Elul is a time to be especially involved in chesed – lovingkindness. Here are three reasons why.

1. Elul is a time of coming close to G-d.
The 40 days of closeness Hashem showed the people of Israel after the sin of the Golden Calf reawaken every year, from Rosh Chodesh Elul until Yom Kippur. We bring ourselves close to G-d by doing teshuva (repentance); and he in turn breaks down some of the barriers we encounter. In Elul we focus on coming close to G-d. One central way of coming close to G-d is through imitating His Divine mercy and relating to others with chesed. [Rabbi Aryeh Kaplan has pointed out that in spiritual things closeness is measured by similarity, whereas physical closeness is measured by distance. For instance, the two concepts “love” and “chesed” are referred to as close to each other because they are similar. Becoming close to Hashem involves making ourselves as similar to Him as possible. Becoming people of chesed will bring us close to the G-d of chesed.]

2. Elul is a time to do teshuva.
“Act positively in the same areas you sinned in,” is the tenth fundamental aspect of teshuva listed in the first chapter of Rabbeinu Yona's Shaarei Teshuva (1:35). Here are some of his examples: one who sinned through negative speech should now speak words of Torah; one who ran to sin should now run to do mitzvot; one's whose thoughts dwelled on what they shouldn't have should now meditate on Torah; lips that lied should now speak the truth; and one who caused dissent should work at bringing about peace.

Rabbeinu Yona quotes a Midrash in Vayikra Rabbah (21:5) as his source, “R. Natan and R. Acha quoting R. Simon said, 'If you did bundles of sins, do instead bundles of mitzvot.'” It goes on to list a number of examples. R. Simon bases his statement on a verse in Mishlei (24:6), “For you should wage war using 'tachbulot'.” What does “tachbulot” mean? His drasha understands it to be based on the word “chavilot” - bundles, seemingly far away from the simple meaning of the word, tricks or ruses. But his drasha illuminates the simple meaning of the verse. “Wage your war against your evil inclination using trickery by recruiting his agents and turning them against him. He's been using the body's legs to run to aveirot? Recruit them for good and run to mitzvot. He's been using a mouth to speak falsehood and lashon hara? Recruit it for good and speak Torah.”

Doing chesed is a powerful way of recruiting the enemy's forces because it redirects our entire self away from sin and towards good. When we sin we focus on ourselves; when we do chesed we focus on others. Following the verse's war analogy: shifting the whole focus of our being from egocentricity to altruism is like shifting the enemy king's allegiance and transforming him into an ally.

3. Elul is a time to begin working on atonement.
Acts of chesed, teaches Rabbeinu Yonah (Shaarei Teshuva 1:47) can bring about kaparah (atonement) in a pleasant way. Sins that would normally require experiencing yisurin (physical or psychological difficulties) for atonement can be cleansed through doing chesed. This is based on the verse, “Chesed and truth bring about atonement from sin (Mishlei 16:6).” Yom Kippur is the Day of Atonement for many sins, but not all. For some sins atonement only comes through experiencing yisurin that cleanse the person of his sin. Rabbeinu Yonah (Shaarei Teshuva 1:47 and 4:5) develops a two-track approach to atonement.

In one path to atonement the person is passive. He sinned; he did teshuva; then he waits for G-d to cleanse his sin and purify him through the troubles or difficulties that befall him.

However, a person can choose a second track, acheiving atonement by conteracting his sins with its positive counterpart. Desecrating the Divine Name can be cleansed through kiddush Hashem, sanctification of the Divine Name. Publicizing and strengthening truth in the world increases the honor of G-d and atones for the opposite. And selfishness, egocentricity, and self-centeredness can similarly be cleaned through chesed.

Counteracting sin through a corresponding mitzva is part of teshuva (#2 above) – for it redirects our powers from evil to good, sapping our yetzer hara of its resources. But, teaches Rabbeinu Yonah, counteracting sin also helps us achieve atonement after we have done teshuva. Chesed is a core mitzva, and deserves special attention during Elul: it refocuses us, cleanses us, along with bringing us closer to G-d.