Shabbos: The Darkness Inside the Light

Understanding Shabbos through the lens of Parashas Vayishlach

Dec 07, 2025

Rav Eliyahu Dessler once showed up to a lecture with a large white oak tag that had a single black dot in the center. He asked the students, “What do you see?” They answered immediately. A black dot. Rav Dessler responded, “Do you not see all the white around it?” His point was simple. Make sure to see the white part of life, the clear and shining candle of life.

The story of Yaakov Avinu is fascinating. Each time he seemed to reach for perfection, for shleimus, something pulled him back. His life hints that his mission was to reveal how growth continues even when life presents endless excuses to remain stagnant.

Two great spiritual movements shape Yaakov’s life. They stand in clear contrast: last week’s parashah, Vayetzei, and this week’s parashah, Vayishlach.

In Vayetzei, Yaakov left his home and entered the uncertainty of exile. He was alone, afraid, penniless, and unprotected. Yet in that very darkness he was forced to search for light. Leah became his guide, teaching him how to uncover light in hidden places. This light is the light of Shabbos, the Ohr HaGanuz, and Yaakov received the task of holding it.

In Vayishlach, the rhythm changes. Yaakov returns to Canaan with that light, a light reshaped and deepened by the years of concealment. As we say in Lecha Dodi, “Kumi tzei mitoch hahafecha,” this can be understood as leaving the upheaval before entering the light, yet also as a reminder that the upheaval itself carries the passageway to redemption.

Yaakov arrives “shalem,” complete in body, in wealth, and in Torah1. Rav Tzadok notes that Avraham and Yitzchak reached the levels of “bakol” and “mikol,” a taste of Shabbos-like fullness, while Yaakov alone says “yesh li kol,” “I have everything.”2

The Noam Elimelech adds that the holiness Yaakov refines in Lavan’s house creates spiritual currents that soften Esav, so the encounter with his brother reveals the inner work that took place in exile. As this inner light enters open space, it begins to reveal the shadows beneath the surface of apparent wholeness.

Yaakov does more than contend with the Ohr. He searches for it, claims it, and treats it as his own. That makes the next turn in the story even more striking. Just as this light seems to settle and his spiritual ascent gains strength, the shadows appear again and the threat of darkness rises once more.

He prepares to meet Esav and then wrestles with Esav’s ministering angel. The struggle unfolds in the last hours of the night, moments before dawn, when light begins to seep in yet darkness still hangs over the horizon. It is bright enough to reveal what the night tried to hide.

As we follow the parashah, Yaakov reconciles with Esav. He receives the name Yisrael. His family surrounds him. The long night seems finally over, and the story appears ready for calm. Instead, this moment opens the door to a deeper and more complex drama, the saga of Dina and Shechem and later that of Yosef. Once again, just when Yaakov reaches a state that feels like shleimus, he enters a new descent.

His daughter Dinah is abducted. The violent response of Shimon and Levi destroys any hope of building a cooperative society in Shechem.3 Yaakov recoils from their actions and fears the consequences that may follow. He rises again, only to lose Rachel on the road to Efrat, a grief that the Torah never describes him fully recovering from. Soon after, Reuven interferes with his father’s marital arrangements and disrupts the family order. The light has returned, yet that very light now reveals fractures that had been present all along.

The Sfas Emes understands Shechem as a place where “shem kevod malchuso,” the honor of Malchus Hashem, seeks expression, a setting that resembles a Shabbos-like return to holiness. Such a place calls for boundaries and care. When Dina steps past those boundaries, when the movement outward stretches beyond its proper measure, the light itself draws out the hidden darkness beneath it.

One who stands in strong light often fails to see the darkness nearby, while one who sits in darkness can notice the distant glow. Yaakov, newly returned to the radiance of the land, encounters the full weight of the shadows only once they break open in front of him.

These two movements form a pattern that reaches beyond Yaakov’s lifetime. Indeed, they have become the pattern of Jewish history. First, the soul gathers sparks in the darkness of exile. Then, as the light returns, a subtler darkness rises within the light itself. We will see next week that this pattern continues with Yosef and Yehudah and then flows through the generations.

