Taylor Sheridan may have unintentionally created one of the better leadership case studies of our time as he explored the Yellowstone series.

His stories span more than 150 years of American history. 1883 follows settlers moving west in search of opportunity. 1923 chronicles a family fighting to survive economic hardship and social change. Yellowstone centers on preserving what previous generations built. Dutton Ranch appears poised to tackle succession, adaptation, and what comes next.

The characters change.

The technology changes.

The threats change.

The challenge remains.

Every generation is trying to navigate uncertainty.

Watching these series unfold, I’m reminded that the pioneers heading west did not have an opportunity problem. They had a journey problem. The land was there. The opportunity was there. The challenge was surviving the trip.

Every day brought a new decision: when to move, when to wait, what supplies to conserve, which river crossing looked safe, and who could be trusted. Success rarely belonged to those with the best map. It belonged to those who exercised the best judgment.

The Oregon Trail never really ended.
We simply renamed the terrain.

The Constraint Keeps Moving

History is often shaped by a dominant constraint.

In 1883, the challenge was survival.

Food. Weather. Disease. Distance.

During World War II, the challenge became production. America didn’t prevail because it had a few better ideas. It prevailed because it could build ships, aircraft, tanks, and ammunition at a pace its adversaries could not match.

During the Cold War, the constraint shifted again. Technology mattered, but the larger contest became economic endurance. Both sides entered an arms race that neither could ignore, but ultimately one economy could sustain the burden while the other could not.

Then came the modern acquisition era.

PPBE was designed for a manufacturing world where information moved slowly and major decisions unfolded over years. The challenge became prioritization. Not every idea could be funded. Not every requirement could survive.

Today,  we are entering another transition.

Information is abundant. Analysis is becoming abundant.
AI is reducing the cost of accessing expertise.

The constraint is moving again.

The leaders who succeed are rarely the ones solving yesterday’s problem.

They’re the ones who recognize the new constraint before everyone else.

Ukraine Changed the Question

One of the most remarkable stories of the last several years isn’t really about technology.

It’s about adaptation.

When Russia invaded Ukraine, many experts predicted the war would be over in weeks. We are now years into a conflict that has repeatedly defied expectations.

Ukraine’s achievement is larger than its success against the Russian Navy.

It has consistently found ways to impose costs on a larger adversary by changing the nature of the competition. Commercial technology, drones, distributed logistics, civilian innovation, intelligence integration, and unconventional thinking have repeatedly altered the battlefield.

The lesson isn’t that drones are the future.

The lesson is that Ukraine stopped accepting the game being offered.

Rather than asking, “How do we match Russia?” it repeatedly asked, “How do we create advantages with the tools we have?”

Iran has followed a similar logic for years. Rather than competing platform for platform against larger militaries, it invested in asymmetric capabilities, proxies, drones, missiles, and influence networks that create strategic dilemmas at a fraction of the cost.

Whether one agrees with their objectives is beside the point.

The lesson is that sophisticated competitors often succeed by exploiting assumptions.

Bridges, Not Destinations

I suspect we’re making a similar mistake in business today. Many leaders talk about AI and autonomy as though they are destinations. History suggests they are more likely bridges. The settlers of 1883 did not cross the country because of wagons. The wagon was simply the technology that helped them reach the next river crossing. AI may prove to be much the same. The difference is speed.

Unlike previous technology cycles,
AI is evolving at an extraordinary pace.
Waiting for a clear winner to emerge is not a strategy.
The companies learning today will outperform
the companies studying today.

The Alliances Nobody Expected

One reason judgment remains valuable is that second- and third-order effects are notoriously difficult to predict.

Most of us can see AI is coming fast.

Most of us can see and even understand acquisition reform.

Most of us can see and feel budget pressure.

What’s harder to see are the consequences those forces create.

Around the world, new partnerships are emerging. Nations are rethinking supply chains. New trade routes are being explored. Critical mineral agreements are reshaping industrial relationships. Technology partnerships are forming between countries and companies that would have seemed unlikely only a few years ago.

Recent cooperation between Saudi Arabia and the UAE is one example.

It won’t be the last.

The most important developments of the next decade may not be the technologies themselves.

They may be the alliances, business models, investment flows, and partnerships those technologies make possible.

The map is changing.  Are you updating your mapping software? Or are you studying the old map?

Looking Beyond the Next Election

Washington often struggles to see beyond the next election cycle. Many companies struggle to see beyond the next RFP or Continuing Resolution. A few are looking toward the next administration. Very few are looking ten years ahead. That’s understandable. Ten-year predictions are usually wrong.

The value of looking farther out is not accuracy. It’s perspective.

Ten years from now, AI will likely seem ordinary. Autonomous systems will likely seem ordinary. Some of today’s acquisition reforms will survive. Others will be replaced. Many of today’s headlines will be forgotten. I’m old enough to remember Word Perfect, Visicalc, and Fortran.

Less than ten years ago, coding offered vibrant career options. Today, not so much.

The current cast of reformers will move on.

New leaders will arrive with new priorities.

Some of today’s celebrated initiatives will disappear.

Others will quietly become institutionalized.

The names will change.

The organizational charts will change.

The technologies will change.

The need for judgment will not.

Weatherproofing the Wagon

One of the biggest mistakes leaders make is confusing awareness with control.

You should absolutely understand the broader environment. You should pay attention to AI, geopolitics, budget pressures, and changing acquisition strategies.

But you should not confuse awareness with influence.

Admiral McRaven often reminds young Navy SEAL candidates that the challenge is not the mountain. The challenge is taking the next single step.

The same is true in business.

Many leadership teams spend enormous energy discussing issues that sit well outside their lifelines. Election outcomes, future administrations, geopolitical scenarios, and technology predictions all have value as context.

They rarely determine what happens inside your company next quarter.

The Oregon Trail pioneers could not control the weather, river levels, disease, or the actions of others.

Business leaders face similar realities.

You can’t control:

• How quickly technology evolves
• Elections
• Acquisition reform
• Geopolitical realignments

What you can control is the condition of your wagon:

• Building customer relationships before you need them.
• Creating multiple paths to revenue.
• Developing partnerships before conditions deteriorate.
• Experimenting with emerging technologies before competitors do.
• Investing in people capable of exercising judgment when conditions change.

The pioneers who reached Oregon did not have perfect visibility.

They didn’t know where every storm would appear or which crossings would prove dangerous.

What they did know was that every day required preparation, adaptation, and judgment.

The same remains true for business leaders today.

You don’t need to see the entire trail.
You need to see the next crossing.

And you need to keep your wagon moving while everyone else is still arguing about the weather.

What Am I Reading?

Essentialism by Greg McKeown. I’m late to this one as the book was written in 2011. The core idea is straightforward: if everything is important, nothing is important.

What I appreciate about the book is not that the ideas are new. Most executives have encountered versions of these concepts before. The value is that McKeown assembles them into a single, practical framework.

As I read it, I found myself reflecting on conversations I have with CEOs. Many strategy discussions are less about what to do and more about what to stop doing. Less about adding another initiative and more about identifying what is truly essential.

I’ve always been reasonably good at saying no—often without using the word no—as a way to protect time and improve client outcomes. This book reminded me that simplicity is not a lack of ambition. It’s often the discipline required to achieve it.

Some questions it draws out of the reader:

• What can only you do?
• What are you doing that someone else should be doing?
• Which activities produce disproportionate outcomes?
• What are you saying yes to that should probably be a no?
• If resources were cut in half tomorrow, what would remain essential?

Most leaders don’t have a shortage of opportunities. They have a shortage of focus.

That’s what makes Essentialism worth revisiting.