And the Rabbis of the Midrash, in Kohelet Rabbah, take this even further, using stories and interpretations to unpack the weight of those feelings.

One particularly stark verse they dissect is Ecclesiastes 6:3: “If a man begets one hundred, and lives many years, and the days of his years are many, but his soul is not sated from the good, and he did not have a burial; I say, a stillborn is better than he.” A pretty harsh assessment. So, who is this tragic figure?

The Rabbis offer a few interpretations, the first pointing to Cain. Yes, that Cain, the one who killed his brother Abel. Kohelet Rabbah reads into the verse, suggesting that Cain fathered a hundred sons and lived a long life, yet his soul remained unsatisfied. He was never sated by earthly goods, and ultimately, he didn't even receive a proper burial; the flood swept him away. As it says in Genesis 7:23, God "obliterated all the yekum" from the face of the earth.

Now, yekum is an interesting word. What does it mean here? Rabbi Bon suggests it refers to "sustainers" (okuminei) – those who develop and sustain the world, in other words, people. Rabbi Elazar says yekum refers to possessions, those things that bolster a person's standing, that help them "stand" (lakum). But Rabbi Shmuel offers a particularly chilling interpretation: yekum is Cain himself! Remember, the Torah says "Cain arose [vayakom] against Abel his brother, and killed him" (Genesis 4:8). So, this Cain, burdened by guilt and ultimately erased by the flood, is worse off than a stillborn – in this case, Abel. Even though Abel died young, he was spared Cain’s suffering and ignominious end.

It's a powerful image: a life of outward success masking an inner emptiness, culminating in complete obliteration.

But the Rabbis don’t stop there. They offer another example: Ahab, the infamous king of Israel. The text says, "If a man begets one hundred…” – this, the Rabbis say, is Ahab, who fathered a hundred sons. Wait, didn't II Kings 10:1 say he only had seventy sons in Samaria? Rabbi Hoshaya clarifies, saying Ahab had seventy sons in Samaria and seventy in Yizre'el – more than a hundred in total! And these sons lived in luxury, each owning multiple palaces for different seasons, as alluded to in Amos 3:15: “I will smite the winter house with the summer house.” Rabbi Yehuda ben Rabbi Simon even suggests they each had four houses – two for summer, two for winter! Others say six.

Yet, despite his power and his sons' extravagant lifestyles, Ahab, too, was unsatisfied. "His soul was not sated from the good," the Rabbis interpret. And, famously, Ahab also suffered an unceremonious end. Remember the story of Naboth's vineyard? As we read in I Kings 21:19, because of Ahab's injustice, God declared that dogs would lick his blood in the same place they licked Naboth's. So, Ahab, like Cain, is deemed worse off than a stillborn, even “the stillborn of a prostitute,” who at least receives a burial.

What are we to make of these interpretations? Are they simply cautionary tales about the dangers of wealth and power? Perhaps. But they also speak to something deeper: the importance of meaning. It's not enough to simply exist, to accumulate possessions, or even to have children. We need to find something that truly satisfies our souls, something that gives our lives purpose and value. Otherwise, we risk becoming like Cain or Ahab – figures of outward success but inner emptiness, ultimately consumed by their own unfulfilled desires. And that, the Rabbis suggest, is a fate worse than never having lived at all.