[Issue #045] The Wind Has Changed. Have You?

The Leadership Contrarian

October 31, 2026•9 min read

I recently had a conversation with a young couple Kathryn and I coach.

They're raising several kids, running a business together, and working hard to build something meaningful.

Like many business owners, they've experienced some significant ups and downs over the last couple of years.

And when things get difficult, they naturally start asking questions.

What are we doing wrong? What are we missing? What can we change? What levers can we pull to get things moving again?

Those are good questions. They're questions every responsible business owner should ask.

But during our conversation, I realized there was another question we needed to consider first:

Have you ever done this before under these economic conditions?

It turns out they hadn't.

They'd never led a business through a prolonged economic downturn. They hadn't navigated one as a married couple responsible for a company, employees, and a house full of children.

And that matters more than you might think.

When the wind changes

Imagine riding your bicycle down a beautiful country road.

The sun is shining. The wind is at your back. You're pedaling along, covering ground, making great time, and feeling pretty good about yourself.

Then you turn around.

Now you're riding into a strong headwind.

You're pedaling harder than before, but you're barely making progress.

You're exhausted. You're frustrated.

And if you aren't paying attention to the wind, you might start wondering what's wrong with you.

Did I get out of shape? Am I doing something wrong? Why isn't this working anymore?

Sometimes you're not doing anything wrong. The conditions have simply changed.

That's context.

And context matters enormously, especially when you're leading a business.

A little historical perspective

Recently, I found myself thinking about the economic challenges we've experienced over the years.

I wondered whether there had ever been a generation that escaped significant economic and financial turmoil.

The more I looked into history, the more I was reminded that difficult economic seasons aren't unusual. They're a recurring part of life, and every generation experiences them.

In fact, when I looked back over the last 500 years, I couldn't find a generation that had avoided major economic hardship.

So I found myself asking why it's so hard for people to remember that difficult seasons are normal and that we have to approach these seasons differently.

Which led me to something even more interesting.

The longest economic expansion in recorded U.S. history lasted 128 months, from June 2009 to February 2020.

That's just over ten and a half years.

The previous record was exactly 10 years, or 120 months, from March 1991 to March 2001.

Think about that.

If you're 40 years old today, you were approximately 23 when the Great Recession ended in 2009.

You might have been finishing college, starting your career, or just beginning to build your adult life.

neon caution sign representing economic downturn

You may never have experienced a prolonged economic downturn as anything other than a student or young adult. And you probably never experienced it while owning a business, supporting a family, employing people, and making payroll.

For some entrepreneurs today, nearly their entire business experience has taken place during what most of us would call "Good Times."

They've spent much of their business lives riding with the wind at their backs.

At this point, you might be saying that COVID was a downturn, and in some ways you'd be correct.

But COVID was unusual. While many businesses suffered terribly, other industries, including e-commerce, home improvement, and delivery services, experienced extraordinary growth.

And when those conditions changed, many businesses had to adjust all over again.

All of this to say, things have changed.

And now the wind feels different.

Which reminds me of Dick Van Dyke playing Bert in Mary Poppins. Somehow, his words seem especially appropriate right now.”

“Winds in the East, mist coming in,

Like somethin' is brewin' and 'bout to begin.

Can't put me finger on what lies in store,

But I feel what's to happen all happened before."

But isn't the economy doing well?

That's part of what makes this so confusing.

Some businesses are doing exceptionally well.

Technically, we're not in a recession. But for many business owners, the tighter spending, longer sales cycles, and pressure on profitability can certainly make it feel like one.

And the headlines don't always tell the whole story.

Take the S&P 500.

According to a March 2026 report from Landmark Wealth Management, the seven largest technology-driven companies, known as the Magnificent Seven, experienced earnings growth of approximately 40% in 2024, while the other 493 companies in the index averaged just 4%.

Even the report's 2026 forecasts showed a significant difference: 26% earnings growth for the Magnificent Seven compared with 11% for the other 493 companies.

That's a huge difference.

And it's a reminder that strong overall economic numbers don't necessarily mean everyone is experiencing the same conditions.

The important thing here is to dig beneath the headlines and continue looking at the context of your own business.

