During Yakov and his family’s escape from Lavan’s house, they had to navigate their way across a river. During the crossing, some of the family’s articles had been left on the wrong side, so he sent his family ahead in the dwindling light while he stayed back to retrieve what been left behind. Alone as darkness fell, he was accosted by and fought with a mysterious figure, whom we identify as Esau’s guardian angel, one of the defining moments in Yakov’s life:

וַיִּוָּתֵר יַעֲקֹב, לְבַדּוֹ; וַיֵּאָבֵק אִישׁ עִמּוֹ, עַד עֲלוֹת הַשָּׁחַר. וַיַּרְא, כִּי לֹא יָכֹל לוֹ, וַיִּגַּע, בְּכַף-יְרֵכוֹ; וַתֵּקַע כַּף-יֶרֶךְ יַעֲקֹב, בְּהֵאָבְקוֹ עִמּוֹ. וַיֹּאמֶר שַׁלְּחֵנִי, כִּי עָלָה הַשָּׁחַר; וַיֹּאמֶר לֹא אֲשַׁלֵּחֲךָ, כִּי אִם-בֵּרַכְתָּנִי. וַיֹּאמֶר אֵלָיו, מַה-שְּׁמֶךָ; וַיֹּאמֶר, יַעֲקֹב. וַיֹּאמֶר, יַעֲקֹב לא יֵאָמֵר עוֹד שִׁמְךָ–כִּי, אִם-יִשְׂרָאֵל: כִּי-שָׂרִיתָ עִם-אֱלֹהִים וְעִם-אֲנָשִׁים, וַתּוּכָל. וַיִּשְׁאַל יַעֲקֹב, וַיֹּאמֶר הַגִּידָה-נָּא שְׁמֶךָ, וַיֹּאמֶר, לָמָּה זֶּה תִּשְׁאַל לִשְׁמִי; וַיְבָרֶךְ אֹתוֹ, שָׁם. –  Yakov was alone, and a man grappled with him until daybreak. When the stranger saw that he could not overcome him, he struck Yakov’s hip and dislocated it as he grappled with him. He said, “Let me go, dawn is breaking!” – but Yakov said, “I will not let you go until you bless me.” He said to him, “What is your name?” and he replied, “Yakov.” He said, “No longer shall your name be Yakov, for your name is Yisrael, because you have mastery with God and men, and you have prevailed.” Yakov asked, and said, “Now tell me your name” and he replied, “Why is it you ask my name?”‘ and blessed him there. (32:25-30)

The imagery of this iconic battle is that it takes place in the dark of night until dawn’s early light. Darkness is not just a description of the battle environment; it’s a description of the battle itself. Most humans are afraid of the dark, at least to some degree; our sight is the sense we depend on the most, and we cannot see well in darkness; therefore, a lack of light makes us feel very vulnerable to danger.

The Mesilas Yesharim says the trouble with darkness is not just that you won’t see something dangerous, but that you can mistake something dangerous for something safe!

In the darkness, we are surrounded by the sea of the unknown, with all sorts of hidden threats lurking in the shadows in the corner of our eye. But when dawn comes, and it surely will, the darkness dissipates, and the shadows disappear. The light of reality dispels the darkness of the unknown, and the shadowy figures can’t stand to be caught in the daylight.

When Yakov asks the figure for his name, Yakov gets an evasive non-answer, “Why is it you ask for my name?” R’ Leib Chasman intuitively suggests that this the nature of the formless enemy we fight in the battles of our minds. The Gemara teaches how at the end of days, Hashem will slaughter the Satan, and the righteous will cry because it was this gargantuan mountain they somehow overcame, and the wicked will cry because it was a tiny hair they couldn’t even blow away. The very idea of the Satan is a shorthand for what we really fight – a flicker of our reflection, constantly in flux.

The Steipler teaches that the battleground of our struggles is in our minds. Whether we’re dealing with fear or fantasy, our minds can paint such vivid pictures that do not correlate with reality. Our fears amplify how bad things can be, and our fantasies amplify how good things will be; neither include any of the pathways, tradeoffs, or consequences of reality. When someone returns home after a long time away, they might hope to finally get along peacefully and happily with their family; a newlywed couple might hope it’ll be plain sailing to happily ever after, but we all know how naive that is. Reality is much harder than the illusion of fantasy, but the difference is that it is real.

We should expect to trip, stumble, and make mistakes along the way, and we might even get hurt too. But we should remember that as much as Yakov was permanently injured in his encounter, he still emerged as Yisrael, the master. It is the human condition to fight and struggle, but we can win.

The Hebrew word for grappling is cognate to the word for dust because the fighter’s feet stir up dust when fighting for leverage and grip – וַיֵּאָבֵק / אבק. The Midrash suggests that the dust kicked up from this epic struggle rose all the way to the Heavenly Throne.

R’ Tzvi Meir Silberberg highlights that the Midrash doesn’t say that the victories go up to Heaven, perhaps because our victories are personal and not always within our control.

It’s important to note that Yakov doesn’t even really win – he holds out for a stalemate while seriously injured. The victory – וַתּוּכָל – is in staying in the fight and not giving up – וַיַּרְא, כִּי לֹא יָכֹל לוֹ. Our biggest tests, if not all of them, are when we are alone. This theme repeats itself with Yosef, home alone with Potiphar’s wife. About to give in to an almost irresistible temptation, he sees his father’s face, reminding him that his family heritage is that he has what it takes to stand alone and not give up. This characteristic is also highlighted in Bilam’s reluctant blessing to the Jewish People – הֶן־עָם לְבָדָד יִשְׁכֹּן.

It’s our lonely struggle that ultimately endures and carries the day.