Mishnah
Mishnah

Musar for Pirkei Avot 2:5

הוּא הָיָה אוֹמֵר, אֵין בּוּר יְרֵא חֵטְא, וְלֹא עַם הָאָרֶץ חָסִיד, וְלֹא הַבַּיְשָׁן לָמֵד, וְלֹא הַקַּפְּדָן מְלַמֵּד, וְלֹא כָל הַמַּרְבֶּה בִסְחוֹרָה מַחְכִּים. וּבְמָקוֹם שֶׁאֵין אֲנָשִׁים, הִשְׁתַּדֵּל לִהְיוֹת אִישׁ:

He was wont to say: "A bur will not fear sin." [A "bur" is one who is "empty" of everything (the Targum of Genesis 47:19 "And the land will not be empty" is "And the land will not be bur.") He is empty even of business acumen and is worse than an "ignoramus"], and an ignoramus cannot be a saint, [but, having business acumen, he can be a fearer of sin], and he who is ashamed will not learn. [Being ashamed to ask lest he be mocked, he will remain with his doubts forever], and the pedant will not teach. [He who is "pedantic" (not forthcoming) with his students when they ask him, will not teach correctly. He must be "open" with them in (the teaching of) halachah], and all who (over) engage in trade will not be wise, [viz. Deuteronomy 30:13: "And it is not across the seas" — Torah is not to be found with those who cross the seas (in trade). (Eruvin 55a)], and in a place where there are no men [to sit at the head and render halachic decisions], strive to be a man.

Orchot Tzadikim

For it is clear that the servant of a king will not abandon the king's command though he bears much shame from everyone who may laugh at him for performing that which his king commanded him. And he who cannot bear the shame in performing the precept and is ashamed to fulfill the command of God — and thus forsakes the path of good out of fear of shame — this kind of shame is very evil. And thus, if he is ashamed to admit the truth, this too is an evil disease. And thus, if he is too shy to rebuke people and command them to do good. And thus if he sits before his teacher and is too ashamed to ask what he does not know, whether it be a small matter or a big matter, such an attitude is very ugly. In these cases Scripture says: "Do not act foolishly by exalting yourself nor by cunningly keeping silent" (Prov. 30:32). And our Sages of Blessed Memory said: "The one who is ashamed (to ask questions) does not learn" (Aboth 2:5). The proper way is never to be ashamed to ask concerning what one does not know whether it be a small matter or a large one. Did you not see that David, King of Israel, said in Psalms 119:46: "And I will speak of Thy testimonies before kings and I shall not be ashamed."
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Mesilat Yesharim

We have already pointed out that this is the most essential of all things for the acquiring of watchfulness, as the Beraitha of Rabbi Pinchas ben Yair states: "Torah brings to watchfulness". Without Torah, one will not reach it at all. This is what our sages said "an ignorant man cannot be pious" (Avot 2:5).
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Mesilat Yesharim

In speech: it was taught explicitly: "one who speaks excessively to a woman brings evil upon himself" (Avot 2:5).
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Mesilat Yesharim

Likewise we learned: "nor do all who engage in much business become wise" (Avot 2:5). The lust for money exposes him to many dangers and weakens his strength with many worries, even after he has attained a great amount as we learned: "one who increases possessions, increases worry" (Avot 2:7). It is lust for money which leads him many times to transgress the mitzvot of the Torah and even the natural precepts of reason.
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Orchot Tzadikim

And you often see people who when they are angry and persist in their wrath, are not conscious of what they are doing and do many things in their anger which they would not do if they were free from anger, for anger draws out the intelligence of a person from within him until his angry deeds multiply and he is plunged into strife and quarrel. Therefore, it is impossible that the wrathful person should be saved from great sins. And so did Elijah say to Rabbi Judah : "Fall not into a passion and you will not sin" (Berakoth 29b). And the Sages said : "By three things is a man known" (Erubin 65b) and one of them is his anger, for when a man is angry his true nature can be recognized. If his wrath is stronger than his wisdom and he does things in the moment of his anger without regard to his wisdom, then you can see the character of his wrath. But if his wisdom is stronger than his anger and he de does not say or do anything when angry that he would not say or do when he is free from anger, then you can see the extent of his wisdom. And the Wise Man said : "Three, the Holy One Blessed be He loves and one of them is he who does not anger" (Pesahim 113b). And our Sages said : "Nor is an impatient person fitted to teach" (Aboth 2:5), for because of his great anger, the pupils fear him too much to ask the things of which they are in doubt lest he be wrathful with them. And even when his pupils do ask the impatient teacher questions he has neither the mind nor the patience to explain to his pupils all that is needed to make the matter clear. Then, too, he will answer questions in anger and thus the pupils will not understand the matter clearly. As for the pupils, it is their duty even when their teacher is angry with them, to ask their questions and listen carefully and not be hurt by the anger of their teacher nor quarrel with him. Concerning such pupils our Sages taught : "So the forcing of wrath bringeth forth strife" (Proverbs 30:33). Any pupil whose teacher is angry with him repeatedly but bears the teacher's wrath in silence will merit to discern between civil and criminal law. And a master said : "There is nothing more difficult than civil and criminal Law" (cf. Berakoth 63b).
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Mesilat Yesharim

