ISSUE #019 | THE LEADERSHIP CONTRARIAN
Welcome back.
Do you ever feel like what people call random isn’t really random… and that history seems to repeat itself—but we don’t quite see the pattern while we’re in it?
There’s a pattern in history that shows up every 80 to 100 years, and it has a lot to say about what’s happening in our world right now.
And it’s not theoretical. It’s history, and it can help your leadership and your business right away.
Over the next three weeks, I want to do something a little different. Instead of focusing on one isolated leadership idea, we’re going to zoom out and look at a different mega trend each week.
Because there are bigger forces at play right now. Forces that are shaping your business, your team, and your decisions whether you’re paying attention to them or not.
This week, I’ll start with the first of three major trends.
And I don’t say this lightly:
If you miss what’s happening underneath the surface right now, you’ll keep trying to lead today’s world with yesterday’s assumptions.
Let’s Put This In Context.
By the 1840s, the Industrial Revolution was reshaping everything. Moving economies from farms to factories almost overnight.
Then in the 1940’s, the world was coming out of World War II. Entire industries were rebuilt, global power shifted, and millions of people had to relearn how to live and work.
It felt like a fresh start.
Now, eighty years later… we’re in another kind of reset.
Not identical. But familiar in a deeper way.
Because throughout history, there’s been a pattern, an 80 to 100-year cycle that quietly reshapes economies, institutions, leadership, and culture.
Most people don’t see it while they’re in it.
But it explains why certain seasons feel stable… and others feel like everything is shifting at once.
We’re in one of those shifting seasons right now.
Before we talk about the cycle itself, let’s talk about what you’re probably already experiencing.
Because this isn’t theoretical.
It’s showing up in your business, your team, and in your own leadership in ways that are hard to fully explain, but easy to feel.
Things that used to work don’t seem to work the same way anymore. Strategies that felt solid a few years ago now feel like they have a shorter shelf life than you expected.
In fact, one of my friends who has owned a successful marketing firm for over 30 years, stopped me at Costco the other day.
We were just catching up, talking about business, life… the usual.
And at one point he paused and said,
“You know what? Business is going okay… but it’s just a lot harder to make a buck now than it used to be.”
He’s not failing. He’s not doing anything wrong.
But something has shifted.
And if you’ve been leading for any length of time, you’ve probably felt it too.
It’s not just that things are changing. It’s that they’re changing faster, and with more moving parts than we’re used to managing.
You have more variables to consider. More consequences to think through. And less certainty about which decisions will actually work out the way you expect.
At the same time, the pace hasn’t slowed down, it’s accelerated.
Technology is evolving in real time; faster than most people can keep up with. AI isn’t coming someday… it’s already reshaping how work gets done today, how value is created, and what roles even matter anymore.
And underneath all of that, your people feel it too.
There’s more uncertainty in the room. More quiet pressure. More questions that don’t have clean answers yet.
And whether it’s said out loud or not, they’re looking to you for something steady.
Let’s identify what’s actually going on here.
When volatility and complexity increase, it drives uncertainty and ambiguity about what’s actually going to work.
And when that happens, the old playbooks start to break.
The reality is, what got you here won’t get you there. Not in a season like this.
Leadership is getting more complex… whether we’re ready for it or not.
So what is this cycle we’re talking about?
At a high level, there’s a pattern that tends to show up about every 80 to 100 years.
Here’s what happens.
Every one of these cycles starts with a generation of people going through a period where everything gets disrupted.
Think about my grandparents’ generation.
They lived through the Great Depression… and then World War II.
The economy collapsed. The world went to war. And when it was over, people had to figure out how to rebuild almost everything. How to work, how to lead, how to organize life again.
Out of that kind of disruption, new systems get built. New institutions. New ways of doing business. New ways of leading.
And for a while, those systems work really well.
The 1950s are a good example.
The world settled down. Families were building their lives again, businesses were growing, and there was a sense that things just worked the way they were supposed to.
The building of suburbia is a great example of that. Rows of similar houses, driveways, lawns, and neighborhoods that all looked and felt the same. It was efficient, structured, and orderly.
Things made sense.
But over time, things started to shift.
By the 1960s and 70s, they started to feel more social tension. Culture’s changing. Expectations changing. And life just kept getting more complex, and less predictable.
Everything was still working… but you could tell something’s different.
And then you move into the decades after that.
Growth, expansion, technology, globalization.
For many of us, that’s the world we grew up in. A world where things weren’t perfect, but they were understandable. You could make decisions and feel like you had a decent shot at being right.
Until you couldn’t.
