Insights

Notes on movement, leadership, and change.

Articles and reflections from Jason Sheehy on coaching, training, and building momentum in life and business.

The Confidence Trap

We assume confidence is something we need before we act, when very often confidence is something that develops because we acted.

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Why Do Smart Executives Stay Stuck?

"The greatest obstacle to progress isn't always a lack of knowledge. Sometimes it's having too much of it."

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Your Calendar Knows More About You Than You Do

"If I wanted to understand your priorities, I probably wouldn't ask you. I'd ask to see your calendar."

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The Confidence Trap

There is a phrase we use all the time.

"When I feel more confident, I'll do it."

When I feel more confident, I'll have the conversation.

When I feel more confident, I'll apply for the position.

When I feel more confident, I'll start the business.

When I feel more confident, I'll put my hand up.

When I feel more confident, I'll make the change.

It sounds reasonable.

The problem is that we may have confidence the wrong way around.

We assume confidence is something we need before we act, when very often confidence is something that develops because we acted.

Successful People Get Stuck Too

This isn't only a problem for people at the beginning of their careers.

In fact, I think it can become an even greater challenge as we become more successful.

Success creates evidence.

You develop expertise. You establish a reputation. You become known for what you do well. People begin coming to you for answers.

There is confidence in that.

But then another opportunity appears.

A bigger role.

A different direction.

A new business.

A difficult decision.

A conversation you haven't had before.

Suddenly, you are no longer standing comfortably inside everything you already know.

And that's when hesitation can creep in.

We tell ourselves we're being sensible.

We need more information.

We need more preparation.

We need a little more certainty.

Sometimes that's true.

But sometimes we're simply waiting to feel confident.

And waiting can become a very comfortable place to hide.

The Discomfort of Growth

There is something interesting that happens whenever we step into something new.

Our awareness can increase faster than our capability.

We suddenly discover how much we don't know.

That can be confronting, particularly when we're accustomed to being competent.

I have experienced this many times throughout my own career.

Moving into a new position or taking on greater responsibility didn't mean I suddenly possessed everything required for that next level.

There was always something new to learn.

There were mistakes.

There were adjustments.

There were moments when I had to ask questions.

There were moments when I had to work things out.

And there were moments when I wondered whether I was ready.

But here's what I've learned.

Feeling uncomfortable doesn't necessarily mean you're moving in the wrong direction.

Sometimes you're uncomfortable precisely because you're moving.

You're stretching beyond the boundaries of what you already know.

The mountain has become steeper because you're climbing higher.

Confidence Needs Evidence

Think about something you are genuinely confident doing today.

Were you equally confident the first time you did it?

Probably not.

What changed?

You accumulated evidence.

You tried.

You learned.

You made mistakes.

You adjusted.

You tried again.

Eventually something that once required enormous concentration became familiar.

You had evidence that said:

"I've done this before. I can do it again."

And I believe that's one of the foundations of genuine confidence.

It isn't pretending you're capable.

It isn't positive thinking disconnected from reality.

And it certainly isn't arrogance.

It's having enough evidence from previous movement to believe you can take the next step.

Interestingly, the next step doesn't always have to be something you've done before.

Sometimes your evidence simply says:

"I've worked through things I didn't know how to do before. I can work through this too."

That's a very different kind of confidence.

Stop Rehearsing

There is another side to this.

Preparation matters.

Learning matters.

Developing capability matters.

But eventually preparation has to become execution.

There comes a moment when another course isn't the answer.

Another book isn't the answer.

Another month thinking about it isn't the answer.

You have to step forward.

Having spent part of my younger years as a dancer, I learned there is an enormous difference between rehearsal and execution.

Rehearsal is where you learn.

You get things wrong.

You receive correction.

You repeat the movement.

You refine it.

But eventually the lights come up.

The audience is there.

And you have to step onto the stage.

You don't walk onto a stage hoping nobody notices you.

You step forward and give everything you have.

