My grandfather always gave beggars a coin, and taught me that it is better to give before you are asked. I am now realizing that many of his sayings were actually based on Jewish wisdom, and am researching the sources. Is there something about giving without being asked?

Answer:

Your grandfather was a mystic, even if he didn’t know it.

Giving tzedakah is always a good thing to do, but there is an extra advantage to charity when you give it without being asked.

The obvious reason is because it minimizes the shame and discomfort of the receiver, and is especially helpful for the person who is in need but is too embarrassed to ask at all. But there is a deeper, spiritual advantage as well.

When the giver initiates a donation, it arouses more Divine kindness than when you respond to a request to give. This is illustrated by the fact that G‑d’s name, the name that denotes Divine kindness, Yud-Heh-Vav-Heh י-ה-ו-ה, is recreated when you give tzedakah.

The coin you give resembles the Yud (י). The five fingers of your giving hand represent the Hey (ה), the fifth letter of the Hebrew alphabet. The arm reaching out to give resembles the Vav (ו). And the five fingers of the receiving hand represent the final Hey (ה).

This name of G‑d is extremely powerful; it is through these four letters that all blessings flow into our world. When we give charity, we spell out these letters and invite G‑d’s light into our lives.

But to spell G‑d’s name correctly, you need to initiate the giving. If you wait for the poor man to stretch out his hand to you, it still generates blessings, but the letters of G‑d’s name are jumbled, and the reciprocal Divine kindness is therefore delayed.

That’s why your grandfather didn’t wait for the needy to come to him; a proactive giver gets G‑d’s name the right way up. And that's why he lived such a blessed life. When you give unsolicited gifts, you receive unsolicited blessings from above, far more than you could have asked for.

Sources:

Baal Shem Tov al Hatorah Reeh 8.