Upon crossing into enemy territory, he and another spy, later to become his greatest ally, fellow leader, and lifelong friend, saw nothing but the bounty they had been promised. The residents were healthy and strong, the land fertile and rich, the cattle well-fed, and the harvest was beyond anything they had seen before, seeming like something from a starving child's dreamworld.
He could taste the victory, and feel himself building a home where he could settle with his family, and watch his children grow, bearing grandchildren who would play in the green grass and fertile fields. Yet as soon as the warmth and hope of this vision filled his heart, it was torn away by fear, fear from his fellow spies.
Although both he and the men had been freed from oppression, the other men still lived as slaves. Upon seeing the riches of the land, they could feel the slavemaster whip their backs, driving them to produce for the comfort of these wealthy few, and they fled, convincing their people to forgo the blessings of a promised land for the imagined safety of a nomadic existence.
The majority got their wish, and were sentenced to forty years of desert living, while just over the horizon, just over that river to the west, the reason for their freedom lay out of reach.
Not till 40 years later, after that fearful band of spies had been buried in the sands, did Caleb and his new commander Joshua, enter that Promised Land. At 80, he was just as vigorous as the former spy of his middle age. For the next 5 years he fought alongside his friend Joshua as they conquered the land of milk and honey, then at the ripe old age of 85 he claimed his inheritance with one final battle against the giants of the land.
St. Ambrose commenting on the faith of Caleb (and the fear of the other spies) says:
"he preferred glory to safety; the worse part safety to virtue. The Divine judgment approved those who thought virtue was above what is useful while it condemned those who preferred what seemed more in accordance with safety than with what is virtuous."
A commentator summarizes this with the following exhortation:
"God rewards those who prefer the virtue of obedience over the safety of inaction."
Fear may be an indicator toward obedience. God does not call us to comfort but a cross. Fear is the natural reaction to our own crucifixion, yet on the other side is the Promised Land.
What is risky about the virtuous life? What scares you about obedience?