The Seven Paradoxes of Yom Kippur
Seeing Through a Day of Joyful Paradoxes
According to Pharrell Williams, the height of happiness is to feel like a “room without a roof.” Strange as it may sound, Yom Kippur is meant to be the happiest day of the year. The Mishnah teaches, “There were no better days for Israel than the 15th of Av and Yom Kippur.”1
So according to Pharrell, Yom Kippur is the day to feel like we are in a room without a roof. Why is this?
There is only one day a year that begins with a matter of simcha. Not Pesach, the time of our freedom, and not even Sukkos, our official זמן שמחתנו (time of our joy). Only Yom Kippur opens with a pasuk that stirs all hearts:
“אור זרוע לצדיק ולישרי לב שמחה”
“Light is sown for the righteous, and for the upright in heart, there is joy.”
The Mishnah continues:
וכן הוא אומר, (שיר השירים ג) ‘צאינה וראינה בנות ציון במלך שלמה בעטרה שעטרה לו אמו ביום חתנתו וביום שמחת לבו’.”ביום חתנתו” – זו מתן תורה.
And so it says, “Go forth and see, O daughters of Zion, King Solomon with the crown wherewith his mother crowned him on the day of his wedding, and on the day of the gladness of his heart.” “On the day of his wedding” – this is the giving of the Torah. (Shir Hashirim 3)
Rashi immediately clarifies:
זו מתן תורה – יום הכפורים שניתנו בו לוחות האחרונות
This is the giving of the Torah – “this refers to Yom Kippur, when the second Luchos were given.”
The Torah was not actually given on Shavuos but on Yom Kippur, the day representing the “Wedding Day” between Hakadosh Baruch Hu and Klal Yisrael. This may seem surprising, as Yom Kippur is generally associated with fasting, repentance, and a sense of solemnity. At first glance, it doesn’t seem like a particularly joyous day—let alone the most joyous day of the year.
In fact, the Vilna Gaon includes joy among the forms of affliction one should observe on Yom Kippur.2 This is alongside other traditional afflictions like abstaining from bathing and not wearing leather shoes. It’s intriguing that joy is considered an affliction on this solemn day.
Yom Kippur is indeed a day rich with paradoxes, offering deep insights into our understanding of repentance, human nature, and our relationship with Hashem. Let’s explore a few of these intriguing contrasts:
Individual vs. Communal: Yom Kippur is deeply personal, a time for individual introspection and teshuva. Yet, the plural language of the Vidui emphasizes the interconnectedness of the Jewish people. It’s a day of communal prayer experienced on a profoundly personal level.
Human vs. Angelic: On Yom Kippur, we grapple with our human flaws while simultaneously aspiring to an angelic purity, even reciting the Shir Hayichud, just as angels do.
Physical Abstention vs. Spiritual Nourishment: Although we abstain from food and drink, Chazal taught that we are spiritually nourished on this day, as if sustained by manna, like angels.3
Joy vs. Mourning: The emotional landscape of Yom Kippur spans from the joy of the Kohen Gadol’s successful exit from the Kodesh Kedoshim to the profound sorrow over the destruction of the Beis HaMikdash and the martyrdom of the Asarah Harugei Malchus.
Essence of the Day vs. Active Repentance: Yom Kippur itself brings atonement, yet we engage in intense tefillah and fasting. If the day inherently atones, why not treat it as an ordinary day, relying solely on its power?
Children vs. Servants: In our tefillos, we describe ourselves as both children and servants of Hashem. Which role truly defines our relationship with Him?
The Closing Shofar: After a day immersed in teshuva, the shofar’s blast at the end seems redundant. What is the significance of this shofar?
A paradox conveys that reality is often complex and resists being reduced to a simple, binary perspective. Life often demands that we hold multiple truths at once, embracing a fuller picture. In many ways, each of us embodies this sense of paradox.
In 1951, Edward Simpson introduced a phenomenon in statistics now known as Simpson’s paradox. This occurs when a trend appears consistently across several groups of data but reverses or disappears when these groups are combined. It’s a common occurrence in social science and medical research, where frequency data can sometimes be misleadingly interpreted as causal. 4
A classic example involves baseball batting averages: one player might have a higher batting average than another player over a series of years, yet, when all those years are combined, end up with a lower overall average. This can happen when there’s a significant difference in the number of at-bats each year.
