Precisely those who toiled — they are the ones who can see the situation in its proper perspective and to see that there really is reason to be fearsome and alarmed. We are dealing with the cleansing of the intellect and the soul! A decontamination from all the pollution of the body. Once a person has purified himself during the days of Elul, his mind is more lucid and his thought processes are more coherent; subsequently, his vision is also more spiritual. This is why we are afraid of the Day of Judgment.
There are two components to the avodoh of Elul days: the active, physical aspect like blowing the shofar after shacharis every morning and the addition of Mizmor leDovid Hashem Ori. In yeshivos, they also add a slot for the study of mussar before minchah. Everyone keeps these in practice.
The second part is the self introspection — delving inside one's soul and making the necessary resolutions for improvement, for purification, for cleansing of the dirt and the impurities that cling to us through our sins. For the days of Elul are a preparation for the Days of Judgment when all creations will be reviewed for life or death. How can we possibly enter the period of judgment with filth adhering to us? We must somehow purify and prepare ourselves.
It would stand to reason that comes Rosh Hashonoh, those people who were lax in their spiritual awakening and preparation would suddenly be afraid of the Day of Judgment, while those who did spend the month in introspection and groundwork, in cleaning those musty, dirty corners in the chambers of their souls — that they be less anxious, for they had not neglected their preparations.
In reality, however, we see the very opposite. Those who toiled to purify their hearts are the very ones who tremble in fear when Rosh Hashonoh comes around, while the nonchalant ones remain somewhat indifferent; they are serene and confident. Strange, isn't it?
The answer is that those who contemplated are able to see the situation as it truly is. They realize that there are, indeed, grounds to be afraid and to tremble. They have had to cleanse their minds and their souls! To purify themselves! For by washing themselves clean of external filth, their vision has become purer and clearer; it is more spiritual, more acute and sensitized, and they see they have reason to be frightened.
The others who did not cleanse themselves and did not acquire a clearer vision, do not even see what there is to be afraid of because of the judgment.
They tell that on the night of Rosh Hashonoh, when they came to tell the Alter of Kelm ztvk'l that it was time to daven ma'ariv, he was suddenly seized by a great terror. He would begin murmuring to himself in a quaking voice, "Oy, they are already calling me to my judgment!" For all month long he had been preparing himself, purifying himself, and now the time had come and he saw clearly what awaited him.
HaRav Moshe Rosenstein zt'l once asked Maran the Mashgiach of Mir, R' Yeruchom zt'l, how it was possible for the generation of the desert to have gone and made themselves a golden calf. They personally experienced the exodus from Egypt, they personally stood at Har Sinai to receive the Torah and they personally heard Hashem speak to them. How, then, could they thus sin?
He replied: That, my dear man, is the power of the yetzer! And he began tearfully reciting, "For forty years was I wearied with that generation and said that it is a people that errs in its heart and they have not known My ways!"
True, they left Egypt and stood at Har Sinai and yet, despite their exalted spiritual level they still contained a smattering of spiritual pollution which distorted their vision. And it was still possible to say of them that "they have not known My ways."
The Mashgiach also said that the Evil One is an angel, after all, and in order to vanquish and break it, one truly needs a miracle. Without a miracle, one cannot hope to break or change one's own nature.
This is the answer to the major question which we have often encountered. There are many clever people in the world, people with good sense, but they are gentiles . . . How come these gentiles do not begin to think about life, why they were put here in this world and what is the end purpose of it all? They simply do not stop to think. They live their lives out without thinking because they never stopped to purify their souls and are unable to open their eyes. They lack vision and simply cannot see anything.
During the days of Elul, which are days of preparation for Rosh Hashonoh, we must toil to open our spiritual eyes a bit more, every day. Our vision must become more acute by the day. A person must test himself to see if he really cleansed and purified something in his soul. For if he does not feel an intensification of fear from the Day of Judgment, it simply goes to show that he has not removed any layer of film and filth. The more his spiritual eyes are opened, the more it stands to reason that he will see better and realize how much he has to experience trepidation from the upcoming Judgment.