This proverb from Jesus is a commentary or a side note on a parable he just told, about "the dishonest manager". The ESV & HCSB title the story that way, but the NLT & NIV call it "the shrewd manager". Eugene Peterson has, "the crooked manager".
Some Bible experts say that this is the hardest parable in Luke, to interpret. There is difficulty in seeing what Jesus point was, with possibly asking us to emulate a dishonest person. But, as is often the case, the context helps us understand the text.
The context is a story about a person and their money or resources. It is the story of allocation or investing assets or commodities. It is a story of how to manage or do beneficial process in a financial crisis.
In the story, the manager did good business right before he lost his position. He was a seller or a trader, who managed assets: buying, selling, and trading; for his boss. The boss decided that the manager was doing poorly, so he dismissed him.
But before the manager packed up and handed things back to his boss, he made a number of finishing deals with the accounts (people) he dealt with, for his boss. He lowered the amount that each owed and got each account or deal closed and settled.
We do not know if these were, "I am going out of business", discounts; in order to not leave loose ends and make his boss happy; or if the manager himself paid the difference, blessing these customers and his boss. Either way, his boss did compliment him on the way out; and more importantly, Jesus complimented him.
So, what is this all about, and how does it apply to Christians today? It is about investing or generously giving money or commodities to people who are in need. Jesus is saying that just as the boss in the story praised him for what he did for his customers, you will be praised by people who you generously give to, who are in need; in this life and in heaven.
Diametrically opposed to this generous lifestyle that Jesus teaches, were the Pharisees, who loved money. And Jesus says that we can not love God, serve God; and love or serve money. Money is meant to serve people who love and serve God.
Money is a great tool to bless people, because people who do not have money need money to eat and live. God blesses us with money to enjoy our lives and to give it away to people who are in need. How we handle our money is a barometer of our spiritual maturity and readiness to receive opportunity and responsibilities in the kingdom.
Do we love God and love people, or do we love money? If we hoard money, if we are not generous to those in need, and if we see money and commodities that we have as only for us; then we are not walking in the generous love-way of Christ. And unless we change direction, we will arrive at where we are headed.
How we handle dollars or our extra stuff are the little things that are very important in Jesus eyes, because they give us a reading on how our hearts are. Generous hearted people can be given spiritual promotion or kingdom duties. Generous hearts are identified through generosity in dollars and sense.