excuses. 

Wondering what the beggar will do with the money is perhaps the biggest inhibitor for giving. “I’m not giving him anything, he will just use it for drugs or alcohol” is a common refrain that helps alleviate a sense of guilt when we don’t want to give. Jewish law actually prohibits one from wasting time investigating whether the person is telling the truth when he or she pleads, “I’m hungry”. Instead we provide assistance immediately. Try to imagine a time when you needed help, would you have wanted valuable time wasted on the person deliberating whether your intentions were truthful? Doubtful. Therefore we should treat others with the same respect we demand.

5. Be creative. 

Even when you have money to give, always seek the best way to use it. On a hot summer day perhaps look to buy something refreshing. In the winter months, maybe buy a cheap pair of gloves or a hat. The Rambam states, “We are commanded to give a poor person according to what he lacks. If he lacks clothes, we should clothe him. If he lacks household utensils, we should purchase them for him” (MT Matnot Aniyiim 7:3). Just throwing money into a cup is quick and easy, but taking the time to evaluate the real needs of the person is always more beneficial. As the Rambam famously said, “Give a man a fish and you will feed him for a day; teach a man how to fish you feed him for a lifetime.”