The Fear of Freedom: What Holds Us Back from Becoming Who We’re Meant to Be

I’ve been thinking a lot about fear lately, not the kind that shows up when you hear something go bump in the night, but the kind that creeps in when you’re right on the edge of something new, something freeing, something real. 

When Paulo Freire wrote Pedagogy of the Oppressed, he wasn’t just talking about education in a classroom. He was talking about how we see ourselves in the world. How systems, political, economic, educational, condition us to believe that staying the same is safer than changing. That comfort, even if it’s uncomfortable, is better than chaos. He talks about the fear of freedom, and man, that hit me like a punch to the chest. 

Because here’s the thing: we say we want change. We post about it. We pray on it. We dream about it late at night when the weight of it all gets heavy. But when it comes time to actually do the thing, leave the job, restructure the business, shift your leadership style, start from scratch, most of us freeze. 

Why? 

Because change requires replacement. You can’t pull out one system without replacing it with another. You can’t unlearn something without choosing to learn something new in its place. You can’t call yourself free unless you’re ready to take full responsibility for what that freedom demands.

And that’s terrifying. 

The Comfortable Cage 

Let me tell you something from experience. I’ve been a leader for over two decades. I’ve worked in government, led a behavioral health agency through storm after storm, mentored youth, started businesses, shut some down, rebuilt from the ground up. I know

what it’s like to want out of the system, to feel that something’s broken, but to hesitate when it comes time to fix it. Because what if your fix doesn’t work? What if people walk away? What if you lose it all? 

But what I’ve learned is that clarity doesn’t come before the leap. It comes after. You’ve got to jump, and then learn to build the wings on the way down. 

Entrepreneurship, leadership, even self-discovery, they all share this one brutal truth: You must leave the illusion of certainty behind. 

Most people don’t fear failure. They fear freedom. They fear the moment they can no longer blame someone else. They fear becoming their own authority, their own safety net, their own architect. And Paulo Freire knew that. He said: 

"Freedom is acquired by conquest, not by gift." 

Reconstructing the System: In Business and in Life 

Running a business is a daily lesson in courage. Especially if, like me, you come from a community where survival was the priority, not risk-taking, not scaling, not quitting a good thing to chase a maybe. 

When I first stepped into entrepreneurship, I thought it would be about strategy. Turns out, it was about identity. Every business decision forced me to confront the systems I had internalized: scarcity, perfectionism, fear of being “too much” or “not enough.” And restructuring a business? That’s next-level. It’s not just paperwork. It’s shedding skin. 

You have to ask yourself questions you’re not always ready to answer: 

What am I holding onto out of fear, not function? 

Who am I trying to please by staying small or silent? 

What kind of leader do I actually want to be? 

When you're raised in survival mode, you don’t just start trusting freedom. You wrestle with it. You mourn the predictability of the struggle, even when that struggle was never yours to carry in the first place. 

Leadership as Liberation 

Leadership isn’t about titles or even impact. It’s about liberation. A good leader doesn’t just make people feel seen, they help people see themselves. 

But to lead others through transformation, you have to walk through the fire first. You have to confront your fear of being misunderstood, of failing publicly, of changing your mind and letting people down. You have to unlearn what leadership was supposed to look like and redefine it in a way that feels honest to you. 

That’s where my own leadership journey keeps circling back to Freire’s words. The oppressed, he says, often fear freedom because it means rejecting the image the oppressor created of them. For me, that’s looked like rejecting the narrative that I’m “too emotional,”

“too bold,” “too intense.” It’s looked like choosing authenticity over approval. 

And in business, it’s meant burning down systems that no longer serve us, even when they brought us this far. 

The Leap is the Work 

If you’re reading this, you’re probably sitting on the edge of a decision. Maybe you’re tired of your job. Maybe your business feels like a cage. Maybe the version of yourself you’ve been showing the world doesn’t fit anymore. 

And maybe you’re scared. 

That’s okay. 

Fear doesn’t mean you’re not ready. 

Fear means it matters. 

Let me leave you with this: the fear of freedom isn’t a flaw. It’s a crossroads. It’s the moment before the breakthrough. And if you can sit with it, like really sit with it, you’ll start to realize that the life you’ve been craving is already calling out to you. 

You just have to answer. 

And if you fall? You’ll figure it out. We always do. 

Final Thoughts 

Pedagogy of the Oppressed might have been written decades ago, but its heartbeat is timeless. Education isn’t just what we learn in schools, it’s how we build our worldview. And freedom isn’t about breaking chains. It’s about being ready to live without them. 

So here’s to the builders. The questioners. The misfits and visionaries. The tired leaders who keep going. The entrepreneurs reinventing what success looks like. And the educators, formal or not, who are helping the next generation unlearn what never served them. 

Keep going. 

We need you.