Mathematician Jordan Ellenberg suggests that calling this a paradox may be misleading, as there’s no real contradiction. Instead, Simpson’s paradox teaches us to hold multiple viewpoints at once—considering both the parts and the whole together, rather than choosing one perspective over the other.
What is true in mathematics often holds in Ruchnius as well. Let’s explore how this principle is reflected in Yom Kippur.
Rabbeinu Yonah emphasizes that Yom Kippur carries a mitzvah of simcha, just like any other Chag. However, because it is a fast day, the joy and celebratory meal associated with this mitzvah are moved to Erev Yom Kippur.5 This shift highlights a paradox: how can the solemn feelings of awe and confession coexist with the simcha of the mitzvah? The Talmidim of Rabbeinu Yonah offer a profound explanation. They point out that while fear and joy might seem to be opposites in human interactions—where fear often leads one to withdraw from another—this dynamic is different in our relationship with Hashem.
In contemplating Hashem’s greatness, a person feels awe, which paradoxically brings joy. This joy comes from the awareness that awe for Hashem awakens one’s desire to fulfill mitzvos. Through this process, a person rejoices because he understands the profound reward that accompanies his service. Therefore, on Yom Kippur, awe and joy are not conflicting; rather, they actually complement each other. The more deeply one experiences the awe of the day, the greater his elation at the opportunity to serve Hashem in this elevated state. The more he is joyful, the more completely he fulfills the mitzvos of Yom Kippur.6
Rav Soloveitchik elaborates on this theme by pointing out that whenever the Torah mentions simcha, it places it Lifnei Hashem—in the presence of God. True joy arises from experiencing Hashem’s presence. Thus, on Yom Kippur, standing in judgment before God, our feelings of awe are accompanied by authentic simcha, rooted in our connection to Him.7
Rav Kook adds another dimension, explaining that in an ideal world—before the sin of Adam—Olam Haba and Olam Hazeh would be one and the same. However, sin introduced a division between them, creating a gap where the pure illumination of the World to Come does not fully penetrate our present world. Teshuva bridges this gap, drawing us closer to the sanctity of the World to Come. On Yom Kippur, we elevate ourselves above the mundane, distancing from the physical world to align ourselves more closely with Hashem, on a level of the World to Come. Rav Kook further explains that the days between Yom Kippur and Sukkos help us reintegrate, balancing the spiritual elevation of Yom Kippur with a return to the world we live in.8
Rav Moshe Shapiro takes this concept even further, explaining that on Yom Kippur, we attain a status akin to Olam Haba. He describes Yom Kippur as a “field trip” into the World to Come. True teshuva turns our sins into merits, drawing us closer to Hashem and to the essence of Olam Haba. While Shabbos offers a taste of Olam Haba, it is Olam Haba coming down to us, so we still partake in physical food. In contrast, on Yom Kippur, we ascend to Olam Haba, sustained by spiritual nourishment akin to manna, which has neither taste nor form but fulfills our needs just the same.9
Rabbi Immanuel Bernstein reflects on the Midrash, which draws a comparison between the Jewish People on Yom Kippur and the angels:
The Midrash10 enumerates the comparisons between us and the angels:
מה מלאכי השרת אין להם אכילה ושתיה, כך ישראל אין להם אכילה ושתיה ביום הכיפורים, מה מלאכי השרת נקיים מכל חטא כך ישראל נקיים מכל חטא ביום הכיפורים, מה מלאכי השרת שלום מתווך ביניהם כך הם ישראל שלום מתווך ביניהם ביום הכיפורים
Just as angels do not eat or drink, so too the Jewish People on Yom Kippur do not eat or drink. Just as angels are clean of all sin, so too the Jewish People on Yom Kippur are clean of all sin. Just as with the angels peace resides between them, so too with the Jewish People on Yom Kippur peace resides between them.
The peace and togetherness that exist among us on this special and holy day are an integral part of the exalted and angelic status we are trying to attain.
