In a daring and optimistic passage, the rabbis describe the Divine assistance 1 received by those who make even the smallest gesture of repentance:
Yassa said: The Holy One, blessed be He, said to Israel: My children, make for Me an opening of repentance no bigger than the point of a needle, and I will widen it for you into openings through which wagons and carriages can pass. (Shir HaShirim Rabbah 5:3)
The Gaon of Vilna 2 focused on the odd language of this passage, which seems to be built upon a mixed metaphor: When referring to the eye of a needle, it would be more appropriate to use any of the words that denote a small gap, crack or hole. Instead, the word used is petach (opening), which is most commonly associated with an architectural gap such as a door or window. Alternatively, the contrast might have been drawn between the hole a pin leaves in a garment, rather than the eye of the needle, as compared to the wide gap created when a door is opened. The Gaon learned a very deep and significant lesson regarding repentance from the peculiar wording of this passage:
Sometimes, a small hole is of no significance. For example, when dough is left to rise, one may poke a hole in it that causes the dough to collapse, but the retreat is only temporary; soon enough, the dough will rise even higher than before. On the other hand, if one makes a hole in a garment – the hole is clear and permanent. The Gaon taught, based on this difference, that although God recognizes even the smallest gesture of repentance and responds with great largess, man’s gesture must be real, and not merely a fleeting, halfhearted gesture that leaves no impression on our own inner world.
The examples used by the Vilna Gaon to illustrate this teaching seem far from haphazard or coincidental. The first image, of dough as it rises, is an image familiar to readers of the Talmud as a metaphor for the evil inclination.3 As dough becomes leavened, it expands and rises in a manner analogous to the human ego. Like the yeast in the mixture, sin draws all the other ingredients that comprise the human personality into the inflated sense of self-importance and self-sufficiency upon which the evil inclination feeds. Sticking a needle into the evil inclination, like poking a finger into a batch of rising dough, is a futile gesture; it makes a very temporary impression. This, the Gaon teaches us, is not the sort of repentant gesture that will stir God to come to our aid, to meet us along our path to repentance and guide us toward the light. Simply poking at the growing, festering mixture as it expands and rises actually helps the yeast work more effectively; this is not real teshuva.
On the other hand, a hole made in a garment is qualitatively unlike a hole in rising dough; it is permanent, discernible – a proper petach or opening. This second image employed by the Gaon refers to a “beged,” a word rooted in the Hebrew verb begidah, betrayal: The first clothing appeared after Adam and Eve ate from the forbidden tree and became suddenly aware of their nakedness. The clothing worn to cover their innocence is, therefore, both a consequence of sin and a sign of their rebellion, their betrayal of the trust God had placed in them, and their loss of innocence.
The fight against sin is a difficult battle, and the message the Vilna Gaon hoped to convey in this teaching is that we must be sincere, and make a real and discernible effort to change. Lip service or a bland poke at our own puffed-up egos will not suffice to convince God to come to our aid. Only when we feel the consequences of our own sin upon our shoulders, only when we become aware of how we have clothed ourselves in self-justification and continue to glorify our own rebellion – only when we make a hole in the garments of sin with which we cloak ourselves will we be capable of breaking through and tapping into God’s mercy. In a way, we may compare this hole to the tear a mourner makes in his or her garment, expressing a sense of loss and irreparable damage. And just as the torn garment cannot truly express the grief and pain of losing a loved one, the hole we make in our “clothing of sin” cannot fully express the remorse and shame that is the core of teshuva. Even so, just as the smallest tear is a permanent sign of mourning, so too the smallest hole in our tightly-woven web of ego and self-deception is guaranteed to arouse God’s Mercy. Even a hole the size of a pinhead becomes the starting point for a new relationship with God. Through that small but permanent petach, a world of teshuva is born.
 Also see Shabbat 104a. ↩
 Liqutei HaGra m’Vilna, Moadim p. 252f. ↩
 Talmud Bavli, Brachot 17a. ↩