A Difficult Road Leading to a Peaceful One | Various Rabbis | Beit Midrash

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Gemara: Rabbi Avin the Levi said: One who takes leave of his friend should not say to him: "Go in peace," but should say to him, "Go to peace." This is learned from the fact that Yitro said to Moshe "go to peace" and he succeeded, whereas David said to Avsholom "go in peace," and he went and was hung. And Rabbi Avin the Levi said: One who takes leave of the deceased should not say "go to peace" but rather "go in peace," as the pasuk says "You will go to your fathers in peace" (Bereishit 15:15).

Ein Ayah: Life is full of battles. Someone who gives his friend the perception that the path of life is straight and does not alert him to the spiritual and physical pitfalls and obstacles deprives him of the power of being "armed for battle" against these challenges so that he can reach his desired goal. That is the point of the proper blessing one should give when taking leave of his friend: "go to peace." This blessing hints at the fact that the peace and completeness we strive for is always at a distance; we have not arrived at it yet. We remind our friend that there are many things fighting him, and therefore he should strive to remove these obstacles. He should realize that the path itself is not paved with peace, so that one can wish him that he will be going in peace. Rather, the path is full of obstacles that are the opposite of peace. When he makes efforts to overcome all of them, he will arrive at peace.
These difficulties of life are very different for one who has completed life and is at the point where his spirit rests. No one is fighting him or disturbing his ability to rest. The goal of the ascent that one climbs during life is that when he reaches the mountain of Hashem to enjoy the light of the King of Life, the physical battles that have to do with man’s inclinations toward the materialism will no longer be relevant. At that point, we bless the deceased person that he should go straight to his eternal rest "in peace." In other words, after death, even the path is full of peace, not just the destination. It is possible to go from one level to an even higher level. However, along the way there will be nothing that is meant to be an obstacle, which needs to be overcome or may impede the peace.
Specifically, we have two polar descriptions of parts of life: life involves toil; death involves rest. The description of life as being full of toil along with the need for strengthening is intended to bring one to increase his diligence. The description of death as restful is intended to lessen the fear of death and calm the spirit. It also encourages one to work and be active during the time that is set aside for activity, during the years Hashem granted him to do so, in order to increase the good and the peace.

Ein Ayah