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Should someone take on a new stringency/hiddur/optional mitzvah if he or she is not absolutely sure he and his progeny will be able to maintain it on all further occasions? In such a case, is it better to take the risk and rely on G-d's future help in order to grow one's avodah, or not to take such a risk at all?

(It would seem that taking on a new practice by a "bli neder" is the best possible option. However, it's still unclear to me how often one has to say/think "bli neder" in order to retain that status. Is it by every performance of the mitzvah? One in three? When one starts? And if there is a risk of messing up the "bli neder," should one not undertake the mitzvah?)

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    Offhand, no. There is an expression / Al thei tzaddik harbeh - loosely translated as "Don't be overly righteous". Generally, one is not required to be machmir. (Yes, I know that there are numerous mitzvot where Shulchan Aruch recommends to do so. Those are usually situations where there is doubt regarding which ruling to follow.) Otherwise, if one is machmir when he is not sure he can do it, what is his purpose of dong so, when he doesn't need to? Is he "showing off"? – DanF May 29 '17 at 1:08
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    Maybe you should ask the parenthetical question as the main question and save the other part for after you get an answer to that – Double AA May 29 '17 at 1:11
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    @SAH short answer--- It is not advisable. But, if one is sincere and pretty much certain they can handle it, and they really feel it will be a good thing in serving Hashem for various reasons...then one bli-neder at the start is fine. That way they can stop later if needed. Never "take anything on" is the usual rule. This is my opinion based on, my Rebbeim, my Torah learning, and life experience.(Experience is a kind of knowledge you get two minutes after you really needed it. :) ) – David Kenner May 29 '17 at 2:28
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    Numerous reasons - many valid, many not. Many are machmir because they don't know that there's an easier option. They haven't thought through the nuances and just followed what someone told them to do. Others have thought through it, and, do want to increase their observance level. But, they understand why they do it, know the choices and have made a conscious choice to be machmir, expecting to succeed, and most of them do. You're asking if somene should begin being machmir while being nervous that he may fail. That's my main point of question to you and anyone who tries that. Why? – DanF May 29 '17 at 2:32
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    "he or she is not absolutely sure he will be able to maintain it on all further occasions": isn't that always the case? – msh210 May 29 '17 at 4:33

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