Life has those moments too.

Your stage might be a boardroom.

It might be a job interview.

It might be a difficult conversation.

It might be launching something you've spent years thinking about.

It might simply be making a decision you've been postponing.

There comes a point when you need to stop rehearsing and start executing.

What Are You Waiting For?

Perhaps there is something in your life right now that you've been waiting to feel ready for.

Ask yourself:

Do I genuinely need more preparation, or am I waiting for certainty that may never come?

There is a significant difference.

You don't need to see the entire mountain before you begin climbing.

You need to see the next step.

Take it.

Learn from it.

Then take another.

Confidence doesn't always arrive and then create movement.

Sometimes movement has to come first.

And the confidence you've been waiting for is built along the way.

Keep moving.

Jason Sheehy · Founder, Life in Motion
Helping successful executives win in business without losing what matters most.

Why Do Smart Executives Stay Stuck?

"The greatest obstacle to progress isn't always a lack of knowledge. Sometimes it's having too much of it."

Over the past two decades, I've had the privilege of working with executives, business owners and senior leaders across banking, retail and corporate organisations.

One observation has followed me throughout that journey is that the smartest people in the room aren't always the ones who move. That might sound surprising. After all, intelligence, experience and expertise should make decision making easier. Yet I have often found the opposite.

The more successful people become, the more information they accumulate.

More reports.

More opinions.

More strategies.

More data.

More possible outcomes.

Instead of creating clarity, all of that information can create hesitation. We analyse, we compare and we consider every possible scenario. Eventually, movement becomes delayed by the pursuit of certainty.

It is one of the great paradoxes of leadership.

The very knowledge that helped us become successful can sometimes make us reluctant to take the next step. That doesn't mean preparation isn't valuable. It is. But there comes a point where another book, another podcast or another meeting isn't what we need.

What we need is movement.

I've coached leaders who knew exactly what they should do. They knew they needed better boundaries. They knew they needed to spend more time with family. They knew they needed to develop their people instead of solving every problem themselves.

The challenge wasn't awareness. The challenge was taking the first step.

I've come to believe that progress rarely begins with knowing more. It begins with acting on what you already know.

So here's a question worth considering this week.

What is one decision you've already made in your mind, but haven't yet made with your feet?

Sometimes the next step isn't waiting for more information.

Sometimes it's simply needing courage.

Jason Sheehy · Founder, Life in Motion
Helping successful executives win in business without losing what matters most.

Your Calendar Knows More About You Than You Do

"If I wanted to understand your priorities, I probably wouldn't ask you. I'd ask to see your calendar."

Most executives can tell you what matters most. Family, Health, Leadership, Faith, Personal growth, Relationships and Purpose. The answers usually come quickly.

Then I ask a different question.

"Does your calendar agree?"

That question often creates silence. Not because people are dishonest but because calendars don't record intentions, they record decisions. And decisions tell a story.

Every meeting you accepted.

Every commitment you made.

Every hour you protected.

Every hour you gave away.

Over time, those decisions quietly become your life. I've never met an executive who deliberately planned to neglect their health. I've never met a business owner who intentionally wanted to become disconnected from their family. Yet it happens every day. Not through one dramatic decision. Through hundreds of small ones.

One more meeting.

One more email.

One more late night.

One more promise that things will slow down next month.

Eventually, the calendar reflects urgency instead of intention. The uncomfortable truth is this. Most people don't lose what matters because they stopped caring. They lose it because they stopped protecting it.

Leadership isn't only about managing people. It's about managing attention. Because wherever your attention consistently goes, your life eventually follows.

This week, don't start by asking what needs to be added to your calendar.

Instead, ask yourself a different question.

What deserves a permanent place before everything else begins competing for it?

Sometimes the most important leadership decision you'll make isn't saying yes to another opportunity.

It's deciding what deserves to remain non-negotiable.

Jason Sheehy · Founder, Life in Motion
Helping successful executives win in business without losing what matters most.

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