"Make every effort to give to [the poor], and do not feel bad about giving. For because of this, the Eternal your God will bless you in all of your endeavors." (Deut. 15:10)
How does God bless one who helps the poor and needy?
One might think it is like this case:
A man lost a wallet containing a $100 while walking downtown. The following morning, he went downtown and picked up a $200 bill on the pavement.
But this is not what the Torah is talking about. This person, even though he found more money than what he lost, is still upset about the original $100 that was lost. He thinks to himself, "If I hadn't lost that first $100, I would have now $300!"
Rather, the blessing the Torah is speaking about is like this case:
A farmer purchased a sack of grain and carried it home by way of his fields. Not realizing there was a small hole in the sack, little by little the grain trickled out. By the time he reached his home, the sack was empty!
Some time later, the farmer passed through his fields. He was shocked to discover that the grain he had unwittingly spilled on his fields had grown into a tremendous wheat crop.
This man will not regret the grain seeds he lost. He realizes that if they hadn't spilled out over his fields, he would not have been blessed with a wonderful crop.
That is what the Torah promises, "Don't feel bad about giving." It is through this very giving that you will be blessed in your endeavors.
(Adapted from Mishlei Yaakov, p. 431)