Facing Fear: Lessons from a Maximum Security Prison Cell

Fear.

It’s a word we throw around casually—like it’s just another emotion. But the truth is, fear shapes us. It stalks our decisions, clouds our judgment, and, at its worst, can paralyze us from living fully. Right now, as I write this from a maximum-security prison in upstate New York, fear isn’t just a concept. It’s a visitor that keeps trying to sit at my table.

What Prison Taught Me About Fear

Let me back up.

What started as a civil contract dispute spiraled into a criminal conviction. It was estimated that I’d only have to serve six months. That was four years ago.

Since then, life has thrown me into a wilderness I never imagined—far from my family, far from my businesses, far from everything I built. From growing up in South Africa, to immigrating to the U.S., being broke and homeless, building a multi-million dollar company, and watching it all collapse… I’ve danced with fear in every chapter of my life. But nothing quite prepared me for being reclassified and transferred to a max security prison.

Fear Comes in Many Forms

Like the term “real estate,” fear covers a massive spectrum. There’s fear of failure. Fear of success. Fear of rejection, abandonment, humiliation. Fear of the unknown. Fear of the truth. Fear of being forgotten. And in here—fear of violence, fear of losing your sanity, and sometimes, fear of simply waking up to another day of this reality.

There’s that popular acronym: F.E.A.R. = False Evidence Appearing Real. It's catchy, sure—but it never really resonated with me. Because here’s the truth: if you feel something, it’s real. Just like love—it doesn’t need to be seen, touched, or proven on paper. Its existence is in the experience. And fear, like love, has a way of making itself known—loudly, silently, or somewhere in between. The only question is—what are you going to do with it?

How I Learned to Stand in the Ring with Fear

Imagine you’ve never been in a fight. The idea of getting punched in the face sounds terrifying. But the more time you spend in the ring, the more familiar it becomes. It doesn’t mean it stops hurting. It just stops owning you.

Fear works the same way. Every uncomfortable situation—your first breakup, your first business pitch, your first public speech, your first time walking into prison—each one is a punch to the gut. But every time you step back in the ring, you build tolerance. You become harder to shake. And eventually, the things that once terrified you become just another Tuesday.

This isn’t about being fearless. It’s about being trained.

The Mindset Shift That Changed Everything

Let me tell you about my first day at Wende Correctional Facility. I was stripped, cavity searched (not the dental kind), given a suicide blanket, shackled, and escorted to a single-man cell under blinding lights and 24/7 surveillance. I slept on a concrete slab—no clothes, no pillow, no idea what tomorrow would bring.

Fear knocked. Hard.

But instead of answering the door, I met it with something unexpected: gratitude.

I started counting what I still had. My life. My mind. My health. My kids. My limbs. I wasn’t cold. I wasn’t starving. I was breathing. And that simple act—of shifting my focus—gave me a sense of control. It gave me power. Gratitude didn’t erase the fear. But it reminded me that I’m bigger than it.

You’re Stronger Than You Think

Nelson Mandela. Malcolm X. Viktor Frankl. Paul from the Bible. Men I admire—men who faced extreme persecution—also knew what it was like to walk these corridors. And in that moment, I felt a strange, almost sacred solidarity with them. Not in greatness, but in endurance. In the refining fire of adversity.

Now, as I write this from my cell—fully clothed, with clean linens, and a bit more peace—I’m still surrounded by uncertainty. But I’m not afraid. I’ve already survived everything I was once afraid of.

Let Fear Show Up—Just Don’t Let It Drive

So if you’re out there battling fear—in your relationships, your career, your health, or just life—remember this:

• You’ve already survived your worst days.
• Fear is just part of the process.
• Gratitude is your best weapon.

Let fear show up—just don’t let it drive.

You got this.

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If this post resonated with you, I’d love to hear your story. Drop a comment below, share this post, or reach out. Let’s grow through what we go through.

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