Jesus was not saying that private property is evil, nor that we must all empty our bank accounts overnight. As we saw God does not feel guilty about being the wealthiest person in the universe, and neither should we feel guilty for the many blessings that he has given us. So what does he mean?
Think of the pioneers, moving west, opening up the territory that made the United States great. These families on the frontier traveled in difficult and dangerous terrain. Often their wagons and oxen could make no further progress on the hazardous trails and daunting mountain passes because of their heavy loads. They could not afford to lose their tools, their food, their seed and tree plantings, so they had to undergo the heartache of jettisoning their heirloom furniture, discarding precious wedding presents at the roadside.
These were the true pioneers. Those who could not part with the past did not leave their homes - or if they left, they turned back or perished on the way. It was not possessions that were evil; it was the orientation toward the past rather than the future that was the snare. A wagon full of treasure that would contribute toward the future glory of fresh settlements was to be prized rather than discarded, but treasures rooted in nostalgia, while not evil in themselves, on occasion had to be released.
To seek first the Kingdom of God is to have a one track mind. Lots of things have to be given up to get to the end of the road. Yet Paul could say that he counted loss as pure joy. There was joy in Jesus' parables. The man who found treasure in the field had to sell everything in order to buy that field, but we are told that it was "in his joy [that] he goes and sells all that he has and buys the field" (Mt 13:44). That's how the west was won. Not won for the American Dream, for that is part of what we must be prepared to lose! Won for the Gospel by men and women who pay the price to buy the treasure.