What If You Followed the Mistake?
On fear, failure, and the unexpected paths that lead to better work.
It was an uncomfortable silence — even though it took place in the digital sphere, I could almost imagine the other side.
One of my executive MBA students had just finished recounting the moment they completely froze. It happened early in their time at one of the big tech firms. Minutes in, they realized they were in the wrong meeting… and the only way out was through.
They cut the call. Admitted the misunderstanding. Rescheduled.
And they told this story, years later, to a group of peers as part of a session I run on failure.
“It’s still one of the most embarrassing moments of my career,” they said. “But it changed the way I prepare for everything. It sharpened something in me.”
For some, a moment like that passes. It becomes a story, a lesson, a sharpening—as it did for this student.
But for others, it lingers.
It sinks into the muscle memory of decision-making. Every button press, every presentation, every step into the unknown becomes loaded.
Not with possibility—but with dread.
There’s a word for that feeling.
For the fear that keeps the brush from touching the canvas, the finger from pressing “send,” the idea from ever leaving the safety of your head: kakorrhaphiophobia.
It’s a long, ancient-sounding word, and its roots are revealing: kakos, meaning bad or evil; rhaphe, to stitch; and phobia, fear. A fear of stitching something wrong into the fabric. A fear of being flawed—and of that flaw being seen.
It sounds like something out of a Greek tragedy. But it’s surprisingly common in boardrooms, brainstorming sessions, and design studios. It shows up in perfectionism, in risk aversion, in the endless editing before a project ever launches. It’s the internal script that whispers: “Don’t make a move unless it’s the right one. Don’t speak until it’s brilliant.”
I believe in preparation. But at some point, it stops being a launchpad—and becomes a loop.
The fear of getting it wrong leads people to cling to what’s already been validated. They over-prepare, over-edit, and ultimately under-create.
In trying to avoid failure, they avoid movement.
Failure for all!
Well, not really.
Let’s be clear: not every industry needs failure. In aerospace engineering or heart surgery, error isn’t a step—it’s a catastrophe. In those domains, perfection isn’t just a virtue—it’s a requirement.
But in creative work—in art, writing, entrepreneurship, and in the very thing the corporate world claims to want most—innovation—failure plays a different role. It’s not the opposite of progress; it is progress. It marks the place where newness begins.
Without mistakes, there’s no friction. Without friction, there’s no movement. And without movement, there’s no transformation—only repetition.
So while the pilot must never improvise, the painter must. The innovator must. The entrepreneur must. Otherwise, we’re not making anything new—we’re just making things again.
But are we preparing our teams for that kind of failure? I don’t think so.
What surprises me isn’t that failure is hard to talk about. It’s that in most organizations, we never really do.
We expect our executives to be resilient, innovative, willing to take risks. But we rarely give them the space—or the language—to explore what failure actually feels like, or how it functions in creative work.
So every year, I dedicate one session to discuss failure and mistakes, and I ask my students—mid-career leaders, most of them managing people and strategy in large organizations—to reflect on their relationship with failure. And every year, I’m struck by the honesty that pours out once the door is open.
Failure is my biggest fear. But also the source of my biggest growth.”
“I was taught from childhood that failure is not an option.”
“I keep a journal of every mistake—my own Book of Life.”
The reason I dedicate a full session to failure isn’t because I believe we should celebrate it. I’ve never really subscribed to that culture. The whole “let’s celebrate failure!” mantra often feels shallow—even counterproductive. Failure isn’t fun.
But I’ve never worked a traditional job. I grew up inside entrepreneurship. Failure wasn’t abstract—it was a regular visitor. Sometimes it meant rethinking everything on a Tuesday. Or crawling into bed, frustrated by a mistake I made.
It taught me that creativity can’t exist without mistakes. That failure isn’t something to recover from—it’s something to work with.
The Paradox of Avoiding Failure
“The moment you think you are successful, failure will be there for you.”
Artist Maurizio Cattelan
That line hits home—because it speaks to one of the strangest truths I’ve seen again and again in my own work and in the founders and executives I work with: Success, for all its rewards, has a way of narrowing us.
I’ve come to think of it as the paradox of avoiding failure. The more we try to protect ourselves from it, the more we back away from the very things that created momentum in the first place.
In the early days, everything’s fluid. You try, you adjust, you move. There’s nothing to lose—so there’s freedom in the risk. Founders zigzag by necessity. Artists make with what’s at hand. The constraint is part of the creativity. And then—something works. A product takes off. Capital comes in. People start paying attention. And quietly, something shifts.
