A speaker once started off a seminar by holding up a $100 bill. "Who would like this $100 bill?", he asked.
Every hand in the room went up.
The speaker looked around, and then crumpled up the bill in his hand.
"Who wants it now?” he asked.
Every hand in the room stayed up.
"Well," he replied, "What if I do this?" He then dropped the bill on the ground and proceeded to stomp on it with his shoe.
He picked it up the now crumpled and dirty bill and showed it to the crowd.
"Who still wants this?"
Every hand was still up in the air.
"My friends, you have just experienced a very powerful lesson. No matter what I do to this money, no matter how crumpled or muddy it gets, it does not decrease in value. Many times in our lives, life crumples us up and grinds us in the dirt. We make bad decisions, or deal with poor circumstances, and we begin to feel worthless. We feel that Hashem has abandoned us, that He no longer values us. But no matter what has happened, and no matter what will happen, you will never lose your value. You were created b'tzelem Elokim, and nothing can change that.
Yom Kippur, the Day of Atonement, is unquestionably one of the most important days of the year. And yet, in many ways, it is a mystery. While one might assumedly categorize it as a day of suffering and sadness, Chazal refer to Yom Kippur as a spiritually uplifting day of atonement and rebirth.T here is even an element of the day that is associated with the happiness of Purim (Yom “Ki”-Purim, a day like Purim). At the same time, though, it is a fast day. We normally characterize fast days as times of mourning and sadness, such as Shiva Asar B'Tamuz and Tisha B'Av. How is Yom Kippur different, and what is the nature of this day?
In many respects, the customs of Yom Kippur seem to have a sad tone. We do not eat or drink, engage in marital relations, wash ourselves, or apply any ointments or perfumes. These types of restrictions are generally associated with sad days, as is the fifth prohibition of the day: not wearing shoes.
Interestingly, there is another instance of removing shoes, one completely unrelated to fasting: when Moshe Rabbeinu prepares to hand over the mantle of leadership to Yehoshua. A fascinating parallel between these two great leaders is that both of them were instructed, at different points, to remove their shoes. Moshe, when he first spoke to Hashem, was told to remove both his shoes from his feet. Yehoshua, on the other hand, was told by a malach Hashem to remove one shoe. Aside from the curious difference between Moshe and Yehoshua, the command to remove their shoes in general begs the question: What is the meaning behind "removing one's shoes," and what is the connection between these incidents and removing our shoes on Yom Kippur?
Arguably the most important concept in life, though often misunderstood, is the nature of the soul. Most people believe that they "have" a soul, some spiritual essence they possess within themselves. However, the deeper Jewish sources reveal a profound spiritual secret: you don't have a soul, you are a soul. In other words, the soul is not an aspect of your self, or some spiritual component of your being; it is your very self. You are a soul, a consciousness, a spiritual being. When you say "I", you are referring to your soul, your inner sense of self. You have a body, emotions, and an intellect, all different aspects and expressions of your soul. But you are a soul, a neshama, an infinitely expansive consciousness.
A soul is angelic, perfect, pure, and transcendent. This is what Chazal refer to as your "fetal self", when you were still in the womb, just before entering this physical world. However, the moment one enters this physical world, the infinite expansiveness of the soul is confined within the physical body. The body is the container of the soul, but it is also the soul’s vehicle and tool, allowing the soul to manifest its will in this world. This is our mission in life. We enter this world with an undeveloped vehicle, our limited body. The soul, our existential self, is already perfect, but we don't yet have access to the fullness of our true self. As we journey through life, we tap into greater and greater aspects of our soul, our self, and we must then manifest them into the world through our physical bodies. In doing so, we uplift our physical vessels, and enable them to tap into greater and greater aspects of our true self. This is the beautiful cycle of life, the endless expansion and expression of self into this physical world.
While this perspective is both powerful and fundamental, its implementation is elusive, and perhaps humanity's most central struggle. Many people believe that they are a body, a physical, finite being. Having forgotten our true selves, we are born with the illusory belief that we are only that which we can see. We look in the mirror, seeing only flesh and bone, and we believe that this is all that we are.
However, this is merely our starting point. The turning point in life is the moment we realize that we are angelic souls in a physical casing. We are not physical beings attempting to have a spiritual experience, we are spiritual beings trying to uplift our physical experience. This is the central theme of Yom Kippur.
