Yom Kippur: Overcoming Self-Doubt & What Rachamim Really Means

By Rav Haggai Londin, translated by Hillel Fendel 

The name of the game is not total victory, but constant progress.

The days leading up to Yom Kippur are not simple. It turns out that of all times, it is specifically during the holy days leading up to the Day of Atonement – precisely when we seek to self-improve and make amends for the bad we have done – that doubts tend to creep up. After all, last year and the year before I asked forgiveness, I prayed deeply, and I promised myself I would not sin – and did it work? Barely! So what's the purpose of all this teshuva (penitence)? How can this Yom Kippur possibly be different than last year's?

The answers depend on where we are psycho-spiritually. If we are in a position of seeking absolute perfection, it very well could be that we will end up despairing and unforgiving of ourselves (in the best case) and of those around us (in the worst case). But if we demand of ourselves not perfection, but rather constant improvement, we will be filled with compassion. To explain:

Our ability to forgive ourselves stems from the trait of compassion. In the modern Western world, this trait is associated with concessions and leniency, which is why people today tend to be quick to forgive themselves for their ethical failings. But in fact, compassion in the Torah's teachings is not at all a matter of leniency. The Sages say, "Whoever says that G-d is One Who makes concessions, may his insides be ceded." This sharp statement simply means that G-d is the G-d of truth, and He cannot be expected to "round out corners." Just as one would not beg his math teacher to agree that 2+2=5, we know that Divine truth must appear in the world.

Rather, we have to understand that the Hebrew word for compassion/pity is rachamim, from the same root as the word for womb, rechem. The womb is the place where the fetus develops before emerging into the world, the place where new life for the future is fashioned. That is to say, the ability to have pity and to forgive, ourselves and others, is the ability to trust. We forgive ourselves not because we wish to be conciliatory and to "give in," but rather because we believe that despite the fact that we, or others, are currently in a "failure," we will yet be strong enough to grow new strengths that will take us to the place we want to be.

Furthermore, the ability to forgive ourselves is the ability to understand that all of reality, including ourselves, advances slowly. There are failures and downturns, but the general direction is towards progress. A mature approach to life knows that there is no such thing as an absolute victory over the conditions that lead us to occasional failure. It understands that there is no such thing as, "From now on I will never stumble again." Rather, we can say, "From now on I will improve a bit more." This enables us to forgive ourselves for our mistakes, large and small, and live with them in the right way. 

This explains why we begin Yom Kippur with the Kol Nidrei prayer. It is here that we say that "the vows, oaths, and the like" – i.e., all the ropes and chains that tie and bind us to our failures of the past year – are all "null and void, non-existing and non-binding." The ability to start again is not a form of naivety, but rather a mature understanding on what a "process" is. There is no such thing as actually reaching the goal – such as "never stumbling again;" rather, what we strive for is to keep on going forward. If this year I succeeded in concentrating during prayers for a total of five minutes more than last year, this is a tremendous achievement that should power my engine and my happiness so that I can go even further in the coming year. The same is true if I succeeded in adding even one extra Torah study hour each week, or in gossiping less. Every improvement is valuable. 

When we say Kol Nidrei, we are born anew; we understand that our failures are just temporary and transient, while our regret and our commitment to change is the stable element in our lives. This is why the introduction to Kol Nidrei includes the declaration, "We permit to pray together with the sinners" – for to sin is something transient, while our souls are stable. 

Extricating the Good From the Bad

This concept of "process" is also manifest in the High Priest's Temple service in the Holy of Holies, which was the central and focal aspect of Yom Kippur throughout the centuries that the Temple stood. The climax of this service was when the High Priest entered the Holy of Holies, the most sacred spot in the world to which even he was not allowed to enter except on this one day a year. There he would offer the incense offering – a mixture of eleven different spice powders, of which ten were very aromatic, while one of them, the levonah, had a very unpleasant smell. Most wondrously, when all the powders were mixed for the incense, even the fragrance of the levonah became pleasing. 

On Yom Kippur, it turns out that when we "bind together" (from the same Aramaic root as ketoret) all the details of life, even the forces of evil become good. In the course of the broad context of life we gradually "sweeten" the bad. We are filled with compassion even for the forces of negativity and work to correct them during the course of our lives.

This year, not unlike other years, we have very much to pray for on the national plane as well. The State of Israel faces great challenges on all fronts: Militarily, sociologically, economically, politically, and certainly spiritually. This coming Yom Kippur, let us stand before our G-d, and before ourselves, and declare courageously our sincere intent to free ourselves of our previous lives, to loosen and free up that which binds us, and to open up to new life, a life of compassion – a life of a new year.