Here is the question my rav, Yossi Gordon, posed about this week's reading, in which Moshe sends out scouts to do reconnaissance on the Land of Israel ahead of the upcoming entry. How could Moshe ask, "Is the country in which they dwell [i.e. the Canaanites] good or bad?" (Numbers 13:19).
Surely Moshe of all people knows that God is sending them toward a good land, flowing with milk and honey. So what's the meaning of this part of the spies' charge?
Two possibilities. One is that Moshe already knows what the scouts will say. He gives them the illusion of choice, so they'll feel that the answer he wants them to get is really theirs. It would be like an exercise in decision-making, a big choice made in safe conditions to build self-confidence.
Only it turns out they didn't come back and say what a good land it was! Or, to be precise, ten of the twelve came back with a negative assessment of the land.
So the other possibility is that Moshe gave them a chance to fail, to come back with the wrong answer. Which they did.
You can argue with Moshe's (and God's) strategy here. A lot of damage happened as a result of this mission -- a whole generation ended up lost. God made the people wander for forty years, until the fearful generation passed and a new more courageous Israelite people came of age. I don't want to minimize that.
But maybe Moshe and God looked at it differently. Already, the people were restless, impatient, impetuous. They were in no condition just to follow a command to enter the land. Suppose they entered right away, and then had to face big choices. What if it all went wrong and could never be made right?
So Moshe and God decide to take the measure of the people. Are they ready to see that the land is good? If they are, then the mission will be successful -- entering the land, living by the Torah. And everything would be all that much better because the triumphs, military and community-building and moral, would really belong to the people.
If the scouts would fail, then at least the disaster to follow would take place in the safety of the desert, under God's more immediate protection.
That's how it happened. It looks like the battle was lost. But perhaps this was had to happen to win the war (much) later, to enter the land successfully at last.
So it is with forks in the road, or with questions of maturity. The road isn't always smooth. Sometimes with our children, our students, our teams and groups, we have to test and see if the time is right. If the people are ready. By giving a real choice, knowing that failure now will be an option. The opposite of success now isn't necessarily failure forever. Rather, it's a setback for now, even a long now. A setback played out in a safe place, under the care and concern of someone Moshe-like. Willing to hang in with difficulties and difficult people, willing to teach, for the long haul.