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It says in Tehillim 90 (a chapter attributed to Moshe Rabbeinu, if that affects anything):

יא: מִֽי־י֖וֹדֵעַ עֹ֥ז אַפֶּ֑ךָ וּ֜כְיִרְאָֽתְךָ֗ עֶבְרָתֶֽךָ: לִמְנ֣וֹת יָ֖מֵינוּ כֵּ֥ן הוֹדַ֑ע וְ֜נָבִ֗א לְבַ֣ב חָכְמָֽה: 11 Who knows the might of Your wrath, and according to Your fear is Your anger. 12 So teach the number of our days, so that we shall acquire a heart of wisdom.

I saw in another translation: "According to the fear of You is Your anger."

I was trying to find out what all this means and saw the following gemara (Taanit 8a or thereabout) :

אמר רבי יוחנן כל המצדיק את עצמו מלמטה

מצדיקין עליו הדין מלמעלה שנאמר אמת מארץ תצמח וצדק משמים נשקף רבי חייא בר אבין אמר רב הונא מהכא (תהלים צ, יא) וכיראתך עברתך

§ Rabbi Yoḥanan said: Whoever is exacting with himself, by striving to act righteously in every way on earth below, he is judged in an exact manner in Heaven above, in order to improve him further still, as it is stated: “Truth springs out of the earth, and righteousness has looked down from heaven” (Psalms 85:12). Rabbi Ḥiyya bar Avin said that Rav Huna said that this idea is derived from here: “And Your wrath is according to the fear that is due to You” (Psalms 90:11). The level of God’s wrath correlates with the offender’s fear of God.

ריש לקיש אמר מהכא (ישעיהו סד, ד) פגעת את שש ועושה צדק בדרכיך יזכרוך הן אתה קצפת ונחטא בהם עולם ונושע אמר ריב"ל כל השמח ביסורין שבאין עליו מביא ישועה לעולם שנאמר בהם עולם ונושע

Reish Lakish said that this principle is derived from here: “You took him away who joyfully performed righteousness, those who remembered You in Your ways, behold You were wroth, and we sinned, upon them have we stayed of old, that we might be saved” (Isaiah 64:4). This verse also teaches that God displays wrath specifically due to the transgressions of those who are accustomed to acting righteously.

This is all very difficult to swallow. It seems to say that one who sins only occasionally is punished more harshly for his sins than one who sins frequently. How does it not fly in the face of the entire reward and punishment doctrine? (Is it suggesting, for example, that one is still rewarded for increasing observance, but with diminishing returns?)

We have a mitzvah to fear G-d at all times, said Rambam or maybe Rashi. But the assertion that "the level of God’s wrath correlates with the offender’s fear of God" is hardly encouraging in this matter. (How can we give our utmost in this mitzvah anyway?)

Finally, how does this all square up with the known idea (again I can't find the source, but I am quite sure it exists in Chasidus Chabad if not elsewhere--I think it is the primary thought underlying the over-the-top efforts we make for Pesach, for example) that one endeavors to go beyond the letter of the Law precisely out of love and gratefulness to G-d for His own chesed in dealing with us? It seems quite backwards that we should set ourselves up to incur punishment if G-d forbid we fell short of our ambitions.

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There are several Talmudic passages that can hopefully provide us with some context to understand this:

Yevamot 121b

אמר רבי אבא אע"פ כן מת בנו בצמא שנאמר וסביביו נשערה מאד מלמד שהקדוש ברוך הוא מדקדק עם סביביו כחוט השערה ר' חנינא אמר מהכא אל נערץ בסוד קדושים רבה ונורא על כל סביביו

R. Abba stated: His son nevertheless died of thirst; for it is said in Scripture, And round about Him it stormeth mightily, which teaches that the Holy One, blessed be He, deals strictly with those round about Him even to a hair's breadth. R. Hanina said, [Proof may be adduced] from here: A God dreaded in the great council of the holy ones, and feared of all them that are round about Him. (Soncino translation)

As explained by Rashi there:

שכך דרכו של מקום לדקדק עם החסידים

For so it is the way of the Omnipresent to be strict with the pious.

