Parshas Vayishlach: Shadows in the Night
There’s a quiet line in Vayishlach that holds more than it says:
“ויותר יעקב לבדו — Yaakov is left alone.”
After years of running from Esav’s hurt,
from Yitzchak’s blind spot,
from the uneven love of his childhood,
from Lavan’s manipulation,
from the patterns he learned just to survive,
the movement finally stops.
He sends everything across the river:
his family, his belongings, the familiar noise,
all the ways he kept himself moving, defended, and distracted.
Right before the night begins, Yaakov says one quiet line:
“קטונתי מכל החסדים” — I have become small from all the kindness You have given me.
He feels unsure, aware of his limits, humbled by everything he has received.
It is from that place of smallness that he steps into the night.
And in the dark that follows, something steps toward him.
The Torah calls it simply “איש — a man,” but does not identify who or what it is.
That lack of detail is intentional. The Torah gives no further description, which is why Chazal understood this moment as something deeper than a physical fight.
Chazal fill the silence with possibilities:
an angel, a spiritual force, the embodiment of Esav,
or the inner truth Yaakov has avoided for years.
Whatever it is, they wrestle until dawn,
not with words or explanations,
but through a long, honest inner struggle
between the life Yaakov built
and the truth he can no longer outrun.
When this shadow figure tries to slip back into the night, Yaakov holds on tightly:
“לא אשלחך כי אם ברכתני — I will not let you go until you bless me.”
It is not a demand for victory.
It is a plea for meaning,
for clarity,
for the blessing hidden inside the struggle.
And the blessing comes, not as comfort but as a name: Yisrael.
The word Yisrael comes from the root “sar,” which means to struggle or to persevere.
It literally means “one who wrestles with God and stays strong.”
When dawn comes, Yaakov is limping.
Not broken.
Just changed.
Walking with the imprint of the night
and the truth it revealed, now integrated and carried inside his body.
This name isn’t only for Yaakov.
It becomes the name of our whole nation, Am Yisrael.
We are a people who do not give up when things get hard.
We hold on long enough to find the blessing that is hidden inside the struggle.
The Torah shows us that Yaakov’s night is also a message about our own lives.
Every person has moments they want to run away from.
Every person reaches a night when they must stop and face what has been waiting.
Chazal and Chassidus describe moments like this in a different way.
They teach that personal growth moves through forty-nine steps we can reach through our own effort, and a fiftieth step that only opens when Hashem lifts us higher.
This is the idea behind Sefiras HaOmer.
Forty-nine days of preparing yourself.
Then day fifty, Shavuos, Matan Torah,
when Hashem gives us something higher than we could reach alone.
Forty-nine is the work.
Fifty is the gift.
There’s something about the way Yaakov says “קטונתי.”
It is a moment of humility, when a person stops clinging to the version of themselves they have been defending for so long. In that release, a new opening appears.
That openness is the work of step forty-nine, the space that allows the gift of fifty to arrive.
Fifty also shows up in Yaakov’s gift to Esav.
The Torah lists a total of 550 animals, which is fifty multiplied by the eleven children he had at the time.
It is a quiet hint that each of the future Shevatim, and through them the entire Am Yisrael, carries the ability to reach their own “fiftieth” step, a level beyond effort alone.
—
Standing here in Parshas Vayishlach I’ve been thinking about my own version of those steps.
These past eleven months have held their own kind of shadowy night,
the work and the wrestling,
the unraveling and the rebuilding,
the parts I wished away and the parts I finally learned to face.
Earlier this week, when I posted my fiftieth piece, I realized that this milestone and this parsha belong to the same journey.
In their own quiet way, they helped me feel like I reached my own “fifty” — a quiet but real shift inside, feeling held by something larger than me, a sense that I can step forward now with the work of these months, the way Yaakov stepped into the dawn, limping a little but walking as the changed man I first recognized in myself in post one.
And in our own ways,
we all have nights that reshape how we step into the day that follows.
Which is why the way Yaakov emerges from his night matters for us too.
May the moments that feel like a struggle through the night lead into the beauty of a fresh morning,
with its new perspective and its blessings.
Good Shabbos,
Berke
Yonatan Razel - Katonti