Human nature is to desire to be self-sufficient. Most of us are uncomfortable being takers and prefer earning our own keep. If, due to dire circumstances, we find ourselves on the receiving end, our reaction is generally one of mortification.
The Torah is acutely sensitive to the precarious dynamic between patrons and their beneficiaries. The Torah's word for the act of giving to the needy, tzedakah, although commonly translated as "charity," more accurately means "justice." ....
Level Eight: Giving grudgingly, with a sour countenance.
Giving grudgingly is certainly better than not giving at all, ....
Level Seven: Giving less than you can afford, but doing so pleasantly.
The benefit of a friendly response is so powerful that it even offsets the sting of an underwhelming donation. ....
Level Six: Giving generously, but only after being asked.
While it's certainly preferable to be proactive, at the very least, don't give a cold shoulder to those who approach you for help.
Level Five: Giving before you are asked.
Learn to anticipate the needs of others even before they approach you.
Level Four: The recipient knows the giver, but the giver does not know the recipient.
In levels five through eight, the recipient and the giver are both known to each other. So even when the giving is done with utmost sensitivity and happiness to help, theirs is a relationship of superiority: the giver's ego is gratified, and the recipient feels shame and inferiority because of his dependency. ....
Level Three: The giver knows the recipient, but the recipient does not know the giver.
In this level of tzedakah -- which is the converse of Level Four -- the donor's ego has some room to express itself. Since the giver knows who is receiving his bounty, there is room for some sense of one-upmanship or dominance over the receiver. However, the beneficiary is unaware of who the donor is, and so his dignity is preserved. ...
Level Two: Giving anonymously, where the recipient does not know the giver and vice versa.
Receiving mutually anonymous tzedakah takes much of the sting out of being on the receiving end. It is far better when we lend aid to others unconsciously -- when we give ourselves over to others so completely that our egos merge with theirs, and neither is conscious of being in a superior or inferior position. ....
Level One: Helping someone become self-sufficient.
The most basic need of a human being is to feel needed and capable. Thus, the highest form of tzedakah is to help someone find a job or set them up in business. This preserves their dignity, and at the same time transforms them from being a recipient into one with the capacity to give to others. ....
Tzedakah is actually a cycle -- the gifts that we give to others will eventually return to us. Furthermore, G‑d is acutely tuned in to our small acts of goodness and kindness. Our acts of giving stimulate G‑d's blessings to shower down upon all of us, the giver and the receiver alike.