At a young age, my parents often complained about how fearless I was and the trouble it caused. There were bumps, bruises, and more than a few trips to the emergency room. There was this one time (and no, not at band camp) when I climbed to the top of a dresser and jumped off, convinced I could fly. That could have been my end.
Some of my fearlessness eventually faded, but as I grew older, I continued to admire heroes who seemed immune to fear: Superman, Batman, the Terminator, firefighters, and the soldiers in war movies who charged into gunfire without hesitation. These figures inspired me to keep pushing at things I wasn’t naturally good at. I compensated for a lack of skill with a lack of fear, turning it into a personal motto. I had been fearless as a toddler. As I grew up, I tried to remain fearless by choice.
When I left grad school and joined the startup world, I initially believed founders fit that same mold. I assumed the best ones were fearless, too. Over time, I learned something different. Truly great founders, executives, athletes, celebrities, and thinkers are not reckless. They are deeply aware of what they could lose, including their companies, reputations, livelihoods, and sense of self. They feel fear acutely. What sets them apart is that they don’t let fear prevent them from doing what they believe is right or necessary. The truly great are not fearless. They are courageous.
Courage and fearlessness are often mistaken for twins, but they are closer to opposites than siblings. Fearlessness is the absence of fear. Courage requires its presence. Courage is not the elimination of anxiety or doubt. It is the discipline to act while they remain. Where fearlessness moves forward untouched, courage advances while carrying the full weight of hesitation, risk, and consequence. Courage means recognizing danger, feeling fear, and proceeding anyway because the cause is meaningful, just, or necessary. As George Washington put it, “Courage is not the absence of fear, but the ability to act in spite of it.”
Fearlessness can be accidental or even reckless. A child may be fearless simply because they don’t yet understand danger. Courage belongs to those who understand danger intimately and still refuse to let it decide for them. As Plato observed, “Courage is knowing what not to fear.” Courage is rarely loud or cinematic. More often, it is quiet, private, and unseen.
Former UFC champion Georges St-Pierre captures this distinction with unusual clarity. As his career progressed, fear didn’t fade; it intensified. What changed wasn’t the feeling, but his relationship to it. He learned to expect fear, to accept sleepless nights before fights, and to stop interpreting those sensations as signs of weakness. The suffering remained. Acceptance made it manageable. He didn’t become fearless. He became courageous.
The same pattern appears in business and technology. Steve Jobs is often remembered as supremely confident, but many of his boldest decisions were driven by fear, including the fear of mediocrity, irrelevance, and compromise. After being fired from Apple, he returned years later, knowing he could fail again, publicly and definitively. His courage wasn’t in believing that success was inevitable. He was wagering his identity and legacy again with full awareness of the risk.
Jeff Bezos has long emphasized that innovation requires stepping into the unknown with incomplete information. Amazon’s biggest bets, including AWS, Prime, and prioritizing growth over profits, were made amid deep uncertainty and internal skepticism. Bezos never hid how often experiments would fail. His courage lay in normalizing fear and failure as the cost of discovery.
Even Elon Musk, frequently labeled fearless, speaks openly about anxiety and the constant threat of collapse at Tesla and SpaceX. During periods when both companies hovered near bankruptcy, fear didn’t disappear. It sharpened the only path forward and the courage to push forward while fully expecting things might still go wrong.
Cicero wrote that “courage is not simply one of the virtues, but the form of every virtue at the testing point.” Vision, values, and conviction only matter when put to the test. It will be our courage that activates them under pressure.
Don’t seek to be fearless or to be psychologically safe from fear. Stand up to your fears with courage.
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