Yom Kippur is the one day of the year when we completely free ourselves of our physical limitations, embracing our angelic self. This day embodies true teshuva, when we return to our ultimate root, to our spiritual, perfect self. Chazal characterize Yom Kippur as the one day of the year when we have the ability to become a malach (angel). On this day, our lower self and physical urges are powerless, they cannot bring us down. They formulate this idea through the following gematria: "Ha'Satan"- the evil inclination, has the numerical value of 364. There are 365 days in the year, but the Satan only has power on 364 of those days. Yom Kippur is the one day where the Satan, the Yetzer Hara, has no power over you. On this day, you can completely transcend and experience angelic perfection. 
This is why there is a custom to wear white on Yom Kippur, and why married men wear a kittel. A neshama is a pure, radiant light, and on Yom Kippur we express our purity. We set our focus on the spiritual root alone, transcending the opaque, physical world. This is also why there is a custom to enter the mikvah on Erev Yom Kippur. The Mikvah is an experience of rebirth, returning to our angelic root, to our fetal perfection, where we learned kol ha'Torah kulah in the amniotic waters of our mother's womb. 
This idea also explains an unusual feature of the Yom Kippur tefillah. On all other days of the year, we whisper "baruch shem kevod malchuso li'olam va'ed" to ourselves. However, on Yom Kippur, we all proclaim this phrase out loud. Chazal explain that the reason we usually whisper this phrase is because it is a phrase that the malachim say. As limited human beings, we may not have the ability to properly express its meaning, so we whisper it instead. On Yom Kippur, however, we are malachim! As such, we no longer have any doubt, and proclaim this phrase out loud.
There is a paradoxical relationship between the body and the soul:
If the soul and body are complete opposites, how do they manage to coexist as one? One would expect them to repel each other, like two opposite sides of a magnet.
This is the powerful purpose of food. There needs to be something to keep your soul attached to your body, some kind of "glue". Eating food generates the energy which keeps your neshama connected to your body. That is why the lack of eating has the opposite effect. What happens when you don't eat? You become faint. What happens if you continue to fast? You will pass out. And if you still don't eat, your soul will leave your body and you will die. Eating maintains the connection between your soul and your body; it is what keeps you alive.
This is the depth behind the phrase "u'mafli la'asos- Who performs wonders”, that we recite in Asher Yatzar (the blessing we recite after using the bathroom). What “wonder” are we referring to? Many commentators  suggest that it is the wondrous paradox that our soul, infinitely transcendent, can remain connected to our bodies, a physical, finite vessel. We mention this specifically after using the bathroom because we have just filtered out the unneeded parts of what we ate. or drank, the very means of forging the connection between body and soul.
We can now understand the concept of fasting, especially on the day of Yom Kippur. On Yom Kippur, we attempt to live as malachim, completely transcending the physical world. We therefore fast, allowing our soul to somewhat transcend our body, enabling us to experience one day of living in an angelic state.
This principle sheds light on all the issurim of Yom Kippur. We don't engage in the physical world because Yom Kippur is a day of transcending the physical aspects of human experience. There is, however, one halacha that still requires elucidation: why do we remove our shoes on Yom Kippur?
The Nefesh Ha'Chaim explains the profound spiritual concept of shoes. The body uses the shoe as its way of traveling through the world. The lowest part of your body rests in your shoes, and this allows you to walk. This relationship between the body and shoe is the same relationship as that of the soul and body. You are an angelic soul, a neshama, but the lowest part of your angelic self resides within your physical body, serving as your container, your "shoe", and this what allows you to “walk” through the world, to interact with the physical, and actualize your potential. Na'al, the Hebrew word for shoe, also means to "lock", because shoes lock your feet in and allow you to walk around. So too, your body locks your angelic self in, allowing you to use your body to navigate this physical world.
The Nefesh Ha'Chaim explains that the spiritual concept of removing our shoes represents transcending our physical bodies. Taking your "foot" out of your "shoe" represents removing your angelic soul from your body. On Yom Kippur, we aim to transcend our physical bodies and embrace our angelic selves. We therefore remove our shoes, our "physical vessels".
As we previously mentioned, both Moshe and Yehoshua were commanded to remove their shoes. Moshe was instructed to remove both shoes, whereas Yehoshua was commanded to remove one. Based on the previous discussion, let us now try to understand this mysterious command.
Prophecy was an other-worldly experience. Hashem expanded the navi’s consciousness, enabling him to connect to a higher dimension of existence, one that lies far beyond the limitations of time and space, far beyond the capacity of the normal human mind. In doing so, the navi became capable of experiencing lofty ideas and intellectual truths which he would otherwise not have access to. These ideas and truths would then filter down through the navi's intellect and get translated through his imaginative faculties, resulting in his unique and subjective experience of those objective truths. In a very deep sense, nevuah was an other-worldly and angelic experience of the spiritual world that a navi experienced while still in this world.
