To answer this we need to add another layer to the story—that of honor and shame. A number of recent commentators have pointed out that the manager’s wasteful actions not only brought shame upon himself but also upon the rich man (who would be viewed as weak and unable to control his employee as well as his business). If we look at the manager’s discounting of the bills from this perspective, it would be regarded by the debtors as reflecting the rich man’s wishes since the manager served as his representative and agent. This would generate a large amount of goodwill toward his master and restore the honor that had been previously lost. In the Mediterranean culture of the first century, this would have been even more important than the amount by which the bills were reduced.
What we end up with then is a win-win-win situation. The debtors win because their bill is reduced. The manager wins because he had won the favor of many potential employers. The rich man wins because his honor has been restored.

The takeaway from the story for Jesus is the manager’s shrewdness—not his stealing. What Christ is doing is no different than what preachers do when they exemplify the unity displayed by the people who were building the tower of Babel (Genesis 11:6). They’re not condoning the wicked intent of these people (compare v. 4 with 9:7, 10:32), but pointing out what can be accomplished when people commit to working together. There’s no moral dilemma here.
The manager was in an extremely tight situation when he was fired. He had little time, opportunity, or influence. Yet he used what he had to secure his future. This is exactly what Jesus says disciples are to do (Luke 16:9).
We also have a limited amount of time, resources, and opportunity. We should use these for the kingdom of God and by doing so we’ll secure our future. Christ is not teaching that we can buy our way into heaven—He’s charging us not to be wasteful stewards as the business manager initially was.
This is a much needed lesson because many are tempted to simply say they trust in God to provide and somehow think that this frees them from any personal management responsibilities. While trusting in God is critically important and never to be discounted, it doesn’t preclude our duty to work hard (and smart) to use what God has given us in the best ways possible. You may have heard the saying, “Pray as though everything depended upon God; work as though everything depended upon you.” I think that’s exactly what this parable is teaching.
In conclusion, this is certainly a story that makes us think about its meaning and application. In that way, it reflects the challenge of living as generous disciples and using our possessions for the kingdom of God.