Maybe you'd messed up before, and the consequences stung. It's a very human feeling, that hesitation. And guess what? Even Moses, Moshe Rabbenu himself, felt it too.

Our story comes from Devarim Rabbah, a compilation of rabbinic interpretations on the Book of Deuteronomy. It opens with a fascinating glimpse into Moses's mindset as he prepares to review the Torah with the Israelites.

Rabbi Simon tells us that when God commanded Moses to review the Torah with the people, Moses initially hesitated. Why? He didn't want to rebuke them. It sounds strange, doesn't it? Why wouldn't the great leader, the lawgiver, correct his people?

Rabbi Simon uses a beautiful parable to explain. Imagine a student walking with his teacher who spots a glowing ember. Thinking it's a precious gem, he eagerly grabs it, only to be burned. Later, he sees a real gem but, scarred by his previous experience, mistakes it for another hot ember and hesitates to touch it. His teacher then has to reassure him, “Take it, it’s a gem!”

Moses, according to this midrash, was that student. He remembered the incident when he struck the rock to bring forth water, a moment where he addressed the Israelites as "defiant ones" (Numbers 20:10). The midrash implies that this moment, this perceived harshness, led to his punishment – his inability to enter the Promised Land.

So, Moses reasoned, “Because I said to them, ‘Hear, now, defiant ones,’ I received my punishment because of them… will I now come to rebuke them?” He feared that any further rebuke would only bring more hardship upon himself and the people.

Think about that for a moment. Moses, despite his immense stature, was deeply affected by his past actions. He carried the weight of responsibility, the knowledge that his words had consequences.

But God, in His infinite wisdom, understands Moses's fear. The midrash concludes with God reassuring Moses: "Fear not." God knew that the Israelites needed guidance, even if it meant revisiting past mistakes. Moses's role was to teach and lead, and he shouldn't let fear paralyze him.

What can we learn from this? Perhaps it's about the delicate balance between holding people accountable and offering them grace. It's about understanding that even those in positions of authority struggle with self-doubt and the fear of repeating past mistakes. And it's about the importance of divine reassurance, the idea that even when we hesitate, we are not alone in our efforts to guide and teach.