This is why Moshe was commanded to remove both of his shoes before receiving nevuah at the burning bush. Before transcending into the spiritual and angelic realm, Moshe had to remove his shoes, to loosen the connection between his soul and his body.
The Malbim explains the difference between Moshe and Yehoshua:
With this deep understanding of shoes, we can understand chalitzah, one of the strangest and most misunderstood halachos. When a woman is childless and her husband dies, if the husband has a brother, he has the opportunity to perform the mitzvah of yibum, where he marries his brother's widow. If, however, he refuses to perform yibum, he can choose to perform chalitzah instead. In this peculiar process, the woman removes his shoe and spits on the ground in front of him, freeing the brother of the responsibility to marry her. What is the meaning of this unusual halacha?
As the Ramban explains, children are the continuation and expression of their parents. Just as branches on a tree stem from a single seed, children are the branches that grow out of their parents. This is also why the Gemara refers to children as the “feet” of their father (brah karah di'avuhah); just like feet carry you through this world, children carry on their parents’ spiritual essence and legacy, even once they have left this world.
When a man dies without any children, there is no one to carry on his soul through this world. His existence in this world has ceased. As such, there is a mitzvah for his brother to marry his wife and bring down an aspect of his deceased brother's neshama, to give him a child to continue his journey in this world. This is the greatest gift that both the deceased man's wife and brother can give him.
The first historical expression of this halacha stems from Yehuda, who married Tamar once both of his sons died childless. In this case, Yehuda lost not only one son, but two. When Yehuda married Tamar, for which son did he fulfill yibum? The answer is beautiful. He fulfilled yibum for both, which is why they had twins! 
If, however, the brother refuses to perform yibum, he is in essence refusing to give his brother any expression in this world. For this reason, the widow takes his shoe and spits over it. The brother refused to provide her husband with a body (shoe) for his neshama, a second chance for him to be expressed in this world, so she takes off his shoe and spits at it in disgust. 
Chanoch is another fascinating example of this principle. Chazal inform us that Chanoch made shoes. Why does the Torah deem it necessary to share this seemingly trivial fact?
Generally, death occurs when a human being’s angelic soul- the self and consciousness- leave their physical body behind and ascend to shamayim, the spiritual realm. Chanoch, however, did not follow this pattern. Rashi quotes the midrash stating that Chanoch was the most spiritual person in his generation, so spiritual that he was able to uplift his physical body (his shoe) to the extent that he ascended straight to shamayim, without having to die and leave his physical body behind. Chanoch devoted his life towards uplifting "shoes", towards uplifting his physical body to fully reflect the spiritual greatness of his soul.
The Ramchal  explains that Eliyahu Ha'Navi and Moshe Rabbeinu also managed to attain this lofty, transcendent spiritual level. The spiritual mechanics of this are quite profound. The Ramchal elsewhere explains  that prior to Adam's sin, humans were on a more transcendent level and animals were on the level of humans nowadays. This is why the nachash sounds so "human", it is because the nachash was on the level of current human beings. Adam, however, was on a much higher level. His "body" was on the level of our current spiritual level of self, and his “spiritual” level of self was on a tremendously more elevated level than ours. In other words, his body was itself a spiritual entity which contained a much higher form of Neshama. The proof for this is as follows: Adam's physical body resided in Gan Eden. After we die, our neshamos ascend to Gan Eden until Techiyas Ha'Meisim (the resurrection of the dead). It is therefore clear that our souls are on the same level as Adam's original body.
It is also interesting to note that the Gemara  discusses how the angel Sandalphon is the angel who bridges the gap between the spiritual and physical worlds. It should be no surprise that the angel responsible for connecting the spiritual to the physical has the word "shoe" in his name. A name represents essence, and this angel’s name reflects his mission in life, to connect the spiritual to the physical vessel, the concept of shoes.
There is one last aspect of Yom Kippur which ties together everything we have developed, and this is the unique nature of the Kohen Gadol's avodah on Yom Kippur. There are two unique elements of this avodah that require explanation. First, the Kohen Gadol enters the Kodesh Ha’Kodashim on Yom Kippur and performs the unique avodah of the ketores. This is problematic because no man is allowed to enter the Kodesh Ha’Kodashim, a place that Chazal describe as being beyond space and time. Second, the Kohen Gadol proclaims the Shem Ha'Meforush, the uniquely holy name of Hashem, a name which no man is ever allowed to say. How, then, can the Kohen Gadol express this name on Yom Kippur?
