Some of the most important decisions in our lives don’t feel important when we’re making them.

Looking back, moving to Panama was one of those decisions for me.

This week’s reflection is about why the opportunities that change our lives often arrive long before we feel ready for the change.

The Plan

More than a decade ago, I had a plan. I was going to move to Paris.

After closing my consulting firm, I had decided it was time for a completely different chapter of my life. In fact, I already had a job waiting for me there. The next chapter seemed clear.

Then I met Alan Nottingham.

Alan was starting a new company. What makes the story even more interesting is that moving to Panama wasn’t originally part of the plan. Then circumstances changed.

Suddenly, the question wasn’t whether I was moving to Paris.

The question was whether we were moving to Panama.

I still remember Alan telling me:

“If you don’t want to move to Panama, we won’t.”

Looking back, it’s remarkable how much can hinge on a single conversation. Neither of us could have known what would happen next. What the company would become. What experiences would follow. What friendships would be formed. What lessons would be learned. Or how much that decision would ultimately shape both of our lives.

I agreed to move.

And my life changed.

For the better.

At the time, Santiago de Veraguas had a population of roughly 60,000 people. I was living in Houston, a metropolitan area of more than six million people. To say it was a change would be an understatement.

Love is a funny thing.

One moment you’re planning a future in Paris. The next you’re packing for a town of 60,000 people in rural Panama and helping launch a company that doesn’t yet know what it will become.

What I Thought I Was Choosing

What fascinates me looking back is how little I understood about the decision I was making.

I thought I was choosing between two locations. Paris or Panama. What I was actually choosing was a future.
I just didn’t know it yet.

What followed were years of experiences I never could have predicted. Building operations across multiple countries. Forming friendships on multiple continents. Learning leadership lessons that no classroom could have taught. And building a life with Alan that began with a decision neither of us could fully understand at the time.

There would be challenges I couldn’t yet see. Lessons that would reshape how I viewed leadership, culture, and people. There was no way to know what that decision would ultimately mean.

And that realization has stayed with me because it exposed a myth that I think many leaders and professionals believe.

The myth is that one day we will finally feel ready.

Ready for the promotion. Ready for the move. Ready to lead. Ready to make the change.

We convince ourselves that if we gather a little more information, gain a little more experience, or build a little more confidence, then we’ll finally be ready to move forward.

But life rarely works that way.

Many of the opportunities that shape our lives arrive long before we feel ready for them.

The leadership role. The career change. The move across the country, or across the world. The chance to build something that doesn’t yet exist. The relationship that changes everything.

What I’ve learned is that some of the most important decisions we will ever make come with incomplete information.

Not because we’re careless. Not because we’re reckless. But because the future has a way of withholding its secrets until we’re actually living it.

At the time, I wasn’t choosing a decade of leadership lessons. I wasn’t choosing lifelong friendships across multiple continents. I wasn’t choosing experiences that would fundamentally change how I viewed leadership, culture, relationships, and people.

I was simply making the best decision I could with the information I had.

Looking back, that may be the real definition of being ready.

Not having every answer. Not eliminating every risk. Not knowing how the story ends. Just having the courage to move forward when the next chapter hasn’t been written yet.

The Certainty We Never Get

A thoughtful comment on this week’s post asked:

“Does experience make us more willing to act without certainty, or simply more comfortable with the risks that come with it?”

Looking back, I think the answer is a little bit of both.

When I moved to Panama, I assumed experience would eventually eliminate uncertainty. I thought there would come a point where I would know enough, see enough, and learn enough that the surprises would stop.

That point never arrived.

Instead, what changed was my relationship with uncertainty. I became more comfortable making decisions without having every answer. I became more confident in my ability to adapt when things didn’t go according to plan. And perhaps most importantly,

I stopped viewing uncertainty as evidence that I wasn’t ready.

One of the lessons Panama taught me is that readiness and certainty are not the same thing.

You can be ready and still be surprised. You can be experienced and still make mistakes. You can do everything right and still encounter situations you never anticipated.

What Experience Actually Teaches Us

Some of the most valuable lessons I’ve learned came from situations I never would have predicted.

Early in my time in Panama, I brought a client to the country during Carnavales, one of the busiest holidays of the year. Everything seemed under control.

Until I arrived and discovered that the hotel had canceled the reservation after being unable to reach me to reconfirm it.

No room. No backup plan. And a client standing next to me.

At the time, I viewed experiences like that as evidence that I still had more to learn.

Looking back, I realize they were evidence that learning never stops.

The surprises didn’t disappear as I gained experience.

The surprises simply changed.

And that’s true for leadership as well.

Early in our careers, we often assume experienced leaders possess a level of certainty that we don’t yet have. We imagine they know exactly what to do. Exactly what will happen. Exactly how decisions will unfold.

The reality is often much different.

Experience doesn’t remove uncertainty.

It teaches us how to move forward despite it.

When Self-Doubt Becomes the Obstacle

For some people, the barrier isn’t uncertainty.

It’s self-doubt.

Over the years, I have written and spoken about imposter syndrome and the feeling that we are somehow less qualified, less capable, or less prepared than everyone around us.

The irony is that many of the opportunities we admire in hindsight were accepted long before we felt ready for them.

The promotion comes before we feel like a leader. The business begins before we feel like an entrepreneur. The keynote invitation arrives before we feel like an expert. The move happens before we feel settled. The opportunity appears before we feel prepared.

Perhaps one of the greatest misconceptions in leadership is believing that confidence comes first.

More often, confidence is the result of doing something we were not completely certain we could do.

It is built through action.

Not before it.

The Wrong Question

For much of my career, I believed readiness was a destination.

One day I would have enough experience. Enough knowledge. Enough confidence. Enough certainty.

Then I would be ready.

What I have come to realize is that readiness is not a destination at all.

At some point, every leader faces situations where there is no additional information that will provide complete certainty.

No amount of planning will tell you exactly how a new role will unfold. No spreadsheet will predict every challenge of a new business. No amount of research will tell you exactly how a move, a relationship, or a major life decision will change you.

Eventually, the question stops being:

“Do I have enough information?”

And becomes:

“Am I willing to move forward without knowing how the story ends?”

What Panama Taught Me

Looking back, I wasn’t ready for what Panama would teach me.

I wasn’t ready to lead across cultures. I wasn’t ready for many of the challenges that would come. And I certainly wasn’t ready for many of the opportunities.

But I was willing to learn.

In hindsight, that mattered far more than feeling fully ready.

If I had waited until I felt completely certain, I never would have gone.

Some of the most meaningful friendships, experiences, opportunities, and lessons of my life would never have happened.

The older I get, the more convinced I become that confidence is often built in reverse.

We take the step.

We figure it out.

Then we look back and realize we were capable all along.

The question is not whether you’re ready.

The question is whether you’re willing to begin.

 

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Closing Reflection

What opportunity, decision, or change have you been postponing because you don’t feel completely ready?

What is one decision that changed the course of your life, even though you couldn’t fully see where it would lead at the time?

If these reflections resonate with your leadership journey, I invite you to subscribe and join me each week for The Hammer Principles.