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The Mesilat Yesharim (ch.4) quotes the Talmud (Bava Batra 75b) which says in Olam Haba (the World to Come) every person will be singed by the chupah (canopy) of his fellow, an analogy referring to the regret one feels for not attaining what his fellow had attained and that for those who were slack "there is no doubt, that their suffering will be enormous and everlasting".

Why is Olam Haba a reward then if everyone except for the top people (who fulfilled their full potential) are just going to suffer forever.

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    Where did you find in the chapter that if you are not "on top?" there is no doubt, that their suffering will be enormous and everlasting" ??? Look up for Mishna Sanheddin 10 for discussion about who has and who "has not" "Olam Haba". It starts with "All Jews have a share in the World to Come, as it says, (Isaiah 60:21), “Thy people are all righteous; they shall inherit the land for ever, the branch of my planting, the work of my hands, that I may be glorified.”"
    – Boris
    Nov 25, 2016 at 7:25
  • @Boris mesilat yesharim ch.4
    – ray
    Nov 25, 2016 at 7:25
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    I looked up here in first place, I can see the "hupa" allegory but I cannot see the "everlasting suffering" thing, can you quote the hebrew passage?
    – Boris
    Nov 25, 2016 at 7:28
  • ודאי שיכירוהו לאמיתו לצערם ולבשתם, ודאי שלא יהיה להם זה אלא צער גדול ונצחי. he is referring to his earlier statement ועל זה אמרו ז"ל (ב"ב עה): על דרך המשל, מלמד שכל אחד נכוה מחופתו של חבירו @Boris
    – ray
    Nov 25, 2016 at 7:29
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    Thanks. May be Rabbenu spoke in some kind of exaggeration trying to wake up the hearts for "avodat hashem". In any case, I would be cautious about judging the "world to come" in our terms in general.
    – Boris
    Nov 25, 2016 at 7:49

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While it is true that there will be an element of regret that one didn't achieve as much as he/she could have, the Mesilat Yesharim also states that there will be the great joy of closeness to God commensurate with one's achievements. These two elements are not mutually exclusive, so it is not true that everyone is "just going to suffer forever". The question projects human cognitive distortions onto souls in the afterlife, namely that if there is some negative aspect or pain then that overshadows all the positive which is then discounted and not enjoyed. In truth it is possible to experience great joy which is also tinged with sadness.

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