Courage Over Comfort: Why Vulnerability Makes Us Better Leaders

Written by Shanon Tysland | Founder, CEO at Experience Momentum

Years ago, I read Brené Brown’s Daring Greatly, and it changed the way I thought about courage.

The book begins with Theodore Roosevelt’s famous description of “the man in the arena”—the person who is willing to step forward, risk failure, and be seen trying. Roosevelt reminds us that the credit does not belong to the spectator offering criticism from a safe distance. It belongs to the person whose face is marked by dust and sweat, who falls short, gets back up, and continues to participate fully in life.

That image has stayed with me.

I want to be in the arena of life.

I do not want to stand on the sidelines protecting myself from embarrassment, discomfort, criticism, or failure. I want to participate. I want to build things, love people, raise a family, lead a team, serve my community, and keep redefining what is possible.

But entering the arena requires something from us.

It requires vulnerability.

Vulnerability Is Not Weakness

We often confuse vulnerability with weakness. We imagine it means being overly emotional, sharing everything with everyone, or walking through life without boundaries. That is not vulnerability.

Vulnerability is having the courage to be honest when the outcome is uncertain.

It is saying:

“I do not know.”

“I need help.”

“I got that wrong.”

“I am sorry.”

“I want your feedback.”

“This conversation is uncomfortable, but it matters.”

“I care enough about you to tell you the truth.”

Vulnerability is not the absence of strength. It is a deeper form of strength.

As Brené Brown has written, vulnerability is where creativity, innovation, and change begin. We cannot create something meaningful without risking that it