Courage

Courage is a strange thing – It’s choosing to do what feels right, even when it comes with a dread sense of risk or failure. Pushing through that fear is courage—but if we fail, does it become recklessness instead?

I was recently reading a great biography of Teddy Roosevelt and that’s a persona often associated with courage. But couldn’t the rough rider just as well be a reckless wreck? Calling on a war against Spain for Cuba, challenging New York elites to enforce laws concerning booze joints’ opening times. Some saw him as a hero; others called him reckless, but today we remember him as a symbol of courage. Is it simply a case of history being written by the victors?

The Rough Rider himself. A reckless adventurer or courageous leader?

So like great leaders, we too face challenges that call for courage. Sometimes, it’s hard to keep doing what needs to be done—whether I’m stuck at nearly 6 km altitude in the Bolivian mountains or facing a deadlock with a client. In moments like these, there’s often a “right” thing to do, but it feels so much easier to give up or take a shortcut. It’s like a game against the mind.

In working with clients, I often find that people focus on assigning blame instead of solving the issue. But taking total ownership—a concept Jocko Willink champions—helps to move out of finger-pointing and into real problem-solving. And of course, the first few times, it’s hard. That means you’re to blame for the fuck up and now have to suffer the consequences. So it takes a certain kind of bravado to focus on the mission even when the issue is not your fault. It allows us to move on to the real goal of the mission, which is solving issues rather than blaming people.

Phenomenal Leadership Guide

We should call on courage to spark new ideas, resolve conflicts, push ourselves as human beings to do the right thing and help humanity, even in small actions. I still sometimes see myself as a coward when I read about the bravery of officers in the Napoleonic Wars. I’d be afraid to join a war myself, especially if I wasn’t certain it was the right thing. But we need courage to overcome our “monkey brain”—the part of us that craves comfort over risk. Taking risks, doing what’s right, and accepting responsibility if we fail—these are the stories people write about, stories of both great victories and failures. And each of them involves courage, and sometimes, a bit of recklessness.

Can we improve this skill? I’m writing this roughly 12 hours before summiting Kilimanjaro. As I look at the peak, it’s clouded and seems to lie in domains not meant for humans. For some, this climb might seem courageous, even reckless. But I think the difference lies in preparation. When we’re equipped for the challenge, it doesn’t feel reckless—maybe not even courageous. But we have to try and do all kinds of activities and push ourselves. Courage isn’t just for the big moments; it’s a skill we cultivate daily. Whether we’re bungee jumping in Kyrgyzstan, going against our superiors when they’re speaking nonsense, or even asking out that girl or boy you like, every courageous act trains us to choose the harder, better path over the easier one.

Conquering challenges in your life is what it's all about.