Vayetzei teaches how to uncover sparks in the night. Vayishlach teaches how to remain steady when sunrise reveals the imperfections that still seek healing. These are two distinct experiences. They form two Shabbos-modes and two stages of the soul.

The first is the Shabbos that comforts, the hidden spark that glows within exile.

The second is the Shabbos that confronts, the bright light that reveals what still waits beneath the surface.

If one had to choose the core message of Vayishlach, it comes down to a single word: “levado.” When Yaakov remains alone at Nachal Yabok, the Torah emphasizes that solitude4.

Rav Chaim Walkin explained5 in the name of Rav Chaim Shmuelevitz that being alone belongs to the highest rung of spiritual attainment. Hashem too is called alone, venisgav Hashem levado6. Levado describes a state in which a person stands without external support and holds on to spiritual truth through inner strength alone.

Rav Yaakov Kamenetsky explains that only rare individuals maintain their level under such conditions, and Yaakov stands among them7. Shabbos is a time when our inner essence emerges and illusions fall away. In that light, loneliness becomes a form of clarity rather than abandonment.

The Noam Elimelech adds another layer. “Vayivaser Yaakov levado” describes an inner solitude in which Yaakov gathers even the faint “dust” (ויאבק) of past missteps, the slightest moral residue, and raises it through teshuvah me’ahavah until it stands before the Kisei HaKavod. Yaakov’s struggle by the riverside is not only with an angel. It is also with his own story, with the small, hidden places that still call for lifting and healing.

At dawn, Yaakov receives a new name: Yisrael. Rashi explains that the name Yaakov reflects a path that moves through subtlety and strategy, while Yisrael reflects a stance that receives blessings openly, like a prince who stands upright8. The shift signals a move from skirting around darkness to moving through it directly. To live as Yisrael is to face reality with courage and clarity, to accept that struggle belongs at the center of life, and to stand within that struggle without losing oneself, while still seeing the wider frame around it. This is why Yaakov receives the name Yisrael at dawn. The struggle becomes the source of his clarity.

The Beis Yaakov describes this transition through the change in the pronunciation of the place of this battle, which shifts from Peniel to Penuel, from a hidden yud to an expanded vav. Yaakov’s years in exile form a stage of constriction. He serves Hashem within limits, gathers light within struggle, and carries that light in a way that remains mostly concealed. When he becomes Yisrael, that hidden light expands and begins to shine. The moment the light spreads, it illuminates everything around it, including what previously remained unseen. What feels like rupture is the natural consequence of light emerging from earlier concealment.

Elsewhere, the Beis Yaakov explains that Yaakov embodies a form of shleimus that reaches beyond the angels. Angels hold immense spiritual power, yet each one remains locked in a single trait or function. Human beings, and Yisrael in particular, can hold many qualities at once. Yearning and fear, strength and softness, clarity and confusion, all find a place within one soul. Yaakov’s greatness lies in this capacity for integration. His new name, Yisrael, signals that ability to turn contradiction into depth, to receive darkness as material that can become fuel, and to move through complexity toward a larger, more honest truth.

Shleimus means the capacity to hold every force, in light and in shadow, without falling apart.

Rav Soloveitchik sees in this moment a way to understand Jewish destiny9. To be Yisrael is to wrestle with God and with humanity, without retreat from either side. The story of the Jewish people unfolds inside that tension. We live inside the world and struggle faithfully with what we find there, while remaining wary of the noise that surrounds us and rising above it, levado.

Overcoming challenges is what gives a person the name Yisrael. Only because we are Yisrael, and we understand that life unfolds across many layers, do we find the strength to rise through struggle and see that everything is possible.

This movement reaches far beyond a private world of spiritual experience. Yaakov still needs to walk toward Esav. Chazal describe his preparation in three parts: he divides the camp, he prays, and he sends a gift10. He responds with strategy, tefillah, and generosity together. He weaves kedushah into his battle plan. In this moment holiness serves as the inner framework that guides his engagement with fear.

