And nowhere is it more poignant than in the story of Moses, right before his passing.

Imagine this: Moses, the greatest prophet, standing at the edge of the Promised Land, knowing he won't cross over. His heart, undoubtedly heavy, is filled with concern for the people he's led for forty long years. According to Sifrei Devarim, he turns to the Holy One, Blessed be He, with a heartfelt plea. "L-rd of the universe," he says, in essence, "I'm leaving this world. Show me a trustworthy person, someone to guide them in peace." He wants someone who will "go out before them and who will come in before them, and who will take them out and who will bring them back," just as the Torah states in Bamidbar (Numbers) 29:17. Moses doesn't want the "congregation of the L-rd" to be "as sheep without a shepherd."

Isn't that a beautiful, human image? Moses, the towering figure, worried about his flock.

This plea echoes in the tradition. The Song of Songs (1:7) asks, "Tell me, O You whom my soul loves: Where will You graze (Your flock)? Where will you lay (them down) in the afternoon? For why should I be like (a woman) veiled (in mourning) among the flocks of Your neighbors?" It’s a desperate cry for direction, a fear of being lost and vulnerable.

And what is G-d's response? It's… unexpected. Instead of naming a successor outright, He says (Ibid. 8), "If you do not know, O fairest of the women (i.e., "greatest of the prophets"), go out in the footsteps of the sheep." What does this mean? The text interprets this as: see what I am destined to do with them in the future. In other words, look to the patterns of history, to the way I've guided them before.

Because, sadly, the path ahead won't always be easy. The text goes on to say that Israel will pass through four exiles—"without a shepherd, without a prophet, without a sage." Times of immense hardship and spiritual desolation. It's a stark reminder that leadership isn't always readily available.

This idea finds further resonance in II Chronicles 18:16, which describes a vision of Israel "scattered on the mountains like sheep that have no shepherd" during the days of Achav. A time of immense spiritual crisis.

So what are we to make of this? Is it a pessimistic outlook? Perhaps. But I think there’s a deeper message here. While strong leadership is vital, it’s not always guaranteed. We, as individuals and as a community, need to cultivate our own inner compass, to learn from the past, to seek guidance from tradition, and to trust that even in the darkest of times, the Divine presence is still there, subtly guiding our steps. It's a call to develop our own spiritual resilience and to find our own way, even when the shepherd seems absent. And maybe, just maybe, to become shepherds ourselves.