By Manfred Kets de Vries
Managing ambiguity sounds noble in theory. In practice, it’s disturbing and exhausting. Take, for example, a recent “brainstorming session” I attended at a high-tech company. The major investor, who had just taken over, invited me to help figure out whether he’d bought a hidden gem — or a lemon.
I expected an intimate, strategic meeting. Instead, I walked into a full-scale corporate production. Every senior executive and mid-level manager had been summoned to the company auditorium.
The CEO, exuding the anxious energy of someone who suspects his days are numbered, stood on the podium. We were here, he said, to save the company through bold ideas.
What followed was not brainstorming but bureaucratic theatre. Executives stood up one by one to carve ornate, meaningless arguments from thin air. The underlying theme? “Give us more money, and we promise this time will be different. We will finally be successful.”
As the hours dragged on and my brain began quietly plotting its escape, something truly memorable happened.
The major investor — unknown to most in the room — rose from his seat, walked calmly to the stage, grabbed a marker, and drew a large zero on the flip chart. He looked around with the intensity of someone choosing the least unappetising item on a tragic menu.
Then he walked out.
The room erupted. Who was he? What did the zero mean? Protest? Art? A silent threat?
The CEO, pale, turned to me, reeling from the investor’s mysterious gesture, asked me what the zero meant.
I was sorely tempted to play guru, to try to decode it for him on the spot.
But I resisted the temptation to invent an immediate interpretation and instead offered a radical suggestion. I told him to sit with the discomfort. To listen to the buzz around the building. To let confusion do its work. And maybe to sleep on it.
To my surprise, he agreed.
Reflections on the zero
Left alone, I also stared at the zero.
Could it mean zero tolerance? That the investor’s patience had run out? Or zero hour? That time was up?
Or was it a declaration that all the talk, all the grand strategies and performance theatre, had added up to nothing — a hollow vacuum?
Knowing the investor, I suspected something more cunning. He wanted to inject not-knowing into a room drunk on certainty and buzzwords. He tried to disrupt the executives’ comfort zones. To shake loose a little real thinking.
Or maybe, like me, he just really hated meetings.
The next morning, the CEO told me that the incident had gnawed at him all night. He realised he’d been avoiding hard decisions. That inertia — and fear — had paralysed him. That he needed to act.
Inspired by the zero (and perhaps the absurdity of it all), he came up with a plan. A real one. One that addressed the company’s core problems.
And the silent investor was impressed. The CEO wasn’t fired. He was empowered. Somehow, not-knowing had saved the day.
The discomfort of not-knowing
Let’s be honest: not-knowing is hard. We’re wired to chase certainty. We want to fix problems — and to be seen fixing them. We rush to close loops, to tie off loose ends.
Even in coaching or therapy — where the job is to explore — we often find ourselves quietly preparing rescue missions. We want to offer answers, wisdom, closure.
But the truth is, telling people what to do rarely works. Insights that stick are the ones people arrive at themselves. Ownership matters.
And yet, if we can sit through the discomfort of not-knowing, space opens up — for reflection, creativity, even transformation. If we resist the urge to tidy the mess too quickly, we sometimes find that the mess itself holds the answer.
The English poet John Keats called this “negative capability” — the ability to remain “in uncertainties, mysteries, doubts, without any irritable reaching after fact and reason.” But it was easy for him to say so. He was a poet. He didn’t have to endure PowerPoint decks and Jeff from Accounting explaining “synergies.”
Learning to sit in the soup
Knowing things has its perks. It can make you rich. It earns trust, clients, speaking engagements.
But knowing when not to know — that’s a subtler, stranger art. It means resisting premature closure. Enduring the awkward silence. Sitting in the soup and not trying to dry yourself off too soon.
It’s not glamorous. It’s like forgetting your lines on stage and smiling anyway.
And yet — this uncomfortable space is often where the best answers come from. When I manage to sit in that uncertainty a little longer, problems sometimes shift or reveal hidden doors. The fog occasionally clears. Or I find a better place to wait out the storm — maybe roast a few metaphorical pearls while I think.
The strange gift of kōans
That particular moment in the boardroom was a corporate version of a kōan — those riddles Zen masters lob at students to break the grip of logic and open the mind to something deeper.
Kōans are meant to disturb. To puzzle. To make your usual thought patterns sputter and fail.
Zen, which comes from the Sanskrit dhyana (meditation) and sunya (emptiness), is the practice of “thinking about not thinking.” And Zen masters use kōans as a way of bypassing the analytical mind. They’re not gibberish, but carefully constructed provocations meant to stir something beyond rationality. In this sense, Zen was centuries ahead of modern coaching, therapy, or consulting: all practices that, at their best, invite people to wrestle with their own minds.
Wrestling the mind
The German American psychoanalyst Erich Fromm once likened enlightenment to moving from a cave full of shadows into the light of reality. But the transition isn’t always peaceful. It’s often confusing, slow, and weirdly funny.
In therapy, we call this “working through” — recognising old patterns, hitting them headfirst, struggling with them, and slowly shifting. Kōans work the same way. The goal isn’t to “solve” the riddle — it’s to let it transform you.
Which is why kōans must be strange. If they made sense too quickly, they wouldn’t work. They’d be answers, not instruments of insight.
Take the classic kōan: Two monks argue. One says, “The flag is moving.” The other: “No, the wind is moving.” A third walks by and says, “Not the flag. Not the wind. The mind is moving.”
You’re either on the brink of illumination — or wondering if you need a drink.
But that’s the point. You’re meant to wrestle with the kōan. To be disturbed. To let it get under your skin until something new starts to stir.
Therapy, coaching, and absurd insights
Helping others isn’t about handing over an answer key. It’s about inviting them into their own confusion — and being willing to sit with them while they squirm.
Sometimes, when a client is stuck, I borrow from the kōan playbook. I prescribe the problem as the cure.
Tell the anxious to worry harder. The control freak? Plan even more obsessively.
The procrastinator? Schedule their procrastination.
It’s therapeutic judo — using their own energy to trip them into insight.
It’s like the paradoxical command: “Be spontaneous — right now.”
Spontaneity immediately disappears. You’re left awkward and twitchy. Welcome to your own Zen trap.
Kōans, like life, are riddles with no neat punchlines. They force you to question everything — including your desire for tidy answers.
This is why coaching, therapy, and spiritual practice often feel similar. All require enduring ambiguity. All ask us to let go of the fantasy of final certainty. All involve the strange, maddening process of unlearning as much as learning. And in the end, you don’t get a trophy. You get a better question.
Final thoughts: tripping toward insights
Let’s be honest. Not-knowing sucks. It’s itchy, slow, often humiliating. But if you manage to stay in it — just a little longer — real rewards may emerge.
Negative capability is more than a poetic phrase. It’s essential survival gear for a world that doesn’t make sense. It helps you face problems that don’t resolve neatly, choices without clear outcomes, and lives that don’t unfold according to plan.
Working with a kōan-like situation is like training your mind to deal with this negative capability. It is like letting a kōan work on you. Granted, it rearranges your mental furniture without permission. It’s not comfortable. But it can be profoundly healing — like a deep tissue massage for your worldview.
And once in a while, the process yields more than insight. It yields transformation.
So the next time someone asks you whether you prefer purple or eight — smile knowingly.
You’re already halfway to enlightenment.