The answer is as follows. During the year, no human being is allowed to enter the Kodesh Ha’Kodashim, not because it is forbidden, but rather because it is impossible. The Kodesh Ha’Kodashim is completely transcendent, beyond space and time. The same is true for the Shem Ha'Meforush. It is a transcendent name, beyond time and space, unable to be uttered in the physical world. Speech is always the limited expression of abstract and spiritual concepts, and the limited tool of speech cannot convey the truth and full essence of the Shem Ha'Meforush. Therefore, human beings are not able to enter the Kodesh Ha’Kodashim or utter this special name.
On Yom Kippur, however, we transcend our limited status as normal human beings and embrace our transcendent and angelic selves. As such, we no longer have these limitations. On this special day the Kohen Gadol represents all of Klal Yisrael as angelic beings as he enters the Kodesh Ha’Kodashim and verbalizes the Shem Ha'Meforush on our behalf.
This is the unique opportunity that Yom Kippur presents: to transcend, to experience the infinite. Unlike other fast days, it is not a day of suffering and mourning, but one of spiritual transcendence. As the famous quote goes: On Tisha B'Av, who can eat, on Yom Kippur, who needs to?" This is why the Rambam states  that on Yom Kippur we "rest" from eating. This is not a day of prohibition and suffering, it is one of completely embracing the spiritual, tapping into our absolute root, our truest sense of self.
The transcendent experience of Yom Kippur lays the foundation for the rest of the year. While the physical can be destructive if misused, the ideal is not to completely transcend the physical, but rather to use the physical in order to reflect something higher. Our goal as humans is not to escape the physical, but to use it as a means of connecting to the transcendent.
This is the key behind the process we undertake throughout the Yamim Noraim. We first experience Elul, then Rosh Hashanah, and then Yom Kippur, a developmental process of elevating ourselves higher and higher above the physical world and deeper and deeper into the spiritual world. Only once we establish this transcendent root can we then re-immerse ourselves into the physical world, but this time on an entirely new level. Sukkos, which immediately follows Yom Kippur, embodies this lesson in embracing the physical. Our root must be transcendent, grounded firmly in the spiritual, and then atop that foundation we can descend into the physical and use it in a transcendent way.
May we be inspired to fully experience our angelic selves this Yom Kippur, and then infuse the totality of our spiritual acquisition into our physical life, elevating our actions and intentions as we move this physical world towards its ultimate spiritual root.
 Taanis 4:8.
 Tikkunei Zohar, Tikkun 20 and 21.
 Shemos 3:5.
 Yehoshua 5:15.
 See Niddah 30b.
 And in the lunar year, there are 355, plus the 10 of Aseres Yemei Teshuva.
 Yoma 20a.
 See chapter on Parshas Noach, section: “Mikavah: Personal Re-Creation”.
 For more on this, see chapter on Parshas Tzav, section: “Eating: Connecting Body and Soul”.
 Such as the Beis Yosef.
 Physical relations, eating, washing the body, and wearing perfume all require one to engage in the physical.
 Nefesh Ha’Chaim 1:5, note 6.
 Chazal discuss the five levels of every soul. The lowestpart of the soul, the nefesh, is the part that completely resides within the body, just as the foot, the lowest part of the body, resides within the shoe.
 The prophetic experience is beyond space and time. This explains how a navi can become aware of future events that have not yet occurred. Within this transcendent realm of experience, time itself breaks down. Past, present, and future melt into one continuum. This raises the conflict between free will and foreknowledge, a question that is beyond the scope of this chapter.
 Av (father) also means root, while toldos (children) also means branches.
 In essence, this is a form of gilgul.
 The Ramban explains that before Matan Torah, even a father was able to perform Yibum for his son. This is fitting, as their spiritual bond (and spiritual DNA) is even closer than that of brothers.
 The mouth represents the organ of connection. Saliva, and the mouth, are used for eating, creating the connection between body and soul. Since the brother refused to create the connection between her late husband's soul and a body, she uses the mechanism of connection, her saliva/mouth, to express her disgust at his failure to reconnect body and soul.
 Practically, yibum is no longer performed (as we are no longer on the level where it can properly be done), and chalitzah is therefore performed in its stead.
 See midrash on Bereishis 5:22.
 Ramchal, Da'as Tevunos 70.
 Da'as Tevunos- 126.
 Chagiga 13b.
 See chapter on Parshas Eikev, section: “Concentric Layers of Time and Space”.
 Hilchos Shevisas He’Asor 1:4.
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