A story about how the best intentions can quietly wander off course — and how to find the way back
"Non progredi est regredi." — To not move forward is to move backward.
Though sometimes we're so busy moving, we don't notice which direction we're headed.
There's an old story about a merchant in medieval Tuscany who owned an orchard outside Florence.
The orchard had won awards once. People traveled from neighboring villages just to taste the fruit. But somewhere along the way — nobody could say exactly when — it had become merely adequate. The trees still produced. The fruit was still... fine. It just didn't make anyone's eyes light up anymore.
You've probably seen a place like this. Maybe worked in one. The strange thing about these places is that everyone inside is genuinely trying. There's no villain twirling a mustache in the corner. Just good people, doing reasonable things, wondering why the magic seems to have wandered off.
The merchant had a head gardener named Berto.
Berto was the kind of person you'd want at your dinner table — warm, agreeable, always ready with an encouraging word. When the merchant had an idea, Berto's instinct was to support it. Partly because he respected the merchant, partly because he'd learned that bosses generally prefer "yes" to "let me tell you seventeen reasons that won't work."
We've all been there. Sitting in meetings thinking "I'm not sure about this" while our mouths say "Sounds good!" It's not cowardice. It's the sensible calculation that being wrong and quiet is survivable, while being wrong and loud is memorable for all the wrong reasons.
When the merchant suggested planting in the northern field — the one that turned into a small lake every spring — Berto had reservations. But the merchant seemed confident, and confidence is contagious, and besides, what if the merchant knew something about drainage that Berto didn't?
The field flooded. The crop was lost. A family of ducks moved in and seemed quite pleased with the arrangement. They held a small celebration. One of them was later seen wearing what appeared to be a tiny crown made of wheat stalks. The ducks, at least, had found exactly what they were looking for.
"Errare humanum est." — To err is human.
And honestly, the ducks were thriving.
When Success Creates New Puzzles 📈
The merchant's business grew. He bought a second orchard and needed someone to manage both properties. He chose Berto, which made sense — Berto was steady, showed up every day, and had never once made the merchant feel foolish.
Now Berto needed to choose his own replacement. He had three candidates:
Marco was brilliant with irrigation. His section of the orchard outperformed everyone else's by a wide margin. He also asked a lot of questions — not to cause trouble, but because that's how his mind worked. "Why do we do it this way?" "Has anyone tried this instead?" Good questions. Also tiring, if you were on the receiving end after a long day and just wanted to go home and not think about optimal root spacing.
Elena had developed composting techniques that other workers were starting to copy. Her trees were magnificent. She was also ambitious — always volunteering for more responsibility, always pushing to try new approaches. Some people found this energizing. Others found it... a lot.
Paolo was eager and agreeable. He took excellent notes. He'd learned by watching: support your leadership, don't make waves, and good things follow. He had a gift for making everyone feel comfortable.
Berto chose Paolo.
It wasn't a bad choice. Paolo had real qualities — reliability, positivity, a genuine desire to help. The question wasn't whether Paolo was good. The question was whether "good" was the same as "what the orchard needed."
"Similis simili gaudet." — Like is drawn to like.
This isn't a character flaw. It's just something worth noticing about how choices get made.
The Art of Looking Busy 🔄
Paolo stepped into his new role determined to do well.
He held meetings when problems surfaced — because that's what responsible people do. He documented concerns carefully — because accountability matters. He used phrases like "Let's circle back on this" and "I'll look into it" — because these are the phrases of someone taking things seriously.
Here's the thing about "I'll look into it." It's almost never a lie. The person saying it genuinely intends to look into it. But then Monday becomes Tuesday, and Tuesday becomes "where did March go," and somehow the looking-into never quite happens. The intention was real. The follow-through got lost somewhere between the third meeting and the fifth urgent request.
Paolo kept a small leather notebook where he recorded concerns. He was quite proud of it. The leather had worn soft at the edges from being pulled out so often. Inside: careful handwriting, organized by date, cross-referenced by topic. A monument to thoroughness.
