And it turns out, even Moses, the greatest prophet of them all, knew what that was like.

Devarim Rabbah, a collection of rabbinic teachings on the Book of Deuteronomy, explores this very dynamic. It opens with Moses’s plea, "I pleaded with the Lord" (Deuteronomy 3:23). And then it poses a question: Why was Moses, who had such a close relationship with God, reduced to pleading?

The Midrash, in its beautiful, layered way, offers several answers, drawing on the wisdom of Proverbs. "A poor person speaks with pleas, and a wealthy one responds harshly" (Proverbs 18:23). Rabbi Tanhuma interprets this to mean that Moses, in this moment, is the "poor person," humbling himself before the "wealthy One of the world," namely, God. And God, in turn, responds sternly, as the verse states: "Do not continue speaking to Me" (Deuteronomy 3:26). Ouch.

But the Midrash doesn't stop there. Rabbi Yoḥanan offers another perspective. He suggests that the "poor person" represents the prophets of Israel, who approach God with taḥanunim (pleas for mercy). In contrast, the "wealthy one" represents the prophets of other nations. According to Rabbi Yoḥanan, even the most righteous among the nations, like Job, came with tokhaḥot (reproaches and arguments), not pleas. As it says in Job 23:4, "I would organize my case before Him and fill my mouth with arguments." The prophets of Israel, the ones closest to God, approach Him with humility and a plea for grace. Even the mightiest among them, like Moses and Isaiah, only came with pleas. Isaiah says, "Lord, be gracious to us [ḥanenu] ; we have longed for You" (Isaiah 33:2).

The Midrash then uses a powerful analogy to illustrate Moses's situation. Imagine a noblewoman who has borne a child to the king. As long as her son is alive, she can enter the palace freely, without question. But when her son dies, she must beg for entry.

Similarly, as long as the generation that left Egypt was alive in the wilderness, Moses could approach God with a certain boldness. "Lord, why will Your wrath be enflamed against Your people?" (Exodus 32:11) he'd say. "Please pardon the iniquity of this people…" (Numbers 14:19). But when that generation died in the wilderness, Moses found himself pleading to enter the Land of Israel. "I pleaded," he says, a poignant echo of his diminished standing.

What does this teach us? Perhaps it's that even the most righteous among us must approach God with humility. That even after a lifetime of service, we can't take our relationship with the Divine for granted. And maybe, just maybe, that the act of pleading itself—the vulnerability, the acknowledgement of our own limitations—is a crucial part of the spiritual journey. Because sometimes, the greatest strength comes not from demanding, but from humbly asking.