The pasuk says in this week's parasha Re'eh, עשר תעשר, which the Gemara explains to mean, give ten percent of your earnings to charity and you will become wealthy. Although the pasuk is speaking to a landowner giving ten percent of his crops to charity, Tosafot bring from the Sifreh that the same applies to a businessman giving ten percent of his earnings. The Tur writes in Yoreh De'ah, siman 247, it has been tried and tested, when a person gives tzedaka, he does not lose, rather the opposite happens, he gains wealth and honor from it. Furthermore, it nullifies harsh decrees and saves the person from death.
The Rama is posek that giving tzedaka brings a person wealth and this is the only area in which a person is allowed to tell Hashem he is waiting to see the fruits of his labor. The Chafetz Chaim in his sefer Ahavat Chesed writes the halacha is like this Rama. As with all mitzvot, there are exact details on how to perform them and in order to reap their full rewards, they must be done correctly, and therefore, a person must learn all of the halachot of giving maaser to ensure that he is doing it correctly to reap its benefits
A woman once sent a question to the Imreh Emet regarding maaser. She wrote, my husband makes a minimal parnasa and he is still careful to separate maaser. That maaser, however, comes at the expense of us being able to buy shoes and clothing for our children. Is my husband still obligated to give maaser under those circumstances? The Rebbe replied, when one gives maaser, he must give it with an open heart and when he knows that the money going to tzedaka is not really his, it's much easier to give it with joy. Strictly speaking, you are not obligated to give but there is a segula if you give with an open and happy heart, with a true desire to give, then you fulfill what it says in the pasuk 'let your heart not feel bad when you give' and that pasuk continues and says, because of that type of giving, Hashem will bless you in all of your deeds and in every undertaking. We see from here, one of the requirements to merit the blessing is to give with a happy heart.
Moreover, if we do find somebody giving maaser and not becoming wealthy, there is for sure a great reason that we are not capable of understanding at this point. But we must trust that Hashem is doing it for the absolute best of the person giving. A wealthy man who started becoming careful in giving maaser began losing his wealth at the same time. He went to Rav Eliashiv, z"l, asking how such a thing could happen. The Rabbi replied, it seems that some of your money was earned in a non-kosher way. So long as you were not giving maaser, you did not have the zechut to become cleansed from that severe sin. But now that you began giving, you have become worthy. Hashem is now giving you kapara for all the dishonesty you had in business and that is the greatest chesed He could possibly do for you.
Giving tzedaka is wondrous. It benefits us in both worlds. Let us not only give, but give with a happy heart.
Shabbat Shalom.