"….Said Rabbi Nappaha: 'I will tell you a parable. To what can it be compared? To a man with two wives, one young, one old. The young one pulls out his white hairs, while the old one pulls out his black hairs, and thus he becomes bold from either side!'" (BT Baba Kama 60b)

In the Talmud, Rav Ammi and Rav Assi, two sages often quoted together, are studying with Rabbi Yizhak Nappaha. Each student wants his mentor to teach the material that he enjoys most: One asks for legend (midrash), the other for law (halakhah). Rabbi Yizhak is caught in a bind. When he start to teach midrash, one student interrupts and asks his teacher for law. But when Rabbi Yizhak switches to law, the other student prevents him from continuing, for he prefers legend.

Being a master teacher, Rabbi Yizhak resorts to the use of a parable to explain his predicament: A man with two wives, one young and one old, would have one of them wanting him to look more youthful and the other desiring a more mature husband. Although each wife pulls out only some of his hair, the result is that the man is left "bald from both sides." (In the subsequent passage, Rabbi Yizhak demonstrates his outstanding teaching abilities, by finding one biblical verse that serves the purpose of both a midrash and a law, thus satisfying both students.)

The expression "bald from either side" is used in modern Hebrew
to suggest a "no-win" or "Catch-22" situation.

 

From: Swimming in the Sea of Talmud: Lessons for Everyday Living, by Michael Katz & Gershon Schwartz (JPS, 1998)