Moshe Rabbeinu's Leadership: "Like herding cats"

May this dvar Torah be in memory of my grandmother of blessed memory, Roslyn Orenstein, who's Yahrzeit is today. Chaya Rashka Leah bat Devorah

The book of Devarim in many ways is Moshe Rabbeinu's greatest legacy. He reviews what he learned from the Jewish people, from their shared time together, and his reflections on the journey to nationhood, and all the vicissitudes, and challenges the journey was fraught with. Right off the bat, in the beginning of this week's parsha, we can see a hint into the treacherous path any leader faces, in addition to the self-awareness it took to be a leader of Moshe Rabbeinu's stature. 

After reaffirming Hashem's covenant with the forefathers and His promise to bequeath us the land, Moshe states: 

"Thereupon I said to you, “I cannot bear the burden of you by myself.

The LORD your God has multiplied you until you are today as numerous as the stars in the sky.—"

I would like to ask, why it is here that Moshe compares the Jewish people to the "stars of the sky?" Two metaphors, or rather, similes, are used to portray the multitudes of the Jewish people, the sands on the ocean shore, and the stars of the sky. 

It would seem to me here that the "stars of the sky" is used to exemplify the individualism of the Jewish people, one Jew, two opinions; the sand is one body, one unit, the stars, each unique, shining and emanating their own light. 

Never do we see in a more pronounced way the capacity of a leader to transform the nation he led than in the annals of the Jewish people, Moshe, a young prince, leaving the royal grounds to see the suffering of his people, breathing life into their hopes for freedom, standing down the greatest monarch of the time, bringing the Jews into an arid dessert, giving them the Torah, and leading them, day in and day out, from an unruly, incohesive nation of former slaves to a nation, unified as one, ready to inherit their ancestral lands. 

The one caveat, though, is that Moshe who gave the Jewish people their individualism, who taught them the meaning of time in the very first commandment given to the people as a whole, i.e. Rosh Chodesh, could - at a later stage - no longer deal with the multiplicity of opinions, the 600,000 voices each tugging in a different direction. 

I think that this message is said ever so poignantly when Moshe prays for a new leader who will be like God in that he will know the desires of each and every person: "O God, the God of the spirits of all flesh." That's exactly what Moshe seeks, a leader, as Rashi explains, who will understand the unique contours of every spirit, who will be able to make and every Jew shine. 

Perhaps not so connected, but I remember learning in my Bachelors of Business Administration, that very often the entrepreneur who spearheads a new company, who founds it from the very get-go, is not the right leader to see it through when it matures. Often, the entrepreneur, or venture capitalist, isn't the right person to take the reins and become the CEO, when a company enters a new stage of maturity, goes public, or expands beyond a certain level. 

It would seem that a little of that rings true in the transition from Moshe Rabbeinu to Yehoshua, or Joshua, who would become a leader of his own, having grown up in Moshe's tent, only to then open the doors for a new generation: הרחיבי את אוהלייך.