What he'd never thought to add was a column for "resolved." That would have been a much shorter list. But the notebook itself felt like progress. It was tangible. You could hold it. You could show it to people. "See? I'm tracking everything." The notebook was evidence of effort, even when effort and results weren't the same thing.
The workers who knew the trees best gradually stopped bringing concerns to Paolo. Not out of frustration, exactly. More like the quiet acceptance of someone who's tried the same door a dozen times and has concluded, reasonably, that it's not going to open.
Marco eventually left for a vineyard across the valley. They'd offered him something the orchard couldn't: the chance to actually try his ideas. He didn't leave angry. He left a little wistful. He'd liked the orchard. He just couldn't see a future for himself there.
Elena followed a few months later. A merchant in Siena had tasted fruit from her section and tracked her down. He offered her something she'd never had: the authority to actually implement her techniques. She was packed within the week.
"Aquila non captat muscas." — The eagle doesn't catch flies.
Talented people need room to stretch. When they can't find it, they go looking elsewhere. This isn't disloyalty. It's nature.
The Expert's Dilemma 🔍
Eventually, even the merchant noticed something was off. Customer complaints had increased. The fruit wasn't what it used to be.
"We need an outside perspective," he announced. "Fresh eyes." This was genuinely wise — every organization develops blind spots, and outside expertise can illuminate what insiders have stopped seeing.
They found two candidates.
Lucia had spent fifteen years diagnosing problems in orchards across Tuscany. She was, by all accounts, excellent at her job. Within an hour of walking the property, she'd identified six significant issues: drainage patterns that needed attention, pest pressure that had gone unaddressed, pruning practices that had drifted over the years.
She was right about all of it. She presented her findings clearly and directly — facts, evidence, recommendations. No nonsense.
Here's what Lucia hadn't learned yet: being right is only half the job. The other half is helping people hear you. Every true thing she said, though accurate, landed in a room full of people who suddenly felt exposed. The merchant heard "you've been blind." Berto heard "you've been failing." Paolo heard "your notebook was pointless." None of that was what Lucia meant. But meaning and impact don't always match.
Enzo took a different approach. He walked the property for about ten minutes, spent a pleasant interlude befriending a cat (the cat seemed skeptical but eventually came around), and then presented his assessment: the orchard had real potential. The fundamentals were sound. With some attention to presentation — nicer baskets, perhaps some colorful ribbons to distinguish varieties — customers would respond beautifully.
Was Enzo wrong? Not entirely. Presentation genuinely matters. But Enzo also saw only what he was equipped to see. He couldn't diagnose root systems or pest cycles. So he focused on ribbons, because ribbons were something he understood.
The merchant chose Enzo.
This is worth sitting with, because the merchant wasn't foolish. He was human. Given a choice between "everything you've built has serious problems" and "everything you've built just needs some polish," most of us lean toward polish. It's not denial. It's the very understandable desire to believe our work has value.
Lucia moved on to other orchards. She was right about everything, and it hadn't mattered. Somewhere along the way, she might have wondered if she needed to learn something about how to deliver hard truths in ways people could actually receive.
"Suaviter in modo, fortiter in re." — Gentle in manner, firm in substance.
The best messengers eventually learn to be both.
The Long Quiet 🍂
Years passed. The orchard continued.
From the inside, it never felt like decline. More like a very slow settling. The fruit grew a little smaller each year, but gradually enough that each year's harvest seemed normal compared to the one before. This is how standards drift — not through sudden drops, but through the quiet recalibration of what "normal" means.
Enzo did his job conscientiously. He created a rating system for tree health — one to five apples — and gave nearly everything a respectable four. The ribbons were implemented beautifully. Red for one variety, yellow for another, blue for the ones that had become difficult to identify. The baskets looked wonderful. What was inside them... well, at least the presentation was nice.
Berto eventually retired. They held a ceremony where people said genuinely kind things about his loyalty and dedication. And those things were true — Berto had been loyal. He had been dedicated. He had showed up every day for decades. The ceremony honored real virtues. It just couldn't honor what might have been.
