It was only studying this passage just recently that I think I might be starting to get Jesus' point - and it's right in the middle, trying to get our full attention: “With man this is impossible, but not with God; all things are possible with God.” Whether its wealth, or possessions, or family (I'm reading God's command of Abraham to sacrifice Isaac in Genesis 22:1-18 differently now), or land that we're holding on to for our security, we're doomed. God want us to cling to and put our full faith in Him, the source of anything we could possibly need, not the blessings that He so richly gives us and the rest of the world.
God isn't asking us to give up what we need in order to be utterly barren. God is asking us to let go of what we think we need in order that He can fully bless us (to be a blessing) through our faith in Him.
In light of all this, the question I'm pondering is: "What am I holding onto that might be getting in God's way?"