Courage to Try, Humility to Learn

A few years ago, I had the privilege of spending a week with Richard Branson and an incredible group of entrepreneurs and change-makers on Necker Island hosted by Virgin Unite, Branson’s Foundation. It was a week filled with deep conversations, bold ideas, and a unique opportunity to spend time with with a host of visionary leaders across broad spheres of influence.

On our first evening, I had the honor of interviewing Richard about risk, resilience, and the realities of entrepreneurship.

What struck me most wasn’t just his insights on success, but his humility about failure—his willingness to acknowledge what he doesn’t do well, where he’s fallen short, and what he’s learned along the way.

It’s easy to admire those who have reached the top of the mountain, but we rarely see the countless times they stumbled on the way up. We see the highlights, the triumphs, the end results—but not the sleepless nights, the moments of doubt, the costly mistakes. And yet, it’s in those moments of struggle that success is shaped.

Branson’s perspective reinforced something I’ve explored deeply in The Courage Gap: We cannot control the outcomes of our efforts—only the effort itself. And only when our courage to risk worthy failure in pursuit of a meaningful goal is paired with the humility to learn as we go, can we continually upgrade our inputs to improve the outputs.

The most successful leaders are not those who avoid failure, but those who embrace it as part of the learning process. Yet, too often, fear of failure keeps people from taking the very risks that could lead to breakthroughs.

Beware the ego – the enemy of learning

You might think that those who’ve achieved more success would be more willing to risk failure—but that’s often not the case. The higher people climb, the further they have to fall, and that can make them more risk-averse, not less. At the same time, many become less willing to acknowledge their role in setbacks within their organizations.

Sydney Finkelstein’s research at Dartmouth’s Tuck School of Business found that as executives rise through the ranks, they often take less responsibility for failures. In his book Why Smart Executives Fail, he highlights how some of the most talented leaders fall into the trap of deflecting blame, rationalizing poor decisions, or surrounding themselves with people who won’t challenge them. The result? They miss out on the very lessons that could make them better, more effective leaders. And when leaders fail to learn, their organizations stagnate.

So let me ask you:

• What’s the most valuable lesson your failures have taught you?
• Where is your fear of failing keeping you from taking the very actions that would accelerate your learning toward more success?

If there’s one thing I’ve learned from studying how we can develop courage—a learnable skill—it’s that courage without the humility to learn as we go can leave us living in circles, repeating the same mistakes. There is a distinct difference between twenty of living and living the same year twenty times. Without the ability to reflect on and grow from failures, we limit our own potential—and in turn, the potential of those we lead.

The reality is that we are all going to fail; either we will fail to try, or we will try and fail to get the outcome we want. Either way, failing to learn from failure is failing twice. As Richard Branson puts it: “Do not be embarrassed by your failures, learn from them and start again.”

Dr. Margie Warrell is a sought-after speaker on leading with courage, an executive coach and author. Her latest book, The Courage Gap helps people take smarter risks, fail better and lead stronger outcomes.