Tag: humility

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Business Startups Venture Capital

Great Open-Field Runners

The plane was somewhere over Nebraska. Dick Kramlich sat across from me. We were on the same board then, and the rides together had become their own kind of conversation. He talked 1:1 the way certain men do when the clock has stopped mattering: without hurry, without the need to impress.

I asked him the question that had been riding with me for a while. After decades of sitting with founders, after watching tens of companies rise or disappear, what was the difference? What separated the ones that made it from the ones that simply ran out of road?

He didn’t answer right away. He looked out the window for a moment, then back.

They had done a study once, he said — a hard look at outcomes, not opinions. What it found stuck with him ever after: the companies that survived were almost never the ones that had stuck to the plan. Success required the pivot. Not once, but again and again, until the company that arrived was almost unrecognizable from the one that had set out.

Then he gave the image that has stayed with me longer than any spreadsheet or term sheet.

He looked for great open-field runners.

Not the ones who could only run between the tackles, powering straight ahead into the line. The ones who could see daylight where it did not yet exist, who could plant a foot and cut, who understood that the shortest path is rarely the one that gets you home. Zig and zag. Feel the defense shift and refuse to be trapped by the original play call. Keep the ball moving toward the only thing that matters: the space that opens when you stop insisting the field must look the way you imagined it on the whiteboard.

I have carried that sentence for years. Great open-field runners.

It never felt elegant inside the room.

Kramlich had seen enough to know that the founders who could do this were rare. The ones who lasted treated the plan the way a great running back treats the designed play: as a starting point, not a contract with the universe. They trusted the daylight more than the diagram.

I think about him sometimes when the ground shifts under something I thought was settled — when a strategy that once felt inevitable begins to feel like a trap, when the clean line on the page starts to look like a cage.

Dick is gone now. The rides are over. But the image remains, clean and sharp as the day he offered it at thirty thousand feet: a runner in open space, eyes up, cutting toward the light that only appears after you abandon the path you thought you were supposed to take.

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Living

The Compound Interest of Ignorance

There’s an emotional navigation system within all of us, an internal map of behavior and consequence. We navigate by way of kindness, curiosity, and empathy.

Most days, we manage to keep the car on the road. But there is a particular intersection on this map, one that rarely ends well for anyone who finds themselves there, either driving or just walking by.

It’s the intersection where Annabel Monaghan located a particularly difficult archetype in Nora Goes Off Script. She describes it, with a precision that feels like the pop of a bubble, as “the corner of arrogance and cluelessness.”

“At the corner of arrogance and cluelessness, you find the worst kind of person.” (Annabel Monaghan, Nora Goes Off Script)

Indeed.

It’s easy, and frankly quite satisfying, to point fingers. We can all summon the mental image of someone parked right at that corner.

Perhaps it was a micromanaging boss who had never performed the basic function of the department. Perhaps it was a self-styled intellectual whose confidence was inversely proportional to their subject-matter expertise. We’ve all felt that specific, teeth-gritting frustration when faced with the wall of certainty erected by the fundamentally uninformed.

Arrogance on its own is, of course, rarely endearing. But there’s a difference between earned arrogance—the abrasive confidence of someone who actually knows what they are doing—and this unholy alliance. Pure arrogance is often about results; it says, “I am the best, and here is my proof.” It’s difficult to live with, but it is at least based on a form of reality.

Cluelessness, too, has its own nuances. We are all clueless about something (a truth that keeps life interesting). There is an innocence to genuine ignorance, an implicit opening for growth. To be clueless and know it is a temporary state. It’s the raw material for humility and learning.

But Monaghan’s observation zeros in on the specific danger when these two states merge.

Arrogance and cluelessness don’t just coexist; they compound.

This isn’t just a simple mistake (cluelessness) or just a big ego (arrogance). This is a system where the arrogance actively prevents the realization of the cluelessness.

The arrogance acts as a sturdy shield, deflecting any data, any feedback, any reality-check that might reveal the cluelessness underneath. The clues are everywhere, screaming from the spreadsheets or the strained smiles of everyone around them, but the arrogance filters them all out. This person cannot learn because the primary tool for learning—admitting you don’t know—is precisely what the arrogance forbids.

When you find yourself arguing with a person at this intersection, you aren’t arguing about facts. You aren’t arguing about solutions. You are trying to breach a fortress that has decided that the external world must adapt to its inner perception.

The “worst” part of it, the thing that makes it so toxic, is the casual destruction it wreaks. The person at this corner is navigating with a map they have drawn themselves, one that ignores all existing roads, all traffic lights, and every standard convention of behavior. They crash through the lives and efforts of others, convinced all the while of their own perfect navigation.

The hardest truth to swallow, though, isn’t about them. It’s about us. Because if we find this so true of others, the final realization is that none of us are immune to the lure of that corner. It’s an easy intersection to drift into. Whenever our confidence outpaces our real-world competence, whenever we get a tiny bit of power and a tiny bit of success and we think we know, we are in danger.

We are all just a bad day, a stressful project, or a momentary inflation of ego away from parking right at that corner ourselves. The antidote to that specific, devastating brand of arrogance isn’t trying to become more right; it’s remembering how deeply, often, and completely we are wrong.

Stay humble, stay foolish.

Categories
Business Living

From Know-It-All to Learn-It-All

Momentum is a strange phenomenon. In physics, it is simply mass times velocity. But in human organizations, it is tradition multiplied by ego. When a ship reaches a certain size, its sheer mass resists any change in direction. Microsoft, a little over a decade ago, was the ultimate corporate supertanker. It was massively successful, incredibly profitable, and dangerously stagnant.

When Satya Nadella took the helm, he inherited a culture defined by its own historic brilliance. They were the smartest people in the room, and they knew it. But in a world moving faster than anyone could comprehend, being the smartest person in the room quickly becomes a liability. It creates a defensive posture. You spend your energy protecting your status and proving your intelligence rather than exploring the horizon.

As the observation goes, Nadella had to turn this bigger ship. His mechanism for doing so wasn’t a massive restructuring or a ruthless wave of firings; it was beautifully, disarmingly simple. He told his organization that they were going to make a fundamental, psychological shift.

“We’re gonna go from being a know-it-all to a learn-it-all culture.”

This isn’t just a corporate soundbite; it’s a profound philosophical pivot. The “know-it-all” operates from a place of fragility and fear. If your identity is built on knowing everything, any new information that contradicts your worldview is a threat that must be neutralized. A “learn-it-all,” however, operates from a place of abundance and curiosity. Contradictions aren’t threats; they are invitations to expand.

Looking inward, it is striking how easily we slip into a “know-it-all” posture in our own lives. Competence is deeply comfortable. When we get good at our jobs, our daily routines, or navigating our relationships, we build a fortress of certainty around ourselves. We stop asking questions because we assume we’ve already mapped the territory. We begin to ossify.

To adopt a learn-it-all mindset requires something deeply uncomfortable: vulnerability. It means walking into a room and quietly accepting that you might be wrong. It means replacing the urge to provide a quick, authoritative answer with the patience to ask a better question. It means letting go of the ego’s demand to be the expert.

The turnaround of Microsoft wasn’t just about a pivot to cloud computing or new product pipelines. It was a quiet victory of humility over arrogance. It was the realization that in an ever-changing world, the ultimate advantage isn’t what you already know, but how fast—and how willingly—you are prepared to learn.

We are all steering our own ships through shifting waters. The moment we decide we have nothing left to learn is the exact moment we begin to sink.