Eruvin 22a

ומשלם לשונאיו אל פניו להאבידו א"ר יהושע בן לוי אילמלא מקרא כתוב אי אפשר לאומרו כביכול כאדם שנושא משוי על פניו ומבקש להשליכו ממנו לא יאחר לשונאו א"ר אילא לשונאיו הוא דלא יאחר אבל יאחר לצדיקים גמורים והיינו דא"ר יהושע בן לוי מאי דכתיב אשר אנכי מצוך היום לעשותם היום לעשותם ולא למחר לעשותם היום לעשותם למחר לקבל שכרם א"ר חגי ואיתימא ר' שמואל בר נחמני מאי דכתיב ארך אפים ארך אף מבעי ליה אלא ארך אפים לצדיקים ארך אפים לרשעים

And repayeth them that hate Him to His face, to destroy him. R. Joshua b. Levi remarked: Were it not for the written text one could not possibly have said it. Like a man, as it were, who carries a burden on his face and wants to throw it off. He will not be slack to him that hateth Him. R. Il'a explained: He will not be slack to those that hate Him, but He will be slack to those who are just in all respects; and this is in line with that which R. Joshua b. Levi stated: What [is the implication of] what was written: Which I command thee this day to do them? ‘This day [you are] to do them’ but you cannot postpone doing them for tomorrow; ‘this day [you are in a position] to do them’ and tomorrow [is reserved] for receiving reward for [doing] them.

R. Haggai (or as some say: R. Samuel b. Nahmani) stated: What [was the purpose] when Scripture wrote: Long-suffering [in the dual form] where the singular might well have been used? But [this is the purport:] Long-suffering towards the righteous and long-suffering also towards the wicked. (Soncino translation)

As explained by Rashi and Tosafot, this means that God saves the punishment of the wicked and the reward of the righteous for the next world – and the implication is that the righteous receive their (whatever minute amount of) punishment and the wicked receive their (whatever minute amount of) reward in this world.

Berachot 7a

אמר רבא ואיתימא רב חסדא אם רואה אדם שיסורין באין עליו יפשפש במעשיו שנא' נחפשה דרכינו ונחקורה ונשובה עד ה' פשפש ולא מצא יתלה בבטול תורה שנאמר אשרי הגבר אשר תיסרנו יה ומתורתך תלמדנו ואם תלה ולא מצא בידוע שיסורין של אהבה הם שנאמר כי את אשר יאהב ה' יוכיח. אמר רבא אמר רב סחורה אמר רב הונא כל שהקב"ה חפץ בו מדכאו ביסורין שנאמר וה' חפץ דכאו החלי יכול אפילו לא קבלם מאהבה תלמוד לומר אם תשים אשם נפשו מה אשם לדעת אף יסורין לדעת ואם קבלם מה שכרו יראה זרע יאריך ימים ולא עוד אלא שתלמודו מתקיים בידו שנא' וחפץ ה' בידו יצלח

Raba (some say, R. Hisda) says: If a man sees that painful sufferings visit him, let him examine his conduct. For it is said: Let us search and try our ways, and return unto the Lord. If he examines and finds nothing [objectionable], let him attribute it to the neglect of the study of the Torah. For it is said: Happy is the man whom Thou chastenest, O Lord, and teachest out of Thy law. If he did attribute it [thus], and still did not find [this to be the cause], let him be sure that these are chastenings of love. For it is said: For whom the Lord loveth He correcteth.

Raba, in the name of R. Sahorah, in the name of R. Huna, says: If the Holy One, blessed be He, is pleased with a man, he crushes him with painful sufferings. For it is said: And the Lord was pleased with [him, hence] he crushed him by disease. Now, you might think that this is so even if he did not accept them with love. Therefore it is said: To see if his soul would offer itself in restitution. Even as the trespass-offering must be brought by consent, so also the sufferings must be endured with consent. And if he did accept them, what is his reward? He will see his seed, prolong his days. And more than that, his knowledge [of the Torah] will endure with him. For it is said: The purpose of the Lord will prosper in his hand. (Soncino translation)

As Rashi explains:

הקב"ה מייסרו בעוה"ז בלא שום עון כדי להרבות שכרו בעולם הבא יותר מכדי זכיותיו

The Holy-One-lessed-Be-He torments him in this world without any sin, in order to increase his reward in the world to come more than his merits.