Because eventually, the system reaches a point where it doesn’t hold together the same way anymore. And another period of disruption begins.
That’s the cycle.
It’s not exact. It doesn’t run on a perfect clock. But it happens often enough that when you step back… you start to see it.
And that matters for two reasons.
First, it helps you understand where you are.
It gives you context for what you’re experiencing right now—why things feel more unstable, more complex, and harder to predict than they used to.
Second, it becomes a tool.
A way to step back and get perspective.
Because when you can see the pattern, you’re not just reacting to what’s in front of you. You’ve got a little distance. A little clarity.
It changes how you think, how you make decisions, and how you look at your team and your business.
You start asking better questions. You start thinking longer-term. You start leading with more intention instead of just reacting to pressure.
And this is where it matters for you as a leader.
Because when you’re inside one of these shifts, it doesn’t feel like a “cycle.”
It just feels like things aren’t working the way they used to.
It feels like more pressure. More uncertainty. More complexity without a clear playbook.
But when you understand the larger 80-100 year cycle, something shifts.
You stop thinking, “This is just a tough season.”
And you start recognizing it as a transition—
a major transition… a once-in-a-hundred-years kind of transition.
From one way of operating… to another.
That doesn’t make it easier.
But it does make it clearer.
It gives you context.
It’s like going from a flat, 2D picture to suddenly seeing the whole thing in 3D.
You’re not just reacting anymore. You can actually see what’s happening.
And that changes how you lead.
Because leaders who can see the shift make different decisions. They invest differently. They build differently. They lead differently, not because they’re guessing better, but because they understand the season they’re in.
And by the way—
That's what wisdom is.
It’s really about making the right decisions based on the season you’re in.
So what does this actually mean for you?
If we’re in one of these major transitions, then two shifts are happening at the same time.
The first is external.
The world itself is changing faster than most people are prepared for.
We’re already seeing it.
AI isn’t something coming five years from now. It’s already reshaping how work gets done today.
What used to take hours now takes minutes. What used to require a team can now be done by one person with the right tools.
Entire roles are shifting. Entire industries are being redefined in real time.
And this is where most people underestimate what’s happening.
They think this is just another wave of technology.
It’s not.
This is exponential.
Which means the pace of change doesn’t just increase… it accelerates.
The rules didn’t disappear… they just stopped working the same way.
And that creates a gap between how fast the world is changing and how fast people are adapting.
The second shift happening at the same time is an internal shift. If the world is getting more complex, then leadership has to get more complex too.
In a world like this, where things are moving faster and less predictably, you don’t always have the luxury of waiting until everything is clear. The window to make decisions is often shorter than you want it to be. And the answer isn’t to try and slow everything down. You can’t.
The answer is to grow your capacity. To think at a higher level, to handle more complexity, and to see more, faster, and more clearly. Because when your capacity grows, you don’t need as much time to get to clarity. You can move faster, without becoming reactive.
That’s what this season demands: leaders who are stretching how they think, how they see systems, and how they make sense of what’s happening around them. The goal isn’t to avoid complexity. It’s to become the kind of leader who can handle it.
This means something most people don’t like: you don’t get the luxury of clarity first. You have to lead without it.
That doesn’t mean you wait. It means you make the best decision you can with what you have and move forward.
Over time, the goal isn’t to eliminate that tension. It’s to get better at navigating it—to think more clearly and decide more wisely, even when things aren’t fully clear.
Because in a season like this, that’s the job.
This is why understanding the cycle matters.
Because this isn’t just a hard season. It’s not just a tough market or a strange moment in business.
You’re leading through a transition, a shift that only happens every 80 to 100 years.
The kind of shift that reshapes how people work, how businesses operate, and how leadership actually functions.
And whether you realize it or not, you’re already in it.
So the question becomes: How are you going to lead in it?
Some leaders try to hold on to what used to work. They preserve it, extend it, protect it, and for a while, that can look like stability.
But over time, it turns into resistance.
And eventually, irrelevance.
Other leaders recognize what’s happening.
They don’t panic. They don’t rush.
Instead, they grow. They adapt. They expand how they think, how they lead, and how they make decisions.
Ultimately, they understand something most people miss:
You don’t move through a transition like this by holding on to the past. You move through it by becoming the kind of leader change requires.
That’s not automatic.
It’s a choice.
And in a once-in-a-hundred-year transition like this, it’s a choice that matters more than most.
So here’s the question:
Are you trying to protect what used to work… or are you becoming the leader this season actually requires?
If this was helpful to you, email me and let me know.
Until next time,
Keep learning.
Keep growing.
And God bless,
Michael