Is it Possible to be Orthodox and Completely Miss the Point?

The Danger of Halacha - A Simple Model
Being a frum Jew requires us to know how to successfully navigate Halacha. This is a very important, nay, fundamental, aspect of Judaism because it keeps us away from aveiros. Perhaps the most basic element of observance of Torah is the ability to know what one is permitted to do versus what one is not permitted to do. This keeps us on the "straight and narrow."

While absolutely necessary, this approach nevertheless comes with a price tag and an implicit danger, and that danger is that it often leads a frum Jew to lose sight of the Torah's conceptualization of proper behavior.

The Breakdown
Let's break this down...

Every frum Jew knows that the Torah's two main classifications of mitzvos are positive (248) and negative (365). For the sake of clarity we will refer to positive mitzvos as "things that you must do," and negative mitzvos as "things that you must not do." These two classifications exist at polar opposites ends of the behavior spectrum. For example, I must wear tefillin; I must not murder.


So far, what has been said until now is basic and something that all Orthodox Jews agree on.

However, what comes next is not as clear. The distinction used when navigating Halacha is not must vs. must not, but rather can vs. cannot. If we think of these two in terms of the model above, it is relatively clear that the while the opposite of must not is must, the opposite of cannot is not can! In truth, "can" exists somewhere in between the two poles, and it has no opposite.

To make this easier to understand, we should realize that the words "must not" and "cannot" mean the same thing. When you ask your Rav a shaila and he says that you can't do something, his answer is based on that action being (or related to) an issur in the Torah. He says that you can't do it because the Torah says that you must not do it. Therefore "cannot" is the Halachic expression of a Torah prohibition and is equal to "must not."

Because the English terms may be confusing in this context using the Halachic terminology makes more sense. The opposite of issur (איִסוּר) is not heter (הֶתֵר), the opposite of issur is chiyuv (חִיוּב). For Halachic reasons it is necessary to classify things in this manner, but doing may so inadvertently lead us to lose track of the joy of observance and of the correct mindset.
This highlights the interesting realization that can is in fact a third category that falls in between must not and must; it is not the opposite of must not. In actuality, the can category is a very broad category that occupies the entire middle ground between these two polar opposites. We have become accustomed to treating can as the opposite of cannot, when it in fact refers to things that are neither mandatory nor restricted.
So What?
If we are able to keep this distinction clear in our heads then there is no problem with asking our rabbonim if we are permitted to do something. To the contrary, a person who has yiras shamayim and humility will seek out Halachic guidance.

The problem starts with our motivation when asking Halachic questions. While we may be asking our Rav what we can do from a genuine place of yiras shamayim, we may also be asking as a means to acquire Halachic permission to do something. The underlying reality of inquiring about Halachic permission may stem from a hidden desire to be liberated from obligation. The truth is that only the person asking the question knows his true motivation, although that may be debatable as well.

This does not indicate that the person asking the question is evil or seeks to cast off 'ol malchus shamayim, but instead is the fairly common tendency to lose focus of the purpose of observing commandments in the first place, which is to connect with God. The commandments become equated in his psyche with things that prevent pleasure. Regarding positive mitzvos, he looks for ways to avoid situations that obligate him. Regarding negative mitzvos, he looks for ways to get away with as much as he can without crossing the line into a transgression. He begins to operate almost completely in the "can zone" of the spectrum. He loses sight of the grand pleasure that may accompany performing mitzvos when understood in their proper context. If he is frum from birth, how does he find satisfaction in his lifestyle? If he is a ba'al teshuva, why has he become frum in the first place?

I always had a hard time understanding the following verses:

"All these curses will befall you, pursuing you and overtaking you to destroy you because you did not obey the Lord, your God, to observe His commandments and statutes which He commanded you. And they will be as a sign and a wonder, upon you and your offspring, forever, because you did not serve the Lord, your God, with happiness and with gladness of heart, when [you had an] abundance of everything." (Deuteronomy 28:45-47)

וּבָ֨אוּ עָלֶ֜יךָ כָּל־הַקְּלָל֣וֹת הָאֵ֗לֶּה וּרְדָפ֨וּךָ֙ וְהִשִּׂיג֔וּךָ עַ֖ד הִשָּֽׁמְדָ֑ךְ כִּי־לֹ֣א שָׁמַ֗עְתָּ בְּקוֹל֙ יְ-הֹוָ֣ה אֱ-לֹהֶ֔יךָ לִשְׁמֹ֛ר מִצְו‍ֹתָ֥יו וְחֻקֹּתָ֖יו אֲשֶׁ֥ר צִוָּֽךְ: וְהָי֣וּ בְךָ֔ לְא֖וֹת וּלְמוֹפֵ֑ת וּבְזַרְעֲךָ֖ עַד־עוֹלָֽם: תַּ֗חַת אֲשֶׁ֤ר לֹֽא־עָבַ֨דְתָּ֙ אֶת־יְ-הֹוָ֣ה אֱ-לֹהֶ֔יךָ בְּשִׂמְחָ֖ה וּבְט֣וּב לֵבָ֑ב מֵרֹ֖ב כֹּֽל:(דברים כח:מה-מז)

Perhaps this is what God meant.

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