Generally speaking, we find two different and opposite messages in the holy books.
Sometimes we are told how great, special, and beloved to G–d the Jewish people are. At other times we are told how puny and insignificant we are, for our physical world is the lowest of the low compared to all the higher spiritual realms (Tanya, ch. 36), and how low we are on account of our bestial soul’s natural attraction to the physical, never mind our desire to sin (ibid., ch. 29).
Likewise in terms of our generation as a whole: Sometimes we are told how our generation is spiritually lower than all generations that preceded it, comparable to the dead skin at the sole of the foot. But at other times we are told how our generation is superior, for we are the ones to bring the final Redemption.
The same is true of our individual divine service. Some Torah sources convey how infinitely precious every Mitzvah is, and how much is accomplished spiritually every time we learn Torah, and do even the most apparently minor good deed. Other sources make us feel that no matter how much Torah we have learned and how many Mitzvos we have performed, it will always be insignificant when compared with how much more we could have accomplished, or the amount of Torah left to learn, or the number of Mitzvos left to perform, or the amount accomplished by others greater than us today, or by earlier generations.
In some sources we are told that we should recognize our good qualities, while other sources emphasize how we should feel inferior to everyone else.
Some sources put down even the greatest Tzaddik, while others express the inherent greatness of even the greatest rasha (wicked Jew).
Some sources emphasize that it is always possible to do Teshuvah (repentance) for “Nothing can stand in the way of Teshuvah” (cf. Talmud Yerushalmi, Pe’ah 1:1), while other sources imply that one’s Teshuvah is never truly complete (cf. Tanya, ch. 29).
So which is it? Are we supposed to feel high or low, proud or humble, worthy or worthless, special or insignificant?
The answer is both very simple and very complex: It depends. It depends on the person—on his current state, on his environment, his background, and his level. The key is to maintain a balance, and this is accomplished through giving the correct medicine for the correct disease.
This can even be understood in the way a Jew should conduct himself in the secular world:
A rich entrepreneur doesn’t need praise for his business acumen. He needs to be told that only G–d is “the one who gives you strength to perform deeds of might” (Devorim 8:18). The same goes for a brilliant general, or a famous musician.
In contrast, a person starting a small business, a young recruit into the army, or a budding pianist, needs encouragement. He needs to be convinced that G–d really has endowed him with the talents that he needs to succeed. And even if he won’t reach fame and riches, he will make a substantial impact upon others. However, if he compares himself to the people at “the top,” and considers (often rightly) how unlikely it is that he will reach their success, he is liable to feel discouraged, and give up altogether.
The same is true of serving G–d. The Jew who struggles mightily to attend a Minyan, but barely makes it, needs to be praised profusely for his efforts. If he is told that his accomplishments are pitiful, this may well cause him to feel like a failure, which will weaken him so much that he will lose his drive to go to the trouble to attend the Minyan.
Conversely, the Torah scholar who learns all day but starts to let it go to his head, needs to be denigrated. He needs to be made to feel how ignorant he is compared to other scholars, how he is only realizing a minute fraction of his true potential, and how his apparently trivial sins are much worse than the severe infractions of others (see Tanya, end ch. 30).
Moreover, even during the one day a person may experience different moods, and here, too, this advice holds. At one point he feels weak and unaccomplished—then he needs to be uplifted and supported. But later on, after he prays at length, learns in depth, or contributes to Tzedakah in great quantities (or all the above), and considers that most others are not nearly as assiduous, sincere, or generous, he should belittle himself and his good deeds, as explained above.