Courage Camp: 5 Weeks to Courageousness

"Jonathan, how much is fear costing you?"

My mentor asked me this over lunch in 2018. I immediately paused for what felt like a 30-minute TV episode. My mind raced through all the moments fear had held me back...the meetings where I stayed silent, the investments I passed on, the startup ideas that never saw the light of day.

My mentor snapped me out of my trance by leaning across the table and saying, "You have the intelligence and talent, but you also have a saboteur." My jaw tightened in conviction. No one had ever told me this before, but I knew there was truth to what he was saying. He then added, "You're paralyzed by fear, and it’s robbing you of realizing your true potential. You're playing too small." I knew he was right. Fear was standing in the way of me maximizing my potential. Fear of failure. Fear of judgment. Fear of embarrassment. Fear of making the wrong decision. And it was costing me—more than I’d ever realized. Not just in terms of business success but in peace of mind and self-confidence. I watched others with no more ability than me getting ahead simply because they weren’t being owned by fear. Have you ever felt this way, too?

PayPal co-founder and billionaire investor Peter Thiel said it best: “Courage is in far shorter supply than genius.” In life and in business, fortune favors the bold. IQ only goes so far, and after a certain point, it can become counterproductive, leading to over-thinking and inaction. The courage to act is what separates the thinkers from the doers.

I left that lunch committed to looking at fear differently. Fear wasn't just a benevolent friend there to protect me; it had become an overprotective impediment, costing me more than it was benefitting me.

My extensive research into the science and psychology of fear revealed two foundational fallacies people have about courage that keep them playing smaller than they're capable of:

Fallacy #1: Most people think of courage as something you’re either born with or not—like height. They tell themselves things like, "I'm just not a courageous person." But in reality, courage is like a muscle. You can build it through deliberate practice. And if you don’t use it, you lose it. Courage, like cowardice, is also contagious. Our families, friends, industry, profession, and colleagues all impact our levels of courage.

Fallacy #2: Courage means the absence of fear. In reality, courage isn't the absence of fear—it’s the willingness to take action in the face of fear. It's learning to "do it scared." Dr. Robert Biswas-Diener, PhD, a psychologist and researcher, covers this in his book The Courage Quotient. It details how courage can be measured just like an IQ score and increased with deliberate effort.

Over the next five years, I set out to develop my courage muscle by "doing it scared"—taking action even when I felt fear. I learned to get comfortable with being uncomfortable. I ran with the bulls, went skydiving, and performed stand-up comedy, all while feeling fear but not letting it stop me.

Through trial, error, and self-reflection, I developed my own frameworks and tactics that allowed me to consistently move forward despite my doubts.

This is why I created Courage Camp: to help other talented over-thinkers reframe how they think about fear, risk, and opportunity, so they can redefine their relationship with fear and move forward with more conviction and confidence. In Courage Camp, you'll actively practice reframing fear, become more self-aware, and strategically embrace risk through structured exercises and group discussions.

Jeff Bezos said, "If you're not willing to take bold risks, you're going to have to settle for a life far smaller than you are capable of living. Courage is the key." I couldn’t agree more. I refuse to settle for a life smaller than the one I’m capable of living.

If you're committed to this as well, I'd love to help you begin growing your courage muscle. I'm proud of my courageous actions, and I know you will be, too.