Shrewd or Wise?

The chief priests asked exactly the right question but for exactly the wrong reason. Shrewdness asks "what answer protects me." Wisdom asks "what answer is true."

Aug 04, 2026

He was a canny businessman. He took real pleasure in knowing he had gotten the better of his associates in deals, negotiations, and life. He seemed to know just when to strike and just the right words to say to get his way and get ahead.

And he was all alone.

His great ability to shrewdly scheme his way to financial success did not translate into his relationships, because everyone around him felt they were always being conned, manipulated, or cheated. No one enjoys feeling that way. Eventually his business associates figured it out as well, and his short-lived success crumbled.

He was shrewd. But he was not wise.

I bet you have known people like this. Always calculating their words and actions to manipulate the situation to their advantage. This is a genuinely useful ability in business and negotiations. But untempered by love and wisdom, it feeds the deepest darkness of a person’s soul. And it always leads to isolation and loneliness, because no one wants to be in a relationship where they feel like the object of a con.

“By what authority are you doing these things, and who gave you this authority?”

The chief priests and elders who confront Jesus in today’s Gospel are exactly this kind of people. They ask exactly the right question. But they ask it for exactly the wrong reason. And the Lord, with a wisdom that cannot be outmaneuvered, exposes the difference.

As we continue in the Dormition Fast, which began on August 1st and prepares us for the great Feast of the Dormition of the Theotokos on August 15th, this season invites us to step back from the calculating, self-interested way of navigating life and allow the Faith to form something deeper in us. The timing is appropriate.

Wisdom over shrewdness is exactly the lesson this season is designed to teach.

At that time, when Jesus entered the temple, the chief priests and the elders of the people came up to him as he was teaching, and said, “By what authority are you doing these things, and who gave you this authority?” Jesus answered them, “I also will ask you a question; and if you tell me the answer, then I also will tell you by what authority I do these things. The baptism of John, whence was it? From heaven or from men?” And they argued with one another, “If we say, ‘From heaven,’ he will say to us, ‘Why then did you not believe him?’ But if we say, ‘From men,’ we are afraid of the multitude; for all hold that John was a prophet.” So they answered Jesus, “We do not know.” And he said to them, “Neither will I tell you by what authority I do these things.”

The chief priests and elders were skilled survivors. Years of navigating Roman occupation had honed in them a particular instinct, always looking for the angle, always calculating the narrow path through a dangerous situation. They were shaped by a survival mentality that had become their primary way of seeing everything and everyone.

And now they confront their promised Messiah. And because of this narrow focus on survival and self-interest, they miss the Abundant Life standing directly in front of them.

What Can We Take From This?

First, shrewdness and wisdom are not the same thing, and only one of them is perfected in love.

The priests and elders ask a genuinely important question. “By what authority are you doing these things?” This actually matters. The authority of the Lord is at the very center of everything He has been teaching and doing. They have stumbled onto exactly the right question.

But they are not asking because they want the answer. They are asking to trap Him.

Their shrewdness is calculating, not curious. Tactical, not truth-seeking. They already know what they want from this exchange, and it is not the truth.

Shrewdness can be practiced by very evil men. The ability to read a room, anticipate an opponent’s move, and position oneself advantageously is a morally neutral skill. History is full of brilliant strategists who were also terrible human beings. The shrewdness itself is not the problem.

The problem is shrewdness without love.

Without the orientation toward truth and toward the good of others that transforms a calculating mind into a genuinely wise one. Wisdom is always perfected in love and service. Shrewdness, unchecked by love, curdles into manipulation. And manipulation always produces the loneliness of the businessman in my opening story, a person surrounded by potential marks rather than actual friends.

Next, the Lord uses wisdom to expose their shrewdness and open a door they cannot see.

“The baptism of John, whence was it? From heaven or from men?”

This is not a clever dodge. This is a mirror held up to their true motivations.

The Lord gives them a question that has exactly the same structure as their own, a question whose answer reveals something essential about authority and belief, and He watches them reason their way around it rather than through it.

