We are obligated to feel as if there is no obligation at all.
One of the many laws in Mishpatim is the mitzvah to provide interest-free loans to those in need: Im kesef talveh es ami (Sh’mos 22:24).
At first glance, this may not seem like a command, as the Hebrew word “im” usually means “if,” implying something optional (“If you lend money to My people…”). However, Rashi comments that, in this verse, “im” means “when,” establishing the providing of financial assistance as a formal obligation (“When you lend money to My people…”).
The question is glaring: Why did the Torah introduce this mitzvah with a word that usually connotes something voluntary, if in reality the intention was to describe something required?
The Maharal (in Gur Aryeh) offers a beautiful explanation. While it is true that helping others is an official Torah commandment, one should not perform this mitzvah with such a mindset. Unlike shaking a lulav or blowing the shofar, which one does for no other reason than “Hashem said so,” charity and acts of kindness must be done out of a sense of compassion. They should not feel like technical responsibilities that one needs to “check off” to just fulfill the mitzvah. Chesed should seem “optional” in the sense that we are choosing to do it out of the goodness of our hearts. When we feel the pain of a brother or sister, we should not need to be commanded to leap to provide aid; we should naturally feel the desire to help out.
By introducing the command of helping others with the word im, the Torah is teaching us how to become more sensitive: When carrying out the obligation of charity, don’t view it as an obligation at all. Instead, try to empathize and connect with the difficulties of others, to the point where providing assistance is the obvious choice.
We may not feel this generosity intuitively. Fortunately, the act of giving tzedakah itself was designed to transform us into more caring people. In general, the actions we do influence our feelings (Sefer HaChinuch, Mitzvah 16). For this reason, it is preferable to give $1 to 1,000 people in need, rather than give a lump sum donation of $1,000 to a single recipient (Rambam, Avos 3:15). From an interpersonal perspective, you would have expected that it would be better to provide significant help to one person, instead of delivering pocket-change to the masses. However, with an eye toward one’s own character development, only an abundance of consistent giving can shape a person into a compassionate benefactor.
Perhaps, at the beginning, our acts of kindness will be a “when,” something driven by the pressure of religious obligation. The goal, however, is that over time our generosity will become an “if,” inspired by our own internal barometer of compassion. In essence, the true obligation of chesed is only fulfilled when one feels as if there is no obligation at all!