That's easier said than done when running a business is already hard work and bad advice is everywhere, especially from people selling quick and easy growth.

A growing economy doesn't guarantee that your business has a tailwind.

That's why we need to pay attention to what's actually happening around us rather than simply assuming that what worked yesterday should work today.

Experience changes your perspective

Kathryn and I have been business owners for more than 24 years.

We've experienced the Great Recession, the COVID pandemic, and plenty of other challenging seasons.

And one of the gifts of having been through difficult times before is perspective.

We've learned that hard seasons come and go.

We've learned that we can survive challenges we once thought might be the death of us.

And we've learned that the things that were no-brainers in one economic environment don't necessarily work in another.

I also think about my grandparents, who lived through the Great Depression.

They were heroes to me.

They experienced extraordinary hardship, yet went on to live rich, meaningful lives well into their nineties.

Remembering their stories from the Great Depression and World War II helps me keep my own challenges in perspective.

What you're experiencing today isn't necessarily a prediction of what your future will look like.

And that brings me to something I've learned about the importance of context.

Your perspective affects more than your decisions

One of the things I've learned over the years is how important it is to pay attention to what I'm thinking, especially when circumstances are discouraging.

Our thoughts influence our emotions, and our emotions have a tremendous influence on our energy, motivation, and willingness to act.

When we start thinking that things will never get better, or that we're failing because our results aren't what they used to be, it's easy to become discouraged.

And discouragement has a way of draining the very energy and creativity we need to work through our challenges.

It can become a downward spiral.

That's why, when I find myself getting discouraged, one of the first things I try to do is step back and make sure I'm seeing the bigger picture.

I remind myself of what we've already been through, what we've learned, what's going well, and what's happening around us.

Not to pretend the challenges aren't real, but to make sure I'm interpreting them correctly.

Because when I change how I'm thinking about a situation, it often changes how I'm feeling about it.

And that helps me recover the motivation, energy, and even the joy I need to keep moving forward.

Sometimes the first thing you need to change isn't your circumstances. It's how you're interpreting them.

But there's another important lesson here.

Perspective isn't enough

I have a friend who helped grow a company from approximately $4 million to $40 million over about 14 years.

That's impressive by any standard.

He was a talented leader who helped build a successful organization.

But he'll be the first to acknowledge that the company was also operating in an industry experiencing tremendous growth.

Demand was strong. Prices were rising. Customers were doing well.

He understood something important.

When the wind is at your back, good leadership can produce extraordinary results, but you can't take credit for all of the success.

And when you're riding into the wind, you need more than the same effort and the same strategy.

You need to adapt.

And that's what I want to encourage you to do.

If sales cycles are getting longer, your sales process may need to change.

If customers are more cautious with their money, you may need to communicate value differently.

If your margins are being squeezed, you may need to rethink your pricing, expenses, or operations.

If you're measuring your sales team against close rates established during a much stronger market, you may need to reconsider what's realistic and whether they have the tools they need to succeed.

If your goals were established during the boom years of internet businesses, Instagram millionaires, and The 4-Hour Workweek, you may need to recalibrate your expectations.

And if you're exhausted from working harder and harder without seeing the results you once enjoyed, you may need to reconsider how you're approaching the work.

You are not alone in facing these challenges. But that doesn't mean every problem is caused by the economy.

Sometimes we need to change our expectations. Sometimes we need to change our strategies. And sometimes we need to improve our own leadership. (sidenote: all of these things fall under leadership if that wasn’t obvious.)

The challenge is figuring out which is which.

But don't be confused by what I'm saying. Context isn't an excuse to stop making progress. It's information that helps you make wiser decisions.

Don't lose heart. And don't stop learning.

This is what I want you to remember.

You don't have to pretend that business isn't difficult right now.

You don't have to convince yourself that everything is wonderful when it isn't.

But you also don't need to allow difficult circumstances to rob you of your hope, joy, or motivation.

You can acknowledge reality without being defeated by it.

And you can change your approach without assuming you've failed.

That's what good leaders do.

They keep learning. They keep adjusting. They keep leading.

And they remember that there's a difference between struggling because you're doing something wrong and struggling because the conditions have changed.

Sometimes it's both.

The wisdom is knowing the difference.