Pirkei Avot - Ethics of the Fathers

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Chapter 2 Mishna 16
פרק ב משנה טז

Rabbi Shimon said: Be careful with the reading of Shema and the prayer. And when you pray, do not make your prayers fixed but rather as [a plea for] mercy and a supplication before G-d, as the verse states, 'For gracious and merciful is He, slow to anger, abounding in kindness, and relenting of the evil [decree]' (Joel 2:13). And do not be wicked before yourself.
רַבִּי שִׁמְעוֹן אוֹמֵר, הֱוֵי זָהִיר בִּקְרִיאַת שְׁמַע וּבַתְּפִלָּה. וּכְשֶׁאַתָּה מִתְפַּלֵּל, אַל תַּעַשׂ תְּפִלָּתְךָ קֶבַע, אֶלָּא רַחֲמִים וְתַחֲנוּנִים לִפְנֵי הַמָּקוֹם בָּרוּךְ הוּא, שֶׁנֶּאֱמַר (יואל ב) כִּי חַנּוּן וְרַחוּם הוּא אֶרֶךְ אַפַּיִם וְרַב חֶסֶד וְנִחָם עַל הָרָעָה. וְאַל תְּהִי רָשָׁע בִּפְנֵי עַצְמְךָ


~Level 1~
Bartenura - "be careful with the Shema and prayer" - to read it in its proper time. Likewise for prayer, to pray each prayer in its proper time.
~Level 4~
Rabbi Avraham Azoulai - Ahava b'Taanugim - he used the term zehirut (be careful) because in the morning, at the time of Shema and prayer, laziness strengthens over a man to not get up from his sleep. Thus he said "be careful" to push off the laziness from yourself and get up from your sleep..
~Level 1~
Chida - Kisei David, drosh 18 - among the very first halachot in the shulchan arush is "Strengthen yourself like a lion to get up in the morning to serve your Creator..". Namely, fear of G-d at the beginning of the day, to get up in the morning and not miss the reciting of the Shemah in its time.. For if he begins by transgressing the first halacha in the Shulchan Aruch, he will go out from one evil to another, to miss prayer in a minyan, kadish, barchu, kedusha.. I don't want to say the severity of the matter so that people will not be mezid (more guilty)..
~Level 2~
Tiferet Yisrael - "be careful with the Shema and prayer" - the intent is not just that one recites the shema and prays or that one does not transgress the times. For this a complete obligation (chiyuv gamur) and our sages are speaking only of chasidut (beyond minimum obligation) (as written in Bava Kama 30a). Rather since they are a complete obligation and a man says them several times a day, therefore it is common for one to not have good intent in them. Therefore, the Tanna exhorted here that one should be careful to have intent very much.

"reading the Shema" - because one reviews to himself all the fundamentals (ikarim) of our holy faith. In the first parsha, emunah in the yichud Hash-em, blessed be He, (faith in the absolute Unity of G-d, i.e. that G-d and only G-d is absolutely One as explained in Duties of the Heart, Gate 1), love of Him, fear of Him, and torah study. Namely, one's obligations towards G-d.

The second parsha contains emunah (faith) in the divinity of the torah and guarding the mitzvot, as it opens: "And it will be if you hearken.. which I command". It also contains emunah in providence of reward and punishment in this world and also hints on reward and punishment in the next world, as it ends "in order that you lengthen your days like the days of heaven and earth". And this is only possible in Olam Haba. That is to say, do My mitzvot only for that, not for this world.

The third parsha exhorts greatly not to be swayed by the enticements of the yetzer hara (evil inclination), by lusts or heretical thoughts, as written: "do not stray after your hearts", namely, the yetzer hara, "and after your eyes", namely, bad thoughts (machshavot to'ot). For all sins of this world stem from these two.

Since all the things in these parshas are fundamentals (ikarim) to all Jews and their obligations in this world, the Holy One, blessed be He, commanded us to review them every day. Thus if despite all this, a man says them without intent (kavana), then all his recital (of the Shema) was for nothing.

Likewise for prayer, besides that in all of them one is speaking to the King, as written "blessed are You..etc.", and how could one be so brazen-faced then as to not have his mouth and heart equal, but even without this, how could he think G-d will accept his prayer if he did not plead before G-d with great humility (hachna'ah yetera). Instead of this, his thoughts fly to all corners of foolishness and vanity. Perhaps even on matters of sin. How could he not be embarrassed to say at the end of his prayer before the Knower of thoughts: "May the words of my mouth and the meditations of my heart be acceptable to You..".

What will he say if G-d answers him angrily: "what did you think in your mind?"

Therefore, our sages said: "a person's prayer is no heard unless he puts his soul in his palm", "his soul" refers to his thoughts, "in his hand" refers to watching over them well so they don't sway and so he does not forget before Whom he is standing, as written: "Let us lift up our hearts to our hands, to G-d in heaven" (Eicha 3:41).

"as [a plea for] mercy and a supplication before G-d" - to pray in a pleading manner, like a poor man standing broken hearted at the entrance to the king (Berachot 29).

"For gracious and merciful is He, slow to anger, abounding in kindness, and relenting of the evil" - there are three types of prayer and all are included in this verse:
1. that G-d saves him from troubles, and even if he sinned and "when the ox is fallen, sharpen the knife" (Shab.32a), nevertheless, that G-d will hold back anger and not punish him perhaps he will repent.

2. that G-d benefits him with some good despite that he does not deserve it according to his deeds, i.e. that G-d increases His kindness to him.

3. When he repents, that G-d forgives his sins completely and witholds the evil he deserved.

All three types of prayer are accepted only through G-d's being gracious and merciful to you. Namely, when you pray in the way of supplications (tachanunim).
~Level 1~
Bartenura - "do not make your prayers fixed" - like a man who has a fixed debt and says: "when will I unload this debt on myself?" Alternatively, "fixed", like a man who is used to reading one chapter or one parsha. He reads it rotely, not in a supplicating manner like one who seeks mercy.
~Level 1~
Bartenura - "for gracious and merciful is He" - He wants supplications and through the supplications, He immediately has mercy.
~Level 1~
Bartenura - "do not be wicked before yourself" - do not do something which today or tomorrow you will call yourself wicked due to this. Alternatively, the Rambam explained - do not be wicked in your eyes, i.e. do not consider yourself a wicked person. For due to this, you will go off to evil ways completely..