October 23, 2025

Dealing with Imposter Syndrome: How I Learned to Lead Even When I Didn’t Feel ‘Ready’

Dealing with imposter syndrome? Discover how to lead with confidence and clarity even when doubt creeps in. Learn personal strategies for overcoming self-doubt and leading with purpose, inspired by Matthew Mathison’s Leadership Orbit framework.

There have been moments in my career, more than I’d like to admit when I’ve walked into a room and thought, “Do I really belong here?” It didn’t matter what I had accomplished or how prepared I was. That quiet, persistent doubt still found a way in.

That’s the thing about imposter syndrome; it doesn’t care about titles, achievements, or years of experience. It shows precisely when you’re stepping into something meaningful. And often, it happens not to undermine you, but to test how deeply you understand your purpose.

Over time, I’ve learned that dealing with imposter syndrome isn’t about eliminating the fear of being “found out.” It’s about leading anyway, showing honesty, humility, and the willingness to grow, even when you don’t feel perfectly ready.

Dealing with Imposter Syndrome: The Reality Beneath the Surface

For me, imposter syndrome never appeared in big, dramatic ways. It was subtle, a moment of hesitation before speaking, an instinct to overprepare, or a quiet need to recheck what I already knew was right.

The first time it hit me hard, I was leading a team older and more experienced than I was. On paper, everything lined up. In reality, I felt like an impostor wearing confidence that didn’t quite fit.

It took time and a few humbling experiences, to realize that everyone I admired had felt the same way at some point. They just learned to keep moving forward anyway.

That realization changed the game for me. Confidence stopped being something I waited for and started being something I built through consistent action.

Dealing with imposter syndrome became less about feeling worthy, and more about serving well.

Purpose Over Perfection

There was a season early in my leadership journey when I was preparing for one of the biggest presentations of my career. I remember pacing my office late at night, obsessing over every word, convinced that one wrong sentence could unravel everything I’d worked for.

Eventually, I stopped. I closed my notes, took a breath, and asked myself one question: “Why does this matter?”

That single question changed everything.

I realized I had been performing for approval instead of leading from purpose. The focus had shifted to me, how I sounded, how I’d be perceived when it was never about me to begin with.

When I re-centered on purpose, the fear lost its power.

That moment became a turning point, one that reminded me of what I wrote later in What Is a Leadership Philosophy? Definition, Principles, and Real Examples That Inspire: clarity of purpose is what grounds us when doubt begins to rise.

Perfection isolates you. Purpose connects you.

What Helped Me Move Forward

Even after years of leadership, I still have days when imposter syndrome tries to make itself at home. But I’ve learned a few practices that help me keep perspective when that happens.

1. I focus on contribution, not comparison.

When I stop worrying about how I measure up and start asking how I can add value, the noise quiets. Comparison drains energy; contribution restores it.

2. I lead with curiosity.

Admitting, I don’t have all the answers used to feel weakness. Now, I see it as a strength. Curiosity keeps me humble, teachable, and connected to the people around me.

3. I Keep a record of growth.

When self-doubt distorts reality, evidence grounds you. I keep notes of moments that mattered, projects that worked, people I helped, challenges I overcame. It’s not prideful. It’s a perspective.

4. I speak it out loud.

There’s power in honesty. When I’ve shared my doubts with trusted peers, the response is almost always the same: “Me too.” The shared humanity in that phrase is often enough to pull me back to the center.

What Dealing with Imposter Syndrome Taught Me About Leadership

I’ve learned that imposter syndrome doesn’t always signal a problem; it often signals growth. It means you’re stretching beyond what’s familiar, stepping into a space where your skills and courage are still catching up with your calling.

In that sense, it’s not an obstacle; it’s a teacher. It sharpens self-awareness, deepens empathy, and reminds you that leadership was never about having all the answers.

A while ago, I wrote in an Entrepreneur article that the most effective leaders are those who move with intention even when things feel uncertain. That applies here, too.

Imposter syndrome thrives in ambiguity. But when you lead clarity, about what you believe, what you value, and what you’re trying to create, you can move confidently even through doubt.

Re-Centering on Purpose

The more I reflect on this, the more I see imposter syndrome as a mirror. It forces you to confront the gap between who you think you are and who you’re becoming.

And that’s where leadership really begins, not when you feel ready, but when you choose to act despite the doubt.

Every major step in my career began with uncertainty. I didn’t have all the information, experience, or guarantee of success. But I had a purpose, and that was enough to move forward.

In Leadership Orbit, I wrote about how alignment between purpose, clarity, and courage creates sustainable momentum. Imposter syndrome loses power when your actions stay aligned with your principles.

That’s what real confidence feels like, not the absence of fear, but the presence of alignment.

Final Thoughts

If you’re dealing with imposter syndrome, know this: you’re not broken. You’re growing.

The presence of doubt doesn’t mean you don’t belong; it means you’re expanding your orbit.

Every leader, no matter how seasoned, faces moments of uncertainty. What matters is how you respond. Keep your purpose visible. Keep your perspective honest. Keep showing up.

Because leadership isn’t about feeling ready. It’s about being real and leading forward anyway.