"Now therefore give me this mountain, whereof the LORD spake in that day; for thou heardest in that day how the Anakim were there, and that the cities were great and fenced: if so be the LORD will be with me, then I shall be able to drive them out, as the LORD said." (Joshua 14:12)
David Woods writes in "God's Word for Today":

The most admirable aspect of Caleb's bold request to receive the inheritance God had promised was not his age, his perseverance for forty-five long years in the wilderness, or his courageous stand when the rest of the nation wanted to return to Egypt. Rather, Caleb's confident attitude is seen most now, having that past, asking for one of the most difficult areas of Israel in which he might settle.
The land Caleb wanted was mountainous. It was filled with the Anakim, the giants that scared the ten spies so many years before, and the remnants of which settled in Philistine territory.

Discussion: When you have your choice of challenges, do you choose the most difficult or the easiest?
Source: Biblical Family Values, Adult Teacher's Insights, page 24.