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Over the last couple of weeks, I had a question that has been bothering me about Succos.  I have found that on the one hand the Succah has the status of Chutz La’eretz (any place outside the Land of Israel), whereas on the other hand the Succah has the status of Eretz Yisrael (Israel).
There are sources that support both notions.  For instance, in the Yehi Ratzon prayer said upon entering the Succah it says, “And in the merit of my leaving my house to go out, may this be reckoned for me as if I have wandered afar.”
This means to say that if a harsh decree of exile has been sentenced upon us over the High Holidays, then we ask God to consider our going out of our homes into the Succah as some sort of fulfillment of that decree.  In this way, we will not have to leave our homes in a more permanent way.
According to this liturgical passage, going into a Succah is like going into exile.  Exile, by definition, means going to Chutz La’aretz.  So it comes out that our Succahs have the status of Chutz La’aretz.
On the other hand, the Vilna Gaon compares the Succah to Eretz Yisrael since both Mitzvos are fulfilled with not just one or two limbs but with our entire body. (See Kol Hatur, chap. 1, Para. 7)
According to the Gr”a, going into a Succah is like going into Eretz Yisrael.  Herein lays the apparent contradiction regarding the status of the Succah.  Is it likened to Chutz La’aretz or to Eretz Yisrael?  Will the real Succah please stand up?
I have not yet found commentaries that address this question directly.  However, I did come across some ideas found in various sources that I would like to borrow from, modify, and adapt, in order to offer one approach in answering this difficulty.
The Talmud shares a Tannaic debate as to what our Succos represent.  According to Rebbi Akiva, our Succos commemorate the actual booths that our ancestors built and dwelt in during their forty years of wandering through the desert.  However, according to Rebbi Eliezer, our Succos symbolically represent the Clouds of Glory that protected our ancestors throughout they journey in the desert (Tractate Succah, chap. 1,”Succah Shehi Gavoah”, pg. 11a).
The Piskei Teshuvos (Rabbi Simcha Rabinowitz, Hilchos Succah, 625:1, footnote 3, based on the Chassam Sofer (Drashos, Drash 53) applies the rule of thumb , “These and those are the words of the Living God” (Eiruvin, chap. 1, “Mavoi Shehi Gavoah”,pg. 13b) to this debate between Rabbi Akiva and Rabbi Eliezer.
He explains that in the desert there were two categories of Jews.  There were Jews on a higher spiritual level, and then there were Jews on a lower spiritual level.  The Jews that were on a higher spiritual level were protected by the Clouds of Glory (like the opinion of Rebbi Eliezer).  However, the Jews that were on a lower spiritual level were spat out from Clouds of Glory.  What did those Jews do in order to protect themselves from the oppressive desert sun?  They built booths for themselves (like the opinion of Rebbi Akiva).
Along these lines, we could suggest the same methodology to answer our question above.  For Jews on a lower spiritual level, who received a harsh decree of exile over the High Holidays, their Succahs are likened to Chutz La’aretz.  However, for Jews on a higher spiritual level, who never had the harsh decree of exile sentenced on them, their Succahs are on the status of Eretz Yisrael.
This is why the holiday is called “Chag HaSuccos” in the plural, as opposed to “Chag HaSuccah” in the singular.  The very name of the holiday teaches us that there are two types of Succos that the Jewish people will be celebrating in.  For some Jews the Succah will be the highest, Eretz Yisrael, while for other Jews the Succah will only be on the lower level of Chutz La’aretz.  The constitution of our Succos depends on our spiritual status.
One of the primary aspects that determine what spiritual status our Succahs have is our thoughts and intent.  For example, you can have a Jew who lives in Israel and yet pines to be in a different country.  All he dreams about are the materialistic advantages to be gained in that country.  Spiritually speaking, such a Jew is considered to be living in Chutz La’aretz.
This is because of a teaching from the Ba’al Shem Tov that says that a person is really where their thoughts are turned to.
Similarly, you can have a Jew who lives in the Diaspora and yet longs to be in Eretz Yisrael.  It’s just that there are circumstances out of his control that prevent him from making Aliyah, like illness for example.  Spiritually speaking, such a Jew is considered to be living in Eretz Yisrael.  It all depends on what our values are and what we wish for.
For the Jews whose minds are focused on Eretz Yisrael and what it represents, namely, Kedushah (holiness) and Tahara (purity), their Succahs become the embodiment of Eretz Yisrael.  However, for the Jews whose thoughts are constantly on Chutz La’aretz and what it represents, namely, the pursuit of material gain, their Succahs take on the essence of Chutz La’aretz.
In order for us to benefit from the spiritual advantages of an Eretz Yisrael type Succah, we could suggest to make a wish list.  Write down the things we want most in life.  What are our goals?  Read the list back to yourself to see if the desires are leaning more towards the spiritual or the physical.  Then we can determine where we are and where we would like to be.
If we would like to become the person who dreams more about the needs of the soul than the needs of the body, we can start to study about creation, the world, its purpose, the Mitzvos, etc…in order to deepen our appreciation for that which is eternal.
So, may we all be blessed with a healthy value system, yearning, longing, and pining for spirituality, so that our Succos take on the essence of Eretz Yisrael, and thus merit to have the Seven Shepherds of Israel be our guests in our Succos, culminating with another guest, the Moshiach, who will build the Succas Dovid Hanofales (The Succah of David, (The Temple), that has fallen).
Good Yom Tov,
Good Shabbos,
A Good Moed,
Warmest wishes,
Aba Wagensberg

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Rabbi Aba Wagensberg, a close Talmid of Harav HaGaon Rav Chaim Pinchas Sheinberg, ZT”L, is a sought-after lecturer in institutions in Israel and abroad. Rabbi Wagensberg is the author of "Inspiring Change" (about self growth) and "A Shot of Torah" (a collection of shorter divrei Torah on the Parsha and holidays), as well as weekly Torah articles. He has created a Torah audio and video library and can also be heard weekly on the Lakewood radio station, Kol Berama 107.9 FM.