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I recall a high-school rebbe (teacher) of mine quoting a great rabbi as having said that, if someone religious becomes irreligious, then God will punish him for every time he does not wash his hands before eating bread.

I recently read the first chapter of The Thinking Jewish Teenager's Guide to Life. It's devoted to the idea that everyone always has a spiritual level, and that any seeming challenge not at that level is not considered a challenge for him — it is either something he will certainly do right or something he will certainly do wrong, even if merely out of habit — so he gets no reward or punishment for it.

I don't see that these two views can be reconciled. Most likely someone who loses his religion will not be at a level such that washing his hands before eating bread will be his challenge.

Are these two opposing views held by different philosophical rabbis or schools? What rabbis or schools? Or can they be reconciled? How?

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This idea that "everyone always has a spiritual level, and that any seeming challenge not at that level is not considered a challenge for him — it is either something he will certainly do right or something he will certainly do wrong, even if merely out of habit — so he gets no reward or punishment for it" is probably being quoted out of Michtav me'Eliyahu by Rav Eliyahu E. Dessler. If I remember correctly, Rav Dessler says that someone who took action to raise or lower his spiritual level (thereby changing some behavior from free will to habit) is punished or rewarded each time he does the action for having made the change to his spiritual level.

More concretely, if someone was not shomer Shabbat, and raises his spiritual level to the point where he wouldn't even entertain the notion of breaking Shabbat, then according to Rav Dessler, Shabbat is not something he has free will over anymore. In such a situation, each time the person keeps Shabbat, he is rewarded for having raised his spiritual level to the point where keeping Shabbat is a given.

When is a person not rewarded for keeping Shabbat? Rav Dessler says that he's not rewarded when he was raised keeping Shabbat, and keeping Shabbat was always a given in his life, and there was never a time when he would entertain not keeping Shabbat. (If this sounds implausible, read his essay in Michtav me'Eliyahu or Strive for Truth, because a scriptural example of this situation is actually his point of departure for introducing the entire idea that I've described here.)

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Do you or anyone else have a more specific source, e.g chapter, section, etc.? –  Menachem Oct 13 '13 at 20:02
    
See aishdas.org/ta/5765/bo.pdf "Rabbi Eliyahu Dessler, z"l (Michtav Me'Eliyahu I, pg 113), describes the concept of "nekudas habechirah" (lit. "the point of free will")." –  Avrohom Yitzchok Jan 19 at 21:25
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