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In this lecture by Rabbi Ammon Yitzchak, he mentioned a story about the Chofetz Chaim, around timestamp 26:45, that a person requested to be in the Olam Haba of the Chofetz Chaim or to be in the midst of the Chofetz Chaim in Olam Haba.

My questions are:

Which statement is more accurate? That we will be in the midst of others in the Olam Haba, or that each person has their own Olam Haba?

And: Can, and if yes how, one assure Olam Haba for another person?

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    Your link to "this question" seems wrong
    – Rabbi Kaii
    Aug 3 at 13:35
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    @RabbiKaii I edited it to correctly portray my questions, this was a draft I had and didn’t notice, Thanks!
    – Jewish Context
    Aug 3 at 16:20

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We will be in the midst of others in Olam Haba.

יקבצו הטובים ויעשה מהם כלל א' שלכלל ההוא יעותד העה״ב בטוב האמיתי המושג בו

The good ones will be gathered and made into a group. For the true good that is attained in Olam Haba is destined for this group...

'שתכלית כל הענין הוא לקבץ קיבוץ שלמים שיהיו ראוים ליקבע לנצח בהתדבקותו ית

...The purpose of the whole matter is to gather together a group of Perfected Ones who will be fit to be established in an eternal state of intimacy with Hashem.

Derech Hashem 2:2. Derech Hashem 1 and 2 both cover this in much more detail, although of course there are many secrets involved.

How can a person ensure Olam Haba for another? I'm not sure about ensure, there's only so much the Tzaddikim can do, but we do daven every day that we should merit to attach to them in Olam Haba by saying וְשִׂים חֶלְקֵֽנוּ עִמָּהֶם, and place our lot with theirs.

The secrets of this are beyond our comprehension. However, a small drop has been revealed to us by the Ari Hakodesh T'zl through his student R' Chaim Vital T'zl, in Shaar Hagilgulim, and the souls of the less worthy are able to become attached to the souls of the wholly righteous, thus attaining eternal life through them. Building off the pasuk in Shmuel 2:14:14:

לֹא יֵאָסֵפוּ וְלֹא־יִשָּׂא אֱלֹהִים נֶפֶשׁ וְחָשַׁב מַחֲשָׁבוֹת לְבִלְתִּי יִדַּח מִמֶּנּוּ נִדָּח

God does not take away life, rather He devises strategies in order that the banished ones should not be banished.

This is very complex and there is a lot of nuance, but even those who are unable to bring a tikkun to even one limb of their soul are still not completely cut off, but have their good distributed among the souls of others (see 4:6).

See also Sha'arei Ramchal, chapter 106 (thanks to fulltimekollelguy for the image).

Shaar Hagilgulim also gives us a general impression towards the title question, that we will, to whatever extent possible, placed with souls similar to us, and that means we are more likely to be with friends and family than not, although again these are very secret matters, and it is clear our merit plays a big role in this. How this looks in practice is going to have to be a surprise!

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    great answer, thank you. So does this mean there are multiple destinations in Olam Haba?
    – Jewish Context
    Aug 3 at 16:25
  • @JewishContext thank you. וכבר ימצאו בקיבוץ ההוא עליונים ותחתונים גדולים וקטנים - "Within this group there will exist higher ones and lower ones, greater ones and smaller ones"...שאלו היה הדין נותן עליהם שיוגמלו בעה״ב ולא בעה״ז כבר היו נמצאים האנשים ההם במדריגה מן הגבוהות בקיבוץ השלימים: - "If not for the fact that they had to have their compensation in this world, these [less meritorious ones] would have been found at the level of the highest order of Perfected Ones". Not sure about different destinations but certainly different levels. Learn Derech Hashem 1 & 2, it shouldn't take a few hours
    – Rabbi Kaii
    Aug 3 at 17:30
  • "How can a person ensure Olam Haba for another? I'm not sure about ensure, there's only so much the Tzaddikim can do..." I take it you never heard about the non -religious, Jewish man in Brooklyn who saw himself in the Heavenly Court while under anesthesia fro a serious surgery. He received a judgement of execution and then a particular person entered the courtroom. All present, stood in honor of his arrival. That individual took personal responsibility for the one judged & he was released under his custody. The individual survived his surgery and searched to find the man who had saved him.
    – Yaacov Deane
    Aug 3 at 18:40
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    He was told that in his particular case, that mitzvah was the mitzvah of mezuzah. His assurance for Olam HaBa was that one commandment. A wild story with many implications to reflect upon over fabrengen.
    – Yaacov Deane
    Aug 7 at 3:57
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    @YaacovDeane this reminds me of a video that was doing the rounds about 15-18 years ago of a man in Israel who died on the hospital bed and had a very intense experience of being judged etc. Got given a second chance, woke up remembering it, immediately became shomer mitzvot and a lamdan, and sobs intensely whenever he recounts the story. I wish I could find it.
    – Rabbi Kaii
    Aug 7 at 9:34

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