I often sketch this pattern for leadership teams—how the mindset that launched success slowly morphs into one that just wants to preserve it. The improvisation fades. The focus turns to not messing it up.
It’s not just a founder’s problem. Artists feel it too. In a documentary, Thom Yorke of Radiohead described it like this:
“Well, this is what they want me to do, this is what they want to hear. So I’ll do more of this, cuz this is great... and they love me. Suddenly people start giving you money as well. So then you’ve got money and you get used to this lifestyle. And you don’t wanna take any risks…”
We can’t escape that pull. But the difference is that artists are often more aware of it. They’ve learned to notice when the work starts drifting toward comfort. When safety starts dressing itself up as style.
“The very act of trying to prevent failure,” I remind them, “can make it more probable.”
And that’s the real danger. Not just failure itself—but the slow shrinking of possibility. The openness we had as beginners gets replaced by the fear of breaking what we’ve built.
As one student put it, summing up the flaw in many executive cultures:
“We’re told to take risks. But no one gives us permission to fail.”
That sentiment isn’t anecdotal—it’s backed by data.
In a 2019 study of 1,000 professionals by Drs. Nick van Dam, Jacqueline Brassey, and Arjen van Witteloostuijn, over 40% reported experiencing fear of failure 20 to 40 percent of the time or more—a clear sign of how deeply this fear is embedded in day-to-day work.
We glorify risk after it pays off—but rarely create real space for it before we know the outcome.
Maybe it’s not about tolerating failure—that sounds like something we simply endure. Maybe it’s about recognizing it as part of how creative work moves. Because creativity doesn’t live in the safe center. It shows up at the edges—in the questions we can’t yet answer, the awkward middle, the things that don’t quite work.
To keep making things that matter—even after success—we have to return, on purpose, to the mindset that started it all. To stay open. Curious. Willing to be wrong. Willing to begin again.
In Zen, they call it shoshin: beginner’s mind. In business, it might be the rarest form of courage.
What You Do With a Mistake
So what do we do with all of this?
We’ve been talking about failure, but let me pause to make a small distinction—because not everything that goes wrong is a failure. A mistake is usually a misstep. A line that didn’t land. A test that missed. It’s local, often fixable. Failure feels larger. It’s when the whole project, pitch, or vision collapses.
But in creative work, they’re often tangled. Sometimes a mistake leads to failure—because we resist it. And sometimes, what we call failure is really just a mistake we gave up on too early.
One of the most powerful insights I’ve come across came from Dr. Ellen Langer of Harvard University—a renowned psychologist known for her work on mindfulness, and a late-blooming painter herself.
I interviewed her for my podcast Business Artistry (yes, that’s the name. No, I didn’t win points for originality), where we spoke about how creative people respond when things go off track.
She described four typical reactions to mistakes—and what separates the reactive from the truly innovative:
Discard the work entirely.
Ignore the mistake and push through.
Try to erase the mistake and restore the original vision.
Reinterpret the mistake—and let it change the work.
That fourth response—the reinterpretation—is where real innovation lives. It’s not a coping mechanism. It’s a kind of collaboration with the unexpected.
“Mistakes are often defined by rigid expectations,” she told me. “But when we’re mindful, they become discoveries.”
You see this across creative disciplines. In abstract painting, the drip becomes the piece. In jazz, a wrong note opens a new phrase. In startups, the failed product becomes the feature that sparks something new.
Let the Work Go Wrong
Kakorrhaphiophobia keeps us from making mistakes. But worse—it keeps us from following them.
We think we’re staying safe by avoiding error. But in creative work, safety is often the most dangerous choice. It leads to polished mediocrity. To familiar outcomes. To work that may be admired, but never remembered.
The most compelling art, the most surprising innovation, the most alive work—these things are rarely the result of flawless execution. They’re the result of movement. Of tension. Of the artist, or founder, or thinker saying:
What just happened? What if I didn’t fix it? What if I followed it instead?
Maybe that’s what this is really about. Not failure, per se. But wrongness—the kind that bends an idea off-course, away from what you expected, toward something truer.
Let the sketch go sideways. Let the prototype fall short. Let the sentence unravel. And then… listen to it. Work with it. Walk with it.
Because sometimes, the mistake isn’t the end.
It’s the beginning of something the original idea couldn’t reach on its own.
Up next week: how companies and creative leaders relate to mistakes—how they frame them, respond to them, and what that tells us about the cultures they’re building.
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Thanks
Nir