“Yesh Hevel (There is a vanity) done upon the earth: there are tzaddikim to whom it happens according to the deeds of the wicked, and there are wicked men to whom it happens according to the deeds of the tzaddikim.” (Ecclesiastes 8:14)

The explanation is as follows: Hevel is the hevel -breath of the mouth that comes from the throat, from the sighs that one sighs; each person commensurate with his level, [as in,] “tzaddikim will go,” and “sinners will stumble” (Hoshea 14:10).

There is one who was wicked all his days, but sighs and groans over the past. And there is, God forbid, one who was originally righteous, but regrets the former [deeds] and also groans and sighs.

Now behold, there are two ropes: the rope of holiness, and counter to it, of impurity. Yet the choice is free. A person who sanctifies himself, binds himself with the rope of holiness. Conversely, God forbid, a person who defiles himself, binds himself with the rope of impurity.

And behold, groaning and sighing are an aspect of death in body and soul. In body, as our Sages teach: Sighing breaks a man’s body (Berakhot 58b). And also in soul, for known is that which is written (Psalms 104:29), “When You increase their ruach -breath, they perish.” This is because prior to death, “their ruach -breath” increases and then “they perish.”

The same applies to groaning and sighing. If you investigate and observe how it is drawn to the throat, [you will see that] it is an aspect of “toSeiPh (You increase) their ruach -breath.” For a short while his ruach -breath increases, and but a minute later he [might] perish and be tei’aSeiPh (gathered up).

Therefore, when one groans and sighs over the sins he has committed, and wants to return in repentance, then with this sigh he perishes and is gathered up from the evil that was in his hands, as in, “When You increase their ruach -breath, they perish.” And he becomes attached to the rope of holiness.

The reverse is also true, God forbid. When one groans and sighs over the good which he has performed, and wants to attach himself to impurity, then his holy ruach -breath perishes and is gathered up. And he becomes attached to the rope of impurity.

This is the meaning of [the opening verse]: **There is hevel—**That is, the hevel -breath of the mouth from the groan and the sigh which he groans and sighs.

**there are tzaddikim—**They regret the former [deeds], and hevel -breath emerges from their mouths from the sighing.

**to whom it happens according to the deeds of the wicked—**This is because they become attached to the Other Side and the impure.

**and there are wicked men—**They groan and sigh, and from the hevel -breath that emerges from their mouth:

**to whom it happens according to the deeds of the tzaddikim—**This is because they separate from the impure and become attached to holiness.

The general principle is this: “[God made] one to contrast the other” (Ecclesiastes 7:14), and a person must get vitality from one or the other of the two ropes. And, no sooner is he separated from one rope, than he becomes attached to the rope which contrasts it.

It is therefore good to become accustomed to sigh over one’s bad deeds, and to yearn and long, in the midst of one’s sighing, to return to God. For through this sighing, one separates from the rope of impurity and becomes attached to the rope of holiness, as mentioned above.

In addition, I found a manuscript from [Rebbe Nachman’s] students on this topic, in which the tremendous value of the sigh of holiness is explained in greater detail. It is explained there that the sigh which a person sighs over his sins or over his lack of spiritual perception, is more beneficial than many acts of mortification and fasts. This is because a fast breaks only the body, but with a sigh one breaks the whole body and also transforms his soul and life-force from evil to good.

For a person’s hevel -breath is a chevel (rope) that binds the upper soul to the place of its root—to good, or God forbid, the opposite. And when he sighs, he is in the aspect of “When You increase their ruach -breath, they perish.” At that point, he separates from the rope to which he was originally bound and becomes bound to another rope, commensurate with the sigh….