They do not ask “What is the right answer?” They ask “Which answer protects us?”

If we say from heaven, we are caught. If we say from men, the crowd will turn on us.

So they say they do not know, which is the answer of a person who has decided that being safe is more important than being honest.

And in that moment of choosing safety over honesty, they close the door themselves. The Lord does not trap them. They trap themselves.

But notice what He is actually doing. The question about St. John’s baptism is an invitation. If they had stopped calculating and started seeking, the answer would have led them exactly to the authority they claim to be asking about. St. John pointed to Jesus. If his baptism was from heaven, then the One he baptized and proclaimed is the answer to their question. The door is right there, if only they could stop being shrewd long enough to walk through it.

This is what the Faith does in us when it is working as it should. It forms in us the character of Christ, which includes the wisdom to discern our own motives and redirect them toward truth rather than toward self-protection.

Finally, the circumstances of our lives will form us in one of two ways, toward deeper self-interest or toward deeper wisdom, and the disciplines of the Faith determine which.

“What have the circumstances of your life shaped in your own soul?”

The priests and elders had been shaped by decades of surviving under occupation. That shaping was real and understandable. But they had allowed it to become their primary lens for everything, including their encounter with the Lord. The survival instinct that had served them in one context had become a prison in another.

Our circumstances form us constantly.

Financial pressure teaches us either generosity or hoarding. Relational betrayal teaches us either wisdom or paranoia. Professional competition teaches us either excellence or manipulation. The question is not whether we will be formed by what happens to us. The question is whether we are submitting that formation to the discipline of the Faith so that it moves us toward the character of Christ rather than toward a more sophisticated version of self-interest.

This is why the Dormition Fast matters. These periods of intentional fasting and prayer are not primarily about what we give up. They are about interrupting the patterns that have formed in us without our noticing and submitting them to something higher. They are the Orthodox practice of asking what the circumstances of our lives have shaped in us and bringing whatever the answer is to God for healing and reorientation.

Wisdom is always better than shrewdness. And wisdom only grows in the soil of love, prayer, and honest self-knowledge.

The Seven Holy Youths of Ephesus

Today we commemorate the Seven Holy Youths of Ephesus, also known as the Seven Sleepers, young Christian men who fled persecution under the Emperor Decius around 250 AD and hid in a cave near Ephesus. They fell asleep in the Lord and were miraculously preserved, awakening nearly two centuries later during the reign of the Emperor Theodosius II, when the resurrection of the dead was being debated. Their awakening served as a living sign confirming the truth of the resurrection and silencing the doubters.

These young men made the opposite choice from the chief priests and elders. When confronted with a choice between survival through compromise and faithfulness through risk, they chose faithfulness. They were not shrewd about their safety. They were wise about what actually mattered. And their wisdom, held in the cave of patient endurance, became a witness that outlasted the emperor who had threatened them and the generation that had doubted the resurrection.

Their hymn says they “scorned all things in the world as corrupted and found the gifts that nothing ever corrupts.” This is wisdom perfectly expressed. They saw through the calculating survival logic of their age to the eternal reality underneath it.

Your Response Today

Today, take a few minutes to honestly examine what the circumstances of your life have been forming in you.

Do you tend to see others as potential marks to further your desires, or as icons of God to be honored and served? Do you approach difficult situations primarily as problems to be outmaneuvered, or as opportunities for the character of Christ to be formed more deeply in you?

Bring whatever you find honestly to the Lord and ask Him to transform it.

Then pray simply:

“Lord Jesus Christ, form in me true wisdom rather than mere shrewdness. Let the circumstances of my life shape me toward love and service rather than toward self-interest and manipulation. And let the disciplines of this Dormition Fast interrupt whatever patterns have formed in me without my noticing, and redirect them toward You.”

Being Orthodox on Purpose means submitting the calculating instincts our circumstances have formed in us to the discipline of genuine wisdom, so that the character of Christ grows where self-centeredness used to reign!

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