ISSUE #027 | THE LEADERSHIP CONTRARIAN
The first night, we had dinner at the Inn. It was spectacular. And because we were staying right there, we didn't have to drive anywhere, we just took a walk. Dusk was thinning. The stars were starting to come out. And then, in the air just over the dirt road, we saw lights.
They weren't stars in the distance. They weren't a truck coming down the road. They weren't some porch light way off through the trees. These were lights hovering in front of us, blinking on and off.
One blinked on, hung for a moment, then went dark. Another, ten feet to our left. Then a pair somewhere out in the field. There weren't many, maybe twenty in the whole stretch of road, and Kathryn and I just stood there in the middle of the dirt road, barely holding onto what was left of dusk, watching these little lights blink on and off in the air around us.
At first, we didn't know what we were looking at. And then it hit us, almost like the realization caught us off guard. Fireflies. We'd never seen fireflies before. Lightning bugs, depending on where you grew up. And once you've seen them, you understand why entire generations of kids have been sent out into the yard with mason jars and instructions to "just go play." My friend Ryan put it perfectly later: you feel like you're hallucinating.
We were mesmerized, and we went back out three more nights just to see them. In California, where we're from, those don't exist.
Standing there on the dirt road, I noticed how hard it was to actually watch them, to keep my eye on one. I couldn't see them when they weren't glowing. And I couldn't predict where they'd appear next. You can't see the bug at all when it isn't glowing, it's dark, the bug is small, and it's darting through the air the way flying insects do. Daylight would let you track the flight path. Night doesn't.
So all you have is the blink. And the blinks don't follow a rhythm. They're not on a metronome, those flashes are mating signals, and I was told each bug has its own pattern, but to an untrained eye in the middle of a Vermont field, they look completely random. One blinks twice over there. Five seconds of nothing. Then one blinks once over here. Then three in a row off to the right.
There's no sound. And you can't echolocate. Yes, I said echolocate. And you can't anticipate where to point your eyes. By the time your gaze arrives, the light is gone, and the bug is somewhere else.
It's wondrous. And it's almost impossible to track.
I stood there long enough on the third night to realize I was looking at a near-perfect picture of something I've been trying to put words to for a while.
Volatility.
A Series On VUCA
Before I explain what I'm on about, let me give you a quick note. This is the first issue in a four-part series on VUCA — Volatility, Uncertainty, Complexity, and Ambiguity.
The framework came out of the U.S. military, and over the last two decades it's been adopted across business, politics, and international affairs because it names something the old playbooks couldn't: why disruptions that used to hit once a decade now seem to be part of our everyday lives. I wrote our first full piece on VUCA back in Issue #002.
This series unpacks it one letter at a time. We start with Volatility.
What Is Volatility
Volatility is what I'd call a fuzzy word. It can mean multiple things to multiple people. Everyone thinks they know what it means, but they're not really sure. It's one of those words that gets used loosely.
Volatility is how much, how fast, and how often something changes.
The fireflies were the moment it clicked for me. But I'll be honest, being in awe of something isn't always the same as understanding it. So let me give you a more direct illustration.
Take ocean tides. Low volatility tides change slowly, water rises and falls within a narrow range, on a predictable schedule. Two feet up over several hours. Two feet down. Boats, docks, coastal businesses can plan around it easily.
High volatility tides change dramatically. A king tide can leave boats sitting in mudflats at low tide and flood roads and docks at high tide. The system is still moving, it's just moving much harder.
Here's the part that matters most: volatility and predictability are not the same thing.
Tides can be highly volatile and still predictable, because the lunar and seasonal patterns are known. But when a storm hits unannounced, or an earthquake out at sea triggers a tsunami, the tide becomes both volatile and unpredictable. A sudden event resets what you thought you knew.
Volatility comes from unexpected events or unexpected human behavior.
The same is true in business. If you run a retail company, December is volatile every year. Demand swings hard. But you've seen it before and you can plan for it.
The real problem is when volatility is both high and unpredictable.
Nobody in January 2026 was doing quarterly planning and anticipating a war with Iran that would send fuel prices through the ceiling and hold them there through the summer. Nobody put "Amazon fuel surcharge" in their forecast, yet there it was, tacked onto most of their orders. You may have expected costs to drift up across the year. You didn't expect them to spike that hard in sixty days.
That's the difference between a manageable swing and a shock. Between predictable and unpredictable, that's where leaders get in trouble. When the complexity around you outpaces the capacity inside you, you freeze, you make mistakes, your stress climbs.
Predictability increases confidence. When you can't predict, when tomorrow stops looking like something you can plan for, confidence erodes. Decisions get harder and the margin for error shrinks fast.
Are You Experiencing This?
I want to ask you directly, because most leaders feel this but haven't named it.
Are you seeing more volatility in your business right now? More unpredictability in your sales pipeline, customers behaving differently than they were six months ago? More difficulty forecasting, hiring, vendor reliability, financing, or cash flow? Has your marketing produced different results than the same effort would have a year ago? Did you absorb a shock this year that you genuinely didn't see coming — a price spike, a key person leaving, a regulatory shift, a customer pulling back without warning?
