Challenging Faith: 3 Ways You Must Be Spiritually Shrewd

By Joel Lund 

The Background: You, like me, probably think of the word “shrewd” in a less than flattering way. While these days shrewd may include connotations of being clever or canny, in Middle English “shrewd” described someone evil in nature or character, an evil person, or simply a villain. That’s generally the definition that I locked down regarding “shrewd.” Let’s just say it wasn’t a behavior my parents encouraged me to aspire to. 

Plus, the Old Testament is full of negative examples of shrewd behaviors. See Psalm 83:3, Proverbs 19:25, Jeremiah 4:22 for examples. These also informed my poor view of shrewdness. 

So, it may come as a surprise that Jesus tells his disciples and followers to be shrewd. Maybe that’s why you probably haven’t heard a sermon on Luke 16:8-9, which is the capstone in the Parable of the Dishonest Manager. It’s a bit difficult to wrap your head around. Still, in the age in which we live now it is imperative to not only get comfortable with the value of being shrewd, you must actively nurture becoming as shrewd as you can. 

Be as Shrewd as a Serpent: Before sending out the twelve, Jesus told his disciples to “be as shrewd as serpents and as innocent as doves.” (Matt. 10:16, NASB) Do you find this command a bit difficult to track with? Me, too. But then, how could we not? The universal symbol of peace is a dove, while snakes are considered by most people to be, well, snakes. “You’re a snake!” is not a declaration of affection. 

It helps a great deal to recognize Jesus is employing a simile here. Because we can’t become either a dove or a snake, we’re to behave like them. Shrewdness in this context isn’t to be understood as being deceptive, cunning or villainous, any more than being innocent is to be understood as being unthinking in our acceptance of events or people (gullible). 

Clearly, Jesus was harmless in every way. Pontius Pilate declared him to be an innocent man three times (John 18-19). Still, He also showed shrewdness — wise in the ways of the world — in the way He taught. 

1. MichaelHoudmannputs it this way: “When Jesus told the Twelve to be as wise as serpents and harmless as doves, He laid down a general principle about the technique of kingdom work. As we take the gospel to a hostile world, we must be wise (avoiding the snares set for us), and we must be innocent (serving the Lord blamelessly).” 

We see Jesus do this in the parable mentioned above, found in Luke 16. 

Be Shrewd Like the Dishonest Manager: Jesus tells a crowd of people, certainly including Pharisees and legal experts, a parable about a rich man who is cheated by his operations manager. Having been told by his master that he’d been found to be dishonest and that his accounts were going to be audited, the manager immediately went to debtors of his master and reduced their bills, further defrauding his master. But in so doing, he gained favor with them so he’d have a place to land after destroying his position of importance. Sounds like a snake, doesn’t he? Indeed, he was a villain. 

But Jesus declares:  “And his master praised the unrighteous manager because he had acted shrewdly; for the sons of this age are more shrewd in relation to their own kind than the sons of light. And I say to you, make friends for yourselves by means of the wealth of unrighteousness, so that when it fails, they will receive you into the eternal dwellings.” (Luke 16:8-9 NASB) 

Alexander MacLaren, a Scottish theologian and preacher in the 1800s, points out that even the rich master who was seriously wronged by the dishonest manager commended him for his “clear insight into what was the right thing to do.” The manager was clever. After knocking some of those bills in half, you bet he’d be welcomed by those folks, once he was kicked out by his boss! 

Can you imagine the wide-eyed looks the disciples must have had when Jesus recommended the dishonest manager as a role model? 

So then, how are we to be like this shrewd manager? 

In short, we’re to be gentle without being gullible and generous without becoming victims. We’re to be wise about the world around us, like the Apostle Paul. He knew the legal system of his day, and his preaching was designed specifically for the greatest impact on his audiences. 

But there’s more here, isn’t there? What does Jesus mean when he tells us to make friends for ourselves by means of unrighteous wealth? Huh? 

Be Shrewd By Seizing the Day: Jesus doesn’t commend the rascally manager for his dishonesty but for his shrewd use of the vanishing opportunity before him. His only thought is on the moment. He had to act fast to create a favorable outcome (he hoped!) after he lost his job. He quickly maneuvered his way past a bad outcome of his own devious making. 

How does that apply to us today? 

Reverend Michael Stark says, “Jesus’ commendation is tantamount to stating that sinners are able to seize opportunity to promote wickedness while saints fail to advance the cause of righteousness. Another way of stating the matter is to note that the sons of this age are more proficient at being sinners than the sons of light are at being saints! Underscore that thought in your mind.” 

Unless you have been living under a rock for many years, you’ll have noticed the world has changed. What was once seen as right is now wrong. What was once wrong is now right. Senator Patrick Moynihan spoke of “moral deregulation” back in 1993, by which he meant that society has a limit of bad behavior it can tolerate before it starts to lower its standards. Charles Krauthammer, the legendary columnist, stated that same year the reverse is also true: not only would society normalize what was once seen as deviant, it would also consider deviant what was once seen as normal. 

That sounds a lot like our world today. 

Why then are we to “make friends by means of the wealth of unrighteousness”? Because when it fails — and it will fail — we’ll be received “into the eternal dwellings.” Jesus isn’t saying we’re to become friends with wealth. He’s saying we’re to become friends by means of earthly wealth, to be good stewards of wealth here even with our eyes focused firmly on eternity. 

The crooked manager only looked to the value of each moment and only for his own benefit. His shrewdness, which earned the commendation of his injured master, was praised by Jesus because it was clever, audacious, and resourceful, even if only for the moment and completely self-serving. 

To be the church today means it is time for each member of it to level up. We must seize the day. We must make use of every opportunity to deepen our faith and widen our influence to those around us. We must dedicate ourselves to it with greater enthusiasm and effort than we do with our gym membership, hobbies, habits or any other pursuit. 

What MacLaren said over a century ago is just as true today: The secret of success religiously is precisely the same as the secret of success in ordinary things. 

Whether those ordinary things are shrewd management, wisdom in stewardship of our finances, or how we engage people on social media, we must become more proficient at seizing the opportunities that present themselves to us. Let us be clever, audacious, resourceful and quick to respond, seeking always to be shrewd but innocent, assertive because the time is short, advancing the cause of righteousness until we reach our eternal dwellings. 

Joel is a certified master coach, business strategist, and author. Most importantly, he’s worked with a lot of people just like you. Chat with him. There’s no charge. Schedule here: .