"A year which is meager in its beginning becomes rich towards the end." Rashi comments on this saying of Chazal: "Where Jews see themselves as poor on Rosh Hashonoh, regarding pleading and prayer..." When one regards himself as unworthy, this in itself enables him to pass the Day of Judgment [safely]. Chazal also say, "The more one sees himself as unworthy and lowly on Rosh Hashonoh, the better.
We must try to understand why the attitude of self effacement is so beneficial in experiencing Rosh Hashonoh. Don't we know already that the judgment is an accounting of one's deeds? What significance, then, can the approach of poverty [of merit] affect the very judgment of Rosh Hashonoh?
In order to understand this, we must contemplate the character of the judgment on Rosh Hashonoh. It is known that the judgment of actions is in the world of the future, when a person stands before the Heavenly tribunal. What then is the nature of the judgment of Rosh Hashonoh?
The answer is that the judgment does not only include one's deeds but reviews the person in his entirety, in his essence. Where is he `holding'; how does he figure in the whole picture of the world? Is he firmly implanted in materialism or in spirituality? This is the meaning of the Rambam who determines that the judgment of Rosh Hashonoh is not quantitative of one's mitzvos but lies in the quality thereof. How much did a person improve himself through the performance of those mitzvos? To what extent did they affect him internally as a person?
This insight also carries over to the fact that these are days of rotzon, good will and appeasement. We usually relegate this to the good will of Hashem towards us, but it has an opposite interpretation as well - the good will of a person himself, that is, where his own will lies. Do his interests and desires lie in the sea of self indulgence or does his inner essence strive to ascend and be bathed in purity?
Now we can begin to understand why the emotion of insufficiency and poverty are so important on Rosh Hashonoh. The very feeling of insignificance and lack of worth are more effective in transforming one's inner essence. When a person feels his inadequacy in standing before Hashem, the materialistic component of his character disintegrates and disappears and he stands in his judgment as a new man, a spiritual being, and this reality is a sure guarantee for a favorable judgment.
"Like poor and indigent ones do we knock upon Your doors. Please do not reject us empty-handed before You."