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In order to better understand ones purpose, merits and relationship (etc.) with Hashem is there any merit in trying to figure out the מדה כנגד מדה aspects of one's life? Should one dwell on such things or is מדה כנגד מדה a device that is used in understanding events of the past? i.e. if something happens to me (for the good or bad), is there any way of being certain that I will come to a correct conclusion?

I know there is a concept of 'searching your deeds' (or חשבון הנפש) when something negative happens but is the point to come to a definite conclusion (i.e. 'this' caused 'this') or just general reflection leading to positive action?

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Related: Interpreting divine messages –  Michael Sandler Apr 3 at 7:27

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The gemara in berachos 5a discusses a person who has yesurin (suffering) and says he should investigate his actions:

...אמר רבא ואיתימא רב חסדא אם רואה אדם שיסורין באין עליו יפשפש במעשיו

...פשפש ולא מצא יתלה בביטול תורה

It says if he "doesn't find anything" he should assume it is because of bittul Torah. Rashi on "doesn't find anything" says

לא מצא עבירה בידו שבשבילה ראוין יסורין הללו לבא

"he doesn't find any sin for which this (emphasis mine) suffering should have come." The gemara indicates that the proper response to suffering is introspection into ones actions, and, evidently, one can figure out what sins he did to cause a certain suffering.

There is a famous story (famous because I have heard it) about R' Isar Zalman Meltzer that goes as follows: A man came to visit R' Meltzer. While they were talking, a noise came from the kitchen and R' Meltzer's wife cried out. He ran into the kitchen, there was some quiet discussion, and then they both left the house, leaving this man waiting. When he came back, he said "where were we" but the man asked for an explanation of what had happened. R' Meltzer told him that a pot of milk in the kitchen had boiled over and spilled. He and his wife had a discussion to figure out why such a thing would happen, and then she realized that they had not paid the milkman. They ran out to find the milkman, and when they paid him, he informed them that he had not known how he was going to buy food for dinner that night.

It doesn't always work out that smoothly, but at least R' Isar Zalman Meltzer felt it was worthwhile to try to figure it out.

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