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Why did Yaakov want to go out to the beis medrash when he was already learning with a malach in the womb? The shiur challenges Rav Chaim Volozhiner's answer (that Yaakov wanted to separate from Esav) by showing Yaakov actually wanted to bring Esav with him. An eight-year-old's insight provides the real answer: Yaakov preferred learning independently over being spoon-fed by a malach—true Torah (תורה) acquisition requires personal struggle.
The shiur opens with the well-known Midrash on Parshas Toldos describing how the embryos struggled in Rivka's womb—when she passed a beis medrash, Yaakov wanted to go out, and when she passed places of idolatry, Esav wanted to go out. Rabbi Zweig addresses a famous question attributed to Rav Chaim Volozhiner in the Nefesh HaChaim: if Yaakov was already learning Torah (תורה) with a malach inside the womb, why would he want to leave that elevated form of Torah study to go to a regular beis medrash? The answer often given is that Yaakov wanted to separate from Esav because of the prohibition of "al tischabair l'rasha"—one should not attach himself to a wicked person—even if that means giving up learning with a malach. Rabbi Zweig forcefully rejects this explanation and argues it is actually a proof to the opposite. If Yaakov truly wanted to separate from Esav, the solution would be simple: when they came to a place of idolatry and Esav wanted to go out, Yaakov should have let him go. Then Yaakov could either remain inside learning with the malach by himself, or go out to the beis medrash on his own. The very fact that Yaakov struggled with Esav and held onto him demonstrates that Yaakov did not want to separate from his brother.
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Parshas Toldos, Bereishis 25:22 (Midrash on the struggle in Rivkah's womb)
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