Are you feeling the increased pressure?
If any of those land, you're not just struggling with execution. You're navigating an environment that has genuinely changed.
Here's the part I need you to see clearly. This isn't a temporary disruption we're pushing through on the way back to some calmer normal. For most of the last decade, the baseline level of volatility in business has been rising. It used to be that a real disruption hit once every ten years or so, a recession, a market shift, a geopolitical event with economic ripple effects. Now it's quarterly. Sometimes monthly. Sometimes weekly.
What changed isn't just the frequency. The nature of the challenge changed.
Why the Old Response Doesn't Work
Here's the trap most leaders fall into.
When volatility increases, the instinct is to work harder, plan more carefully, or find a better strategy. There's nothing wrong with any of that. But if the operating environment has shifted at a fundamental level, incremental adjustments to what you're already doing won't be enough. You don't just need better tools. You need to grow as a leader. And the leaders working alongside you have to be growing with you at the same time, so you can trust their capacity to handle what's coming.
There's another side to it. Trusting their capacity is one part. Equipping them for what's coming is the other, and that's on you as the senior leader. You don't just run a company. You steward one. And that includes the people inside it.
Here's the logic underneath it. The way Kathryn and I think about leadership development, and the way we coach the leaders we work with, comes back to four premises.
1. Structure determines performance. The structure of your thinking, your beliefs, your decision-making instincts under pressure. That structure produces the leadership that comes out of you. Different structure, different leadership.
2. You are a structure. You have an inner game and an outer game, and both have structure. Your values, mental models, assumptions, self-awareness, and emotional intelligence. That's your inner operating system.
3. Consciousness is the operating system of performance. Your inner game drives your outer game far more than most leaders realize. The way you think, your beliefs, and the patterns running underneath your thoughts. Those are what determine how you respond when pressure shows up.
4. To achieve higher performance, you have to be restructured. I'm not talking about your core values or ethics, those should already be solid in any mature leader. What has to change is the level of complexity your inner operating system can handle without breaking down.
Think of it this way. If you've trained your body to comfortably lift thirty pounds and the situation in front of you requires sixty, you have a problem. Your back, your arms, your form — none of it has been built for that load. You can hurt yourself trying. Or you simply can't lift it at all.
The weight is the complexity of the world outside you. The strength and form to lift it are your inner operating system. When the load exceeds the capacity, something gives.
The cleanest way I know to say it: the maturity of your inner operating system has to match or exceed the complexity of the challenges you're facing. When the complexity outside exceeds the capacity inside, you don't just struggle tactically. You struggle at the level of judgment, clarity, and direction.
Here's the part nobody wants to say out loud: most leaders never make the move. They get to a certain level and keep running the same inner operating system at higher and higher speeds, wondering why the outputs aren't keeping up.
That's the part of volatility nobody talks about. The problem isn't only outside. The gap is also inside.
Two Things You Can Do
So what do you do about it?
Two answers. The first is tactical — useful right now, but more of a bandage. The second is the deeper fix — slower to build, but it's the one that actually lasts.
Start with the tactical answer: build margin. If you're running with tight margins and a shock hits, you're not going to be able to manage the change. You'll be trying to survive it.
For predictable volatility, like a seasonal swing you've seen before, you can plan for it. A 20–30% cash buffer over what you needed last year gives you room to absorb a surprise. But when volatility is both high and unpredictable, tighter planning doesn't replace margin. The math doesn't work.
The deeper fix, and this is what the rest of this series is ultimately about, is that you have to invest in your leadership. Not just consume more leadership content.
Most of us, at some point, have believed that if we just keep reading books on leadership and business, the knowledge will rattle around inside our brain until the moment we need it, and then we'll pull it out and execute. When you say it out loud, it's almost embarrassing. Either you'd never actually do that, or you're laughing because you know you've already fallen into that trap. I know I have.
Real growth doesn't work that way. It's done with feedback, with practice, almost always in community, and usually with a coach or advisor who can see what you can't see from the inside.
The leaders I've watched successfully navigate genuinely hard seasons aren't the ones with the biggest libraries. They're the ones who did the inside work, either before the season got hard, or with the humility to stop and do it mid-storm. The second takes more guts. Most of us start there, and grow toward the first.
Are You Experiencing Volatility Right Now?
Before we wrap, I want to ask you a favor.
Does this resonate? Are you experiencing volatility right now — in yourself, in your business, in the people around you?
Is it showing up in your pipeline, your costs, your planning, your people, somewhere else? Did this conversation help you identify something you hadn't seen, or confirm what you were already sensing?
This issue is built around the first letter of VUCA. The first of four forces affecting the world today. I'd like your feedback on whether I'm articulating it well enough that you recognize it. Is it useful? Does it bring fresh clarity? Or do you think I'm out in left field?
I really want to know. I read every response, and your answers are going to help me shape the next three issues.
Next issue: Uncertainty. Related to volatility, but different in ways that matter.
If this was helpful to you, email me and let me know.
Until next time,
Keep learning.
Keep growing.
And God bless,
Michael
