The ancient rabbis certainly did. And they wrestled with this tension in some fascinating ways. Let's dive into a passage from Kohelet Rabbah, a collection of rabbinic interpretations of the Book of Ecclesiastes, and see what wisdom we can unearth.

The verse in question is Ecclesiastes 7:16: "Do not be overly righteous, and do not be exceedingly wise; why should you be destroyed?" Seems a little strange, right? Shouldn't we strive for righteousness? Well, the rabbis take this verse as a warning against a specific kind of self-righteousness – one that presumes to be more righteous than God Himself.

The text uses the story of King Saul to illustrate this point. We find in 1 Samuel 15:5 that "Saul came to the city of Amalek [and lay in wait [vayarev] in the valley]". Rabbi Huna and Rabbi Benaya offer a powerful interpretation: that vayarev – usually translated as "lay in wait" – can also mean "to argue" or "to deliberate." They suggest Saul was essentially arguing with God! He was questioning God's command to utterly destroy the Amalekites: "Go and smite Amalek…[put to death both men and women, infant and suckling babes, ox and sheep, camel and donkey" (1 Samuel 15:3).

Saul, in his human compassion, wondered: "If the men sinned, what sin did the women commit? What sin did the children commit? What sin did the cattle, the ox, and the donkey commit?" It's a valid question, right? We can understand his hesitation. But according to this midrash, a Divine Voice emerged, essentially saying, "Do not be overly righteous; [do not be] more [righteous] than your Creator."

The rabbis offer another interpretation too. They say Saul also questioned the ritual of the beheaded calf (eglah arufah), described in Deuteronomy 21:4. This ritual was performed when a person was found murdered between two cities and the killer was unknown. The elders of the nearest city would perform this ritual, in which a calf is beheaded. Saul was uncomfortable with this, arguing that a calf shouldn't be killed because of a human sin. Again, he's demonstrating compassion. But the Divine Voice rebukes him: "Do not be overly righteous."

So what’s the takeaway here? Are the rabbis advocating for unrighteousness? Of course not! The point, it seems, is about humility and trust. There are times when we simply cannot fully grasp the Divine plan. To presume our understanding is superior, to allow our compassion to override Divine instruction, is a form of arrogance.

Rabbi Shimon ben Lakish takes it a step further. He says that "Anyone who becomes compassionate when he should be cruel will ultimately become cruel when he should be compassionate." He points to the tragic event in 1 Samuel 22:19, where Saul, having spared the Amalekites, later ordered the slaughter of the priests of Nov. Was this not like the descendants of Amalek, he asks? A chilling consequence of misplaced compassion.

And the Rabbis add that "Anyone who becomes compassionate when he should be cruel, ultimately, the attribute of justice will harm him," leading to his own tragic end: "Saul and his three sons died" (1 Samuel 31:6).

This isn't an easy lesson. It requires us to hold seemingly contradictory ideas in tension: compassion and justice, understanding and trust. We must strive for righteousness, yes, but always with humility, acknowledging the limits of our own understanding. Perhaps, the greatest wisdom lies in knowing that we don’t have all the answers. And maybe, just maybe, that's enough.