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If a boy (teenager) learned he will not be punishesd until he is 20 and decides to go off the derech with the plan to do teshuvah at 20, would HaSh-m accept his teshuva?

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    Of course. Because teenagers do these sort of idiotic behaviors, that's why they are not punished by the Heavenly court to begin with until they mature. – LN6595 Feb 21 '16 at 22:50
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    Rambam points out that if someone sins with the intent to "do teshuvah" to avoid punishment, it is not a valid teshuvah That is because he does not really regret it. To truly do teshuvah he must honestly regret his action, and try to amend his deeds. – sabbahillel Feb 21 '16 at 23:48
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    @sabbahillel But if someone plans to "do teshuva later" but then seriously regrets his decision, of course he can do teshuva. – Daniel Feb 22 '16 at 1:35
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    @Daniel The point is that while he can do teshuva, it is much more difficult for him than for someone who was honestly trying to do the right thing to begin with. It is like someone who veers off the correct path. The longer he goes along the wrong path, the harder if is to correct and go back to the right path. Consider someone going along the wron radius of a circle, he has much farther to travel to get to the right point along the circumference than near the center of the circle. – sabbahillel Feb 22 '16 at 1:59
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    See judaism.stackexchange.com/a/8751/1570 . It's not so clear the assumption about the lack of judgment before age 20 is entirely corret. – Micha Berger Feb 22 '16 at 15:33
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The implication of the last mishna in Yoma is that the answer is no:

האומר, אחטא ואשוב, אחטא ואשוב, אין מספיקין בידו לעשות תשובה.

One who says, "I will sin, and then repent, I will sin, and then repent," will not receive an opportunity to repent.

This is codified by Maimonides is the Laws of Repentance 4:1:

אַרְבָעָה וְעֶשְׂרִים דְּבָרִים מְעַכְּבִין אֶת הַתְּשׁוּבָה. אַרְבָּעָה מֵהֶן עָוֹן גָּדוֹל וְהָעוֹשֶׂה אֶחָד מֵהֶן אֵין הַקָּדוֹשׁ בָּרוּךְ הוּא מַסְפִּיק בְּיָדוֹ לַעֲשׂוֹת תְּשׁוּבָה לְפִי גֹּדֶל חֶטְאוֹ. וְאֵלּוּ הֵן... ד) וְהָאוֹמֵר אֶחְטָא וְאָשׁוּב ...

Twenty-four things prevent teshuvah. Four of them are a great sin and anyone who does one of them, the Holy Blessed One does not enable that person to repent because of the seriousness of his sin, and they are: ... and (4) someone who says, “I will sin and I will repent,” ...

  • The mishnah could be understood pragmatically. Someone who develops the wrong habits will have a hard time breaking them when they do finally decide to do so. I believe that's why the Rambam shifts the language from implying that someone is denying his opportunity to do teshuvah to the act itself holding up the teshuvah -- "מְעַכְּבִין אֶת הַתְּשׁוּבָה". And only then says more literally the mishnah, although saying it's HQBH in particular who won't give him opportunity, since it's He who made people that way. The person who thinks they have until 20 – Micha Berger Feb 22 '16 at 15:37
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I would imagine the Mishna in Yoma presupposes that we are discussing an intelligent adult and therefore not an applicable halacha here...The whole premise of "the under 20 pass" is the lack of foresight and intelligence a teenager has, see this http://mariacapaz.pt/wp-content/uploads/2015/06/Pris%C3%A3o-foto-5.jpg Simply put the under 20 teen makes mistakes so the outcome of his sins and business dealings are suspended even the postponing of repentance would fall under "the under 20 pass" and not under האומר, אחטא ואשוב, אחטא ואשוב, אין מספיקין בידו לעשות תשובה.

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