One autumn, an old worker named Tommaso walked through groves he'd tended for thirty years. He remembered when this place had felt special. He thought about saying something — about trying one more time to explain what he was seeing.
Then he thought about all the other times. The polite nods. The notes taken. The genuine intentions that somehow never translated into change.
Tommaso kept walking. Not because he'd stopped caring. Because caring, without the ability to act, eventually becomes its own kind of weight.
The merchant's grandchildren eventually inherited the property. They found an old award in a storage room — first place, regional competition, decades ago. The fruit in the illustration looked nothing like what they were growing now.
"Must have been a different orchard," one of them said.
"Tempora mutantur, nos et mutamur in illis." — Times change, and we change with them.
Though not always in the direction we'd choose.
What Gardens Teach Us 💭
Here's what this story isn't: an accusation. Berto wasn't malicious. Paolo wasn't lazy. The merchant wasn't foolish. They were people navigating uncertainty the best way they knew how.
That's what makes these patterns so tricky. There's no villain to remove. Just a series of small moments — each one understandable, each one human — that somehow added up to something nobody intended.
So what actually helps? A few thoughts:
Create channels for difficult questions
Marco's questions weren't comfortable, but they were valuable. The orchard lost something important when those questions stopped being asked.
Try this: In your next team meeting, explicitly invite one concern or question that might be uncomfortable to raise. Make it normal, not exceptional. "What's one thing we might be avoiding talking about?" Then — and this is the hard part — respond with curiosity instead of defense.
Distinguish motion from movement
Paolo's notebook was full of activity. But activity and progress aren't the same thing. The orchard didn't need more documentation. It needed fewer unresolved problems.
Try this: Once a quarter, look at your team's work and ask: "What's actually different now than it was three months ago?" Not "what did we do" but "what changed." The distinction matters more than it seems.
Learn to deliver hard truths gently
Lucia was right about everything. It didn't help, because nobody could hear her. The message matters, but so does how it lands.
Try this: Before delivering difficult feedback, start by genuinely acknowledging what's working. Not as a trick — because something almost always is working — but because it helps people stay open to what comes next.
Give your best people room to grow
Marco and Elena didn't leave because they were unhappy. They left because they could see the ceiling. Talented people need challenges that match their abilities.
Try this: Ask your strongest contributors what they wish they could work on. The answer might surprise you. And acting on it might mean the difference between keeping them and watching them leave.
"Docendo discimus." — By teaching, we learn.
And sometimes the most important teaching is simply making space for others to speak.
An Invitation, Not an Indictment
If pieces of this story feel familiar, that recognition is worth something. Not as evidence of failure — but as the beginning of a conversation.
Most of us have been Berto at some point — wanting to support, uncertain whether to push back. Most of us have been Paolo — learning the unwritten rules and following them faithfully. Most of us have been Tommaso — sensing something was off but unsure whether speaking up would help.
These aren't character flaws. They're human responses to complicated situations.
The interesting question isn't "who's to blame?" The interesting question is: "What would make it easier to speak honestly here?" Sometimes that's structural — regular retrospectives, explicit invitations for feedback. Sometimes it's cultural — leaders visibly thanking people who raise uncomfortable topics. Sometimes it's just one honest conversation between two people who trust each other.
The orchard can still produce magnificent fruit. It just needs someone willing to look clearly at what's happening, and someone else willing to listen.
"Dum spiro, spero." — While I breathe, I hope.
And hope, combined with honesty, is how things actually change.
The strangest thing about struggling teams is how everyone inside them is usually trying their best. There's no sabotage. No villainy. Just people doing sensible things that somehow add up to puzzling outcomes.
The good news is that the same principle works in reverse. Small shifts, consistently applied, can add up to remarkable change. It doesn't require heroes. It just requires people willing to ask "What would make this better?" — and other people willing to actually hear the answer.
That's really all it takes. Curiosity. Honesty. And the willingness to believe that next season could be better than this one.
After all, even the ducks figured out how to make something good from an unexpected situation. We can probably manage the same.
"Faber est suae quisque fortunae." — Each person is the architect of their own fortune.
And sometimes, the architect of their team's fortune too.