Boldness:

1. One kind of boldness is thoroughly evil. This is the unashamed self-assertiveness of arrogant people. For `the bold-faced will go to hell' (Avoth 5:25) and Abraham preferred exile rather than hell as the punishment for the sins of the Jewish people. All other sins are punished with exile, but the penalty for this kind of brazen arrogance is still Gehinnom. On the other hand, there is another kind of forcefulness which is essential for anyone who wants to come closer to God. It is impossible to draw closer to the Tzaddikim and sanctify oneself without it. It entails a certain firmness, determination and initiative. This is the quality the sages referred to when they said, `Be bold as a leopard' (Avoth 5:24). The people who oppose those who are truly righteous and who put every kind of obstacle in their way have a brazen arrogance which is `royalty without a crown.' Whoever chooses life and truth needs the other kind of forcefulness in order to overcome these obstacles. His opponents have set their jaws firmly against him, and therefore he needs to set himself equally firmly against them. Only with determination is it possible to enter the gates of holiness (22:11).
2. This determination and forcefulness are also necessary in the fight against oneself -- or rather, against the brazen arrogance of the body, which is itself so forceful when it comes to satisfying its own desires and has no sense of shame before the Almighty. The arrogance of the body makes it impossible for the soul to come down and draw closer to it in order to communicate something of her own spiritual perceptions. The soul has constant contact with the highest spiritual levels, but the body does not have an inkling of any of this because of its dogged involvement with its own impulses. One should take pity on the flesh of one's body and break its dogged pursuit of desire. Then the soul will be able to draw closer and give the body a share in her own spiritual visions and perceptions. To stand up to this arrogance of the body requires the other, holy forcefulness and determination. The way to assert the spiritual power of the soul is with holy sounds -- the sound of prayer and song, the sound of crying and sighing before God, the sound of the shofar or the sound of the voice of the true Tzaddik, and all the other holy sounds, even the sound of the jingling of coins in a charity box! These holy sounds have the power to break the arrogance of the body (Ibid.).
3. But at times a person may be on such a low level and his body so far removed from his soul that even when he groans and cries out to God the body does not hear the sound at all. It is so far removed from the soul that it hears only a confused and indistinct echo. This is because as soon as a holy sound is heard, it arouses the forces of the Other Side, and they are the source of the confused noise. Such a person may even hear the voice of the Tzaddik himself, but he does not hear the essence of his voice, only an indistinct noise, and the arrogance of the body remains unbroken. The body needs to be trained to hear the voice of the soul. It must be pressed into service by performing the practical mitzvot. And to hear the voice of the Tzaddik, the body must be made to participate in practical activities on his behalf. This is the way to train the body to listen to the voice of the sage and to the groaning and crying of the person himself. In the end, the arrogance of the body will be broken (Ibid. 7,8).
4. The way to attain this firmness and determination in pursuit of the holy is through joy. Joy and happiness are the main source of strength for one who wants to draw closer to God and serve Him. `For the joy of the Lord is your strength' (Nehemiah 8:10) (Ibid. 9).
5. Boldness is essential if you want to acquire Torah. You must be `bold as a leopard' to resist the people who put obstacles in your way. You must not be ashamed if they mock you. The bolder you are, the more you will find new horizons in Torah. But a person whose boldness stems from arrogance will not discover truly original Torah concepts. The Torah he receives will be drawn from the forces of the Other Side. To be bold in a positive sense in pursuit of the holy is part of the very essence of prayer -- and the level of Torah a person attains with his boldness will bring him to a corresponding level of prayer. It takes a certain daring, and even `impudence' to stand before God and ask Him for what we need, including even miracles. A person who feels ashamed when he thinks of God's greatness and his own inadequacies and failings will never be able to open his mouth at all. This is why it takes boldness to pray. The more firm and determined a person is in the face of the opposition, the higher the levels of Torah and prayer he will attain (30:8).
6. The bold have no share in Torah. And only the bold have a share. Those whose boldness is arrogance will have no share. Only those who are bold and determined for the sake of holiness will have a share (Ibid.).
7. People may mock at you or put obstacles in your way. But don't allow yourself to be put off by them, and don't become shy and timid. You may think they are better than you or on a higher level. It may even be true and perhaps they really are on a higher level. Even so, as long as your own motive is for the sake of Heaven you must be firm and bold in the face of those who are confusing you and keeping you from the path of life. This is the only way you will attain holiness. Even with the Rav himself you need to be bold. Don't be afraid to talk about anything you need to discuss with him. It is no good to be shy, for `one who is shy will never learn' (Avoth 2:6). The reason why some people are closer to the Rav than others is only because they took the initiative and therefore the Rav speaks with them more (171).