From Imposter to Leader: Embracing the Journey

Have you ever felt like a fraud in a professional setting? Raised your hand during a business meeting, only to be gripped by that nagging feeling that you don’t belong there? I have. And here’s the thing: that feeling isn’t a weakness—it’s a sign you’re pushing your boundaries and challenging yourself.

A Tale of Two Worlds

Growing up just ten minutes from affluent neighborhoods, I used to drive past beautiful houses and wonder, “Who lives there? What did they do to deserve this kind of success?” Now, ironically, I live in one of those houses. But that journey? That’s where imposter syndrome began its whispers.

I was fortunate to have two loving parents, despite our financial limitations. While many of my childhood friends were heading down one path, life had different plans for me. After getting kicked out of public schools, I landed in a private school—my last option, really. That’s where everything changed.

My basketball coach became more than just an instructor; he became a mentor who taught me how to be a man. His philosophy was simple but profound: life is 99% what you make of it, 1% what you can’t control. No excuses. Just work. For the first time, I started seeing possibilities instead of limitations.

I found myself caught between two worlds. At private school, I was surrounded by kids who had things I’d never imagined. I started fitting in, learning their ways, seeing their opportunities. But back in my old neighborhood? My childhood friends said I was changing, that I wasn’t “one of them” anymore. They were right—I was changing. I felt like an imposter in both worlds: not quite fitting in with my new peers, but no longer fitting in with my old ones either.

Basketball became my ticket to college with a full scholarship. But the real game-changer? The Internet and computer programming. I discovered this whole new world of possibilities, fell in love with it, and that became my path forward. In 2014 I started KORTX. We’ve since worked with more than 350 agencies and managed over $300 million in media.

Understanding Imposter Syndrome

Imposter syndrome isn’t actually a syndrome of failure—it’s a syndrome of success. You don’t feel like an imposter when you’re comfortable. You feel like an imposter when you’re stretching, growing, achieving things you once thought were beyond your reach.

In the business world, it shows up in predictable but powerful ways:

• When you close a bigger deal than ever before, but worry you oversold
• When your company hits a new milestone, but you attribute it to lucky timing
• When you’re surrounded by incredible achievers and question if your success measures up

Almost every high achiever I know has felt it, and the higher they climb, the more often it shows up. Why? Because success and growth mean constantly pushing beyond your comfort zone, repeatedly doing things you’ve never done before.

Managing Imposter Syndrome

Start by naming it. That feeling of being a fraud? Call it what it is: imposter syndrome. It’s like turning on the lights and realizing the monster in the dark is just a shadow.

Then counter it with evidence. When the voice in your head says “You don’t belong here,” pull out a Reality Check List:

• Projects you’ve successfully led
• Challenges you’ve overcome
• Lives you’ve impacted through your work
• Value you’ve brought to conversations

And don’t do it alone. Find people who are willing to be real with you. When you share your struggles and respected peers share theirs, you realize it isn’t a personal failing. It’s a shared human experience.

The New Room: AI

Right now I see the same feeling in a different room. Agency owners who have spent twenty years building client relationships, running teams and making media decisions sit in a meeting about AI and think: I’m not technical enough for this. Someone younger, or someone who codes, is going to figure this out, and I’m going to be left behind.

Here’s what I’d tell them, as someone who does write code: the code is becoming the easy part. The tools write more of it every month. What they can’t do is decide which problem is worth solving, which number the client actually cares about, or when an answer is confidently wrong. That’s judgment, and you’ve been building it your whole career.

Feeling like an imposter in that room doesn’t mean you don’t belong there. It meant the same thing for me at that private school: you’re walking into a bigger room than the one you came from.

A Call to Action

As I write this post, I have two requests:

For those currently experiencing imposter syndrome:

• Meet it head-on
• Embrace the discomfort
• Seek support and connection

For those who have moved past it:

• Be the mentor you needed
• Create safe spaces for vulnerability
• Help others navigate their journey

Remember: Imposter syndrome isn’t just about feeling like you don’t belong. It’s a signal that you’re pushing boundaries, taking risks, and growing. And that’s exactly what leaders do.