Archive for Hobbit

The Riddle of the Shrewd Steward

Posted in Homilies with tags , , , , on September 17, 2019 by timtrue

IDMS Chapel, 9/18/2019

Proper 20C


I’ve got a couple of classic riddles for you:

First, “What is the creature that walks on four legs in the morning, two legs at noon, and three in the evening?”

This riddle comes from Greek mythology, posed by the Sphinx. A man named Oedipus figured out the correct answer: man. . . .


This thing all things devours;

Birds, beasts, trees, flowers;

Gnaws iron, bites steel;

Grinds hard stones to meal;

Slays king, ruins town,

And beats mountain down.

This riddle comes from a story called The Hobbit. Bilbo and Gollum are having an epic battle of wits in the heart of the mountain; and Gollum posits this “tricksy” one. But Bilbo figures out the answer: time.


Jesus tells a similar riddle today about a man who is about to be fired from his job because his boss thinks he is dishonest, who then acts desperately and cleverly; and because of his actions his boss then commends him.

It’s a surprise ending! We’re left scratching our heads asking why. In fact, for two thousand years people have been asking why; and have come up with a lot of different answers, with very little agreement between them.

So, what we heard was that this guy was about to be fired, so he “sweet-talks” his way into favor with his boss’s customers; and this behavior impressed his boss.

Other versions of the Bible give us more detail. What this guy actually did was to go to one of the customers and ask, “Don’t you owe my boss a hundred jugs of olive oil?” And the customer answers, “Why, yes I do!” “Well then,” this guy says, “I have the authority to make it fifty. Would you like that? Now you only owe my boss fifty!”

This steward is shrewd!

Similarly, he goes to another customer who owes his boss a hundred containers of wheat and says, “Now you owe him only eighty.”

And the boss finds out! And he goes to his shrewd steward and says, surprisingly, “Well done because you have acted shrewdly!”

And for two thousand years, people who have heard this riddle have been saying, “But this guy just hurt you financially! How can you commend him?”

Just what is going on here, Jesus? Just what is the answer to your riddle?


So, here’s where I land on this. I’m not saying it’s the right answer—that I’ve figured it all out, et in saecula saeculorum, amen! Rather, it’s my best guess right now, at this point in my life, knowing what I know at this moment:

Letting go is to have and possessing is to lose.

That’s what I think Jesus is getting at in this story about this shrewd steward. To let go is to have; to possess is to lose.

Whahuh? Isn’t this just another riddle?

So, here’s what I mean. This guy—I just called him a shrewd steward—so, this shrewd steward is about to get fired and he knows it. What does he do?

Now, while he’s still working for his boss, while he still has the authority to make important decisions, he takes huge risks and gives up everything. He’s not going to have his cushy job anymore, he realizes; and he’s really got nothing to fall back on except for whatever pension he may or may not have saved up. And no one else is hiring right now—and, besides, he’s got only a bad reference anyway!

So, he throws caution to the wind and risks everything.

When he cut that customer’s debt in half—a hundred jugs of oil? Make it fifty!—and when he cut that other’s customer’s debt down, you know what I think he was doing? He was giving up his own commission!

It was his money he gave up, not his boss’s!

But why in the world would he do that? He was just about to be fired! He needed some extra cash in his pocket, to stockpile away as much as possible!

Instead, dishonest or not, he knew an important truth. This shrewd steward had learned that true freedom is not found in possessions. Rather, he learned that letting go is to have and possessing is to lose.

In my thinking, here is the answer to Jesus’ riddle. Here is how Jesus encourages all people to live. Freedom is not found in what we possess but in a generosity that stretches us to the extent of, even beyond, our means.

It’s not just Jesus who says this, by the way. Gandhi says it too:

Golden fetters are no less galling to a self-respecting man that iron ones; the sting lies in the fetters, not in the metal.

There is goodness as well as greatness in simplicity, not in wealth.


So, let’s think about what this means for us, here, at Imago Dei Middle School. What does it mean for us to be free of greed and wanting more? What does it mean for us to be generous?

Most of you met my daughter Emily. In seventh grade, she attended a private Episcopal school where many of the students came from homes with a lot of money. Quite a few of them lived in mansions. Some showed up to school in a Ferrari or a Maserati; others in Teslas.

So, one day Emily came home in tears. She had saved up her own money for about a year to buy herself an iPhone. I was so proud of her; she showed so much discipline. Anyway, she came home in tears on that day because she had dropped her iPhone on a concrete sidewalk and cracked the screen. “I’d ask for a new one,” she told me, tears streaming down her face, “but I know we don’t have the money. . . . But, Dad,” she continued, “the hardest part is that my friend Angela dropped her iPhone in the toilet and her mom just went out and bought her a new one the next day. It’s not fair!”

You ever feel like that: Other people have way more money than I do; it’s just not fair?

Yeah, me too.

But here’s what Emily did. Instead of thinking about things that weren’t possible, or that would take way too much time and focus for her to achieve, she looked around her immediate world and focused on the present. And she realized that already, here and now, she had much to be grateful for: friends, family, a warm bed at night, enough food; life’s simple yet profound pleasures.

What do you have that you are grateful for? You are part of a great school, a place where you are being challenged to grow into tomorrow’s leaders; surrounded by people who have your best interests at heart.

Also, think about the risks the shrewd steward took. Here at IDMS you are being encouraged to think and act in creative, innovative, risky ways.

You—all of you—have so much! Right here. Right now.

Throughout today and in the weeks ahead, remember this puzzling story from Jesus today, this riddle; and the challenge he leaves us all: letting go is to have and possessing is to lose.