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How does one decide?
Below is a wonderful Chabad teaching that sheds light on this important topic. It was produced for Chanukah however the teaching goes far beyond the holiday. The lighting of the candles, the oil, etc. is used as a metaphor for these two approaches. Both are presented as being correct and having merit.
During the first century BCE two great rabbis debated many topics about what it means to be Jewish and how halacha (Jewish law) should be applied to daily life. In general terms Rabbi Hillel advocated for a "big tent" approach that sought to include all Jews and welcome others while Rabbi Shammai favored a "small tent" approach in which only those who were genuinely observant would be included. To this degree the argument is between Judaism being a small community of tzadikim (truly righteous people) or a larger community where all of Israel is included regardless of their level of observance. Both approaches have positives and negatives.
Overall the big tent approach of Rabbi Hillel was determined to be the most applicable to the realities of Jewish strengths and weaknesses. The negative to this perspective was that the importance of holiness and observance was sometimes minimized in favor of inclusiveness.
In today's world, especially in the diaspora (i.e. Jews living outside of Israel), this approach has arguably resulted in the growth of a Judaism that has become so assimilated with the various non-Torah based cultures that the uniqueness and purpose of the Covenant has been weakened and in some cases abandoned completely. So we have the same question today.
Can one be too observant? Can one not be observant enough? What does it mean to be observant today? Must we in the 21st century conform to rules established in the pre-modern era that seemingly no longer apply? Is not Judaism a living organism that must adapt and conform with the times if it is to survive? Is it possible to go too far with this, in either direction? Where should we set our boundaries? These are the essential debates between the Orthodox and non-Orthodox movements. The more things change the more they stay the same.
Once Messiah comes Shammai's approach will certainly be the best. Then we will know the truth. Then there will be a righteous King on the Throne of David. Then the tzadikim will teach openly and then all will partake in the truth of Torah. Then the righteous Noahidim (people of the nations) will come to Jerusalem's Holy Temple and make sacrifices to HaShem knowing His Will and the role of the Jews as His anointed priesthood to the nations (Exodus 19:6). Then they will learn and make peace with the Jewish people. Then... Oy! Such a time it will be!!
Until Messiah comes however, we must not allow the perfect (Shammai) to defeat the good (Hillel). In other words, as Rebbe Nachman says, "a little is better than none" for now. So don't stress over observing the minutia of laws and traditions. Such forced pseudo holiness can actually move one away from HaShem because such a person thinks, I just can't do it! I don't know the proper rites and words, the rabbis can't even agree so how am I supposed to do this!
Don't worry! Be happy! Just keep growing, learning and gradually increasing your emuna (active faith). Your service to HaShem with the intention (kavanah) to please Him is enough. "Torah was given to fallible humans, not to the angels" as Rebbe Nachman also teaches. HaShem knows your heart. Study Torah and do what you are able to do with the understanding you currently have.
So, in this Chabad presentation the rabbi offers wonderful insights into these issues. I hope you are blessed by it.
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