The steward was about to lose his living: "my lord taketh away from me the stewardship." He asked himself what to do and ruled out two options: "I cannot dig; to beg I am ashamed." Gill puts the question in plain terms: "what shall I do for a maintenance? how shall I live?" Barnes says "I cannot dig" may mean his work had not fitted him for farm labor, or that he was "unwilling to stoop to so low an employment," and that about begging, "He was too proud for that." Matthew Henry notes that only now, facing the loss, "he began to consider, What shall I do?"

The steward answered his own question: "I am resolved what to do, that, when I am put out of the stewardship, they may receive me into their houses" (Luke 16:4). He called his lord's debtors one by one and had them rewrite their bills for less (Luke 16:5-7). Then "the lord commended the unjust steward, because he had done wisely" (Luke 16:8). Barnes observes that "one sin leads on to another": the steward who had wasted goods now used dishonesty to secure his future.

To "dig" meant hard farm work. Barnes takes it of working in agriculture, and Gill notes that the Arabic version renders it "plough." Begging was the other option the steward named. Gill, who reads the steward as a picture of the Pharisees, points to the Pharisee's prayer in Luke 18:11 and notes "you will not find one petition in it," as if to say such men were above asking for anything. The steward's word for his position, oikonomia, means management or administration of another's household.

Jesus does not hold up the steward's honesty as an example. Luke calls him "the unjust steward" (Luke 16:8). What Jesus points to is his foresight: "the children of this world are in their generation wiser than the children of light" (Luke 16:8). The steward thought hard about where he would live after he lost his job. Jesus calls His disciples to think just as seriously about "everlasting habitations" (Luke 16:9).

Matthew Henry's Concise Commentary captures the contrast: "Worldly men, in the choice of their object, are foolish; but in their activity, and perseverance, they are often wiser than believers." The rich fool asked the same question, "What shall I do?" (Luke 12:17), but planned only for this life. Jesus wants His people to ask it with eternity in view.