Even so, the deepest test lies ahead. The central challenge of Vayishlach does not come from solitude in the dark, but from standing in light that exposes new shadows. It is one thing to feel alone when everything appears broken. It is a different kind of loneliness to feel that way when life finally looks whole. This is the experience of Yaakov in the land. The light returns, and along with it the demons that now step out of hiding.

We find throughout the seforim the idea of spiritual contrast, that an abundance of spiritual light brings out that which still awaits the light. The Sfas Emes writes that when the Ohr of Shabbos intensifies it reveals the corners of the self that still require healing11. The Mei HaShiloach teaches that divine illumination draws contradictions to the surface so they can be elevated. Rav Kook describes every ascent as a process that releases resistance from the depths of the soul, so the feeling of regression often signals the pain of expansion12. The Tanya explains that the joy that arises after wrestling with inner darkness reaches deeper than joy that comes without effort13.

All of these teachings echo through Yaakov’s story in Vayishlach. He returns to the land with a new light, and that light instantly reveals places that still hurt.

All of this returns us to Shabbos. There is the Shabbos of Vayetzei, a Shabbos that offers comfort inside exile, the Shabbos when a ladder appears in the night and a hidden spark of light keeps faith alive. There is also the Shabbos of Vayishlach, a Shabbos that confronts, a Shabbos when the light that comes with shleimus grows strong enough to reveal every lingering shadow. One Shabbos soothes, the other demands. One holds the weary traveler, the other asks him to look honestly at what still needs to change. Shabbos contains both modes because the world contains both modes. Geulah draws energy from both.

The Beis Yaakov explains that some of the deepest forms of growth arise during times and through doing mitzvos that remain beyond our understanding, when we accept the weight and continue to carry it. In truth, those burdens, the weight of doing something without clarity or living through an event that seems to defy explanation, are the very things that carry us. They press the soul into the shape that will one day live in an existence of pure Shabbos, a “yom shekulo Shabbos.”

In this light, the Beis Yaakov explains Yaakov’s fear of harming Esav. As long as Esav stands in the world, Yisrael must move among the nations, live under pressure, and remain distinct. Through that difficult refinement, they earn a measure of light and blessing that could not appear in any other way.

One of my siblings has long championed living out of town for this reason. In a dense, like-minded community in town, where everyone around you looks and lives the way you do, a person easily blends into the crowd. In an out-of-town setting, where many neighbors feel indifferent to Torah and mitzvos, the role shifts. You stand out simply by staying loyal to your values. You become the point of difference. You become the light.

This brings us back to the question of individuality itself. In the story of Creation, almost everything is described the same way. Each part of the world comes into being למינהו, according to its type. Trees follow trees, animals follow animals, every species repeats its own pattern. There is only one exception. When the Torah speaks about the creation of human beings, it does not say למינהו. Humanity is not presented as “according to its kind,” because we are not meant to be copies. We are meant to grow into our own inner shape.

Rav Elya Weintraub zt”l explained that our nature is to absorb the world around us and to blend into whatever environment we find ourselves in. Our avodah is to discover and protect the part of ourselves that does not dissolve into the crowd. This is the levado of Yaakov. He stood alone, and that loneliness was not a flaw. It was the space that allowed him to become fully himself.14

The light found in the darkness is precious. The courage to remain in the light when it reveals darkness is transformative. Together they form the path to redemption.

As mentioned above, Chazal describe the time of geulah as a “yom shekulo Shabbos.” That day does not erase the night. It gathers every spark collected in the night and every shadow purified in the light, revealing what they were shaping all along. It is the light of Shabbos that allows no darkness to remain outside it, because every darkness has already become part of its glow.

As with Rav Dessler and his black-dot presentation, Yaakov Avinu was able to zoom out and see that the upheavals in his life were merely scattered black dots, and that he was surrounded by light, the light of Shabbos. The Ohr was all around him. He did not zoom in on the darkness. He saw it as a tiny speck on an oak tag of Ohr.

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