There is a beautiful and important message being communicated here. Yom Kippur is in many ways an intensely personal day. There is much introspection and soul-searching that needs to be done, and that has to happen with our souls, not with those of others. With that, we should not lose sight of the fact that we are all part of the Jewish People, and it is as a people we come together on this day to receive atonement — “Before Hashem.”11
This idea underscores the unity that defines Yom Kippur. While it is indeed a day of profound personal introspection, we must remember that we stand together as one people before Hashem, seeking forgiveness as a collective.
As we begin Yom Kippur, we remind ourselves that this is a day of simcha. It is not only a day of teshuva but also one of joy, as emphasized by the Shehechiyanu we recite. Throughout the year, people often turn to teshuva driven by fear, sorrow, or personal need. But on Yom Kippur, teshuva is driven by joy. We stand as the kallah, the bride of Hashem. On this day, Hashem invites us to ascend to the “executive suite,” a metaphorical place of closeness and elevation.
In the words of Rabbi Sacks, “More than Yom Kippur expresses our faith in God, it is the expression of God’s faith in us.”12 Today, as we return to Hashem, it is with the knowledge that He believes in us, meeting our teshuva with a loving embrace — we just need to do our part.
Yom Kippur marks the day we received the second set of Luchos. It is the day that we received the chance not only to start again, but to elevate ourselves to understand the Torah on a deeper level. In kabbalistic terms, Yom Kippur corresponds to the level of Binah, which involves recognizing that things cannot always be understood at face value. When faced with a paradox, Binah guides us to see each element within the broader context, leading to a harmonious synthesis. This synthesis is known as Chochma, where the distinctions between Olam Hazeh and Olam Haba fade, allowing them to align as one unified reality.
Rav Soloveitchik writes that the final shofar of Yom Kippur is our silent, desperate cry:
“As the final minutes of Yom Kippur are upon him, he yells Shema Yisrael, then Baruch Shem, and finally Hashem Hu Elokim. Yet, he still feels frustrated and dissatisfied in order to adequately express his deep longing when words have cruelly failed him, he feels the compulsion to release an instinctive, inarticulate cry. in the seconds before God once again retreats into obscuring cloud, man must urgently express what he could not verbalize in an entire day of prayer. He sounds the shofar as a response to the ultimate futility of verbally expressing his needs.13
I’d like to offer a further explanation. The Torah14 teaches that in the Yovel year, all slaves go free—a release that happens on Yom Kippur with the sounding of the shofar.15 Earlier, we questioned why we blow the shofar of teshuva on Yom Kippur. Perhaps the question could be reframed: why are we blowing the shofar of redemption on this day?
When we reach the peak of our tefillah, the moment where words fall short of articulating our deepest feelings, regrets, and aspirations, this is when the shofar is sounded. At this point, we are no longer mere servants; we return home as Hashem’s beloved children, Banim. Hashem has mercy on us as a father to his children. It is in this state that Olam Hazeh and Olam Haba realign.
Just as a chassan and kallah retreat to the yichud room after the chuppah, when there is nothing more to be said, so too does Klal Yisrael—having been united with the Ribbono Shel Olam—prepare for Sukkos, building our sukkahs to dwell with Hashem. For seven days, we sit in the sukkah together, culminating in Simchas Torah, where we celebrate with boundless joy, rejoicing in our renewed closeness with Hashem. Through this progression, we experience the profound simcha of realignment and the joyous dance of reconnecting with our Creator.
As Pharrell Williams describes true happiness as being like a “room without a roof,” Yom Kippur offers us this same boundless joy, unconfined by limitations. In this special moment, we stand as Hashem’s beloved children, elevated to a place where no barriers exist—only openness, connection, and alignment with Him.
May we all experience a Gmar Chasima Tova, sealing our bond with Hashem in joy, peace, and an expansive, roofless happiness.
(Originally written for Yom Kippur 5784, thoughtfully revised and refined for this year)
Taanis 26a
Chumash HaGra Vayikra 23;27
Rav Moshe Shapiro Zt’l based on Yoma 75b - In Tehila L’Moshe Vol 3 pg 237
Shaarei Teshuva Shaar 4;9
Berachos 21a - cited in Artscroll Shaarei Teshuvah
Shmona Kvatzim 7;128
Tehila Lmoshe v3 pg 238
Pirkei R’ Eliezer 46.
Ceremony & Celebration p. 85
Before Hashem pg 24
Vayikra 25;10
Rosh Hashanah 8b