And of course there is the classic passage dealing with the general question of why the righteous suffer (and the wicked prosper):

Berachot 7a

וא"ר יוחנן משום ר' יוסי שלשה דברים בקש משה מלפני הקב"ה ונתן לו בקש שתשרה שכינה על ישראל ונתן לו שנאמר הלוא בלכתך עמנו בקש שלא תשרה שכינה על עובדי כוכבים ונתן לו שנאמר ונפלינו אני ועמך בקש להודיעו דרכיו של הקב"ה ונתן לו שנא' הודיעני נא את דרכיך אמר לפניו רבש"ע מפני מה יש צדיק וטוב לו ויש צדיק ורע לו יש רשע וטוב לו ויש רשע ורע לו אמר לו משה צדיק וטוב לו צדיק בן צדיק צדיק ורע לו צדיק בן רשע רשע וטוב לו רשע בן צדיק רשע ורע לו רשע בן רשע: אמר מר צדיק וטוב לו צדיק בן צדיק צדיק ורע לו צדיק בן רשע איני והא כתיב פקד עון אבות על בנים וכתיב ובנים לא יומתו על אבות ורמינן קראי אהדדי ומשנינן לא קשיא הא כשאוחזין מעשה אבותיהם בידיהם הא כשאין אוחזין מעשה אבותיהם בידיהם אלא הכי קא"ל צדיק וטוב לו צדיק גמור צדיק ורע לו צדיק שאינו גמור רשע וטוב לו רשע שאינו גמור רשע ורע לו רשע גמור ופליגא דר' מאיר דא"ר מאיר שתים נתנו לו ואחת לא נתנו לו שנא' וחנתי את אשר אחון אע"פ שאינו הגון ורחמתי את אשר ארחם אע"פ שאינו הגון

R. Johanan further said in the name of R. Jose: Three things did Moses ask of the Holy One, blessed be He, and they were granted to him. He asked that the Divine Presence should rest upon Israel, and it was granted to him. For it is said: Is it not in that Thou goest with us [so that we are distinguished, I and Thy people, from all the people that are upon the face of the earth]. He asked that the Divine Presence should not rest upon the idolaters, and it was granted to him. For it is said: ‘So that we are distinguished, I and Thy people’. He asked that He should show him the ways of the Holy One, blessed be He, and it was granted to him. For it is said: Show me now Thy ways. Moses said before Him: Lord of the Universe, why is it that some righteous men prosper and others are in adversity, some wicked men prosper and others are in adversity? He replied to him: Moses, the righteous man who prospers is the righteous man the son of a righteous man; the righteous man who is in adversity is a righteous man the son of a wicked man. The wicked man who prospers is a wicked man son of a righteous man; the wicked man who is in adversity is a wicked man son of a wicked man.

The Master said above: ‘The righteous man who prospers is a righteous man son of a righteous man; the righteous man who is in adversity is a righteous man son of a wicked man’. But this is not so! For, lo, one verse says: Visiting the iniquity of the fathers upon the children, and another verse says: Neither shall the children be put to death for the fathers. And a contradiction was pointed out between these two verses, and the answer was given that there is no contradiction. The one verse deals with children who continue in the same course as their fathers, and the other verse with children who do not continue in the course of their fathers! — [You must] therefore [say that] the Lord said thus to Moses: A righteous man who prospers is a perfectly righteous man; the righteous man who is in adversity is not a perfectly righteous man. The wicked man who prospers is not a perfectly wicked man; the wicked man who is in adversity is a perfectly wicked man. Now this [saying of R. Johanan] is in opposition to the saying of R. Meir. For R. Meir said: only two [requests] were granted to him, and one was not granted to him. For it is said: And I will be gracious to whom I will be gracious, although he may not deserve it, And I will show mercy on whom I will show mercy, although he may not deserve it. (Soncino translation)

In short, to whatever extent we can understand the workings of God, the seemingly harsh punishments meted out to the righteous are for good reason.

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    This is a fascinating answer; thank you. I am still waiting for insights on this topic that would explain why a non-tzaddik should still want to be righteous despite the "fact" (??) that it will get him punished here on earth. (It is very hard to hold out for the rewards of the Next World, or entirely to subjugate one's self-interest to the Will of the Creator -- though of course that is the goal.) – SAH Aug 16 '18 at 22:36
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    I don't have a source for this but basically texts dealing with this suggest that the closer you draw to Him the greater the reward for your mitzvot (in this world for some, Olam Haba for others, depends on the mitzvah) but also the greater the punishment for your transgressions. – Josh K Aug 17 '18 at 6:03

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