However, the factors which cause loss of this trait are all those detriments to the trait of Watchfulness, in addition to lack of proficiency in knowledge of the laws and ethics (Mussarim) as I wrote above. Our sages already stated: "an ignorant man cannot be pious" (Avot 2:5). For one who does not know cannot possibly do. Likewise they taught "great is study in that it brings one to doing" (Kidushin 40b).
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Mesilat Yesharim

The intent is that a person distance and separate from anything which may lead to something which could bring about evil, even though right now it does not cause evil and even though it is not itself evil.
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Mesilat Yesharim

But actual Piety itself requires great depth to understand it correctly. It is based on foundations of great wisdom and utmost rectification of one's deeds, which befits every wise hearted man to pursue. For only the wise can truly attain it, as our sages stated: "an unlearned man cannot be pious" (Avot 2:5).
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Mesilat Yesharim

The first division of deed itself further divides into two subdivisions. The first between man and G-d and the second between man and his fellow.
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Shemirat HaLashon

It is written in Mishlei (9:10): "The beginning of wisdom is the fear of the L-rd." This indicates that the beginning of wisdom for the man who seeks to be wise is to acquire fear of the L-rd. Yet, another verse in Mishlei states (4:7): "The beginning of wisdom is to acquire wisdom." This would seem to indicate that the beginning of all for him who desires to acquire wisdom is to reflect upon wisdom [that is, the wisdom of the Torah]! But, in truth, there is no contradiction. Solomon, may peace be upon him, desired to teach us that both are necessary, that one without the other is not worth anything [(as per the Tanna in Avoth (3:17): "If there is no fear, there is no wisdom; if there is no wisdom, there is no fear")]. That is, if one would seek to place all his toil and reflection upon acquiring fear of the L-rd and think to acquire wisdom afterwards, King Solomon, may peace be upon him, advises us that it is not right to do so. For to acquire fear as befits a Jew, he must seek it as silver, as Scripture states (Mishlei 2:9): "If you seek it as silver, …then you will understand fear of the L-rd." And the seeking of silver is not for one day or one week or one month; but silver is always on his mind. So, the man who wants to acquire fear of the L-rd. He must always reflect upon His greatness and upon the goodness which He confers upon him each day and increase fear of the L-rd in his soul. And if he waits to reflect upon the wisdom of Torah until he becomes a fearer of the L-rd in truth, this will take a long time, so that all of that time that his heart is void of wisdom, his fear is worth nothing. For if there is no wisdom there is no fear, and (Avoth 2:5): "A boor does not fear sin."
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Orchot Tzadikim

And now consider the case of a man who must walk a distance during the day of ten parasangs ** Ancient Persian measure of length about 3-1/4 miles. and more, and his path is filled with stumbling blocks, mud and stones, and there are plunderers and murderers along that way and he must go in spite of all of this, for so has the king commanded him and he is not able to avoid it, how must this man first prepare in the morning and gird his loins with alertness and walk speedily? Therefore, how important it is to rise early and to begin early the service of the Creator, may He be exalted. And even though he does all that is in his power, he will attain only a little of the needed qualities. As our Sages expounded (Aboth de R. Nathan, chap. 16) on the verse, "For he knoweth our frame" (Ps. 103:14). They told a parable of a king who gave a field to his servants and he told them to till it and guard it and to extract from it thirty kur (of produce) every year, and they busied themselves in this matter and tilled it well, but they brought before the king only five kur. He said to them, "What is this that you have done?" They said to him, "Our lord, the king, the field you gave to us has poor soil, and though we worked it with all our might it did not produce more than this amount. Thus, man, even though he works with all his strength, his accomplishment is little and if he says, "I will wait until I have time or until I earn enough for my needs," know that the troubles and responsibilities of this world never cease. As our Sages said, "And say not, 'When I have leisure I will study'; perhaps you will never have leisure" (Aboth 2:5).
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Orchot Tzadikim

It is written in the Torah, "It is not in heaven" (Deut. 30:12) and the meaning of this is : it is not to be found among those that are arrogant and consider themselves as high as heaven. "Neither is it beyond the sea" (Deut. 30:13), which means that it is not to be found among those who are constantly travelling on sea voyages (Erubin 55a). Therefore, our Sages, of blessed memory, said, "Nor can one who is engaged overmuch in business grow wise" (Aboth 2:6). And they said, "Engage less in business, but occupy yourself with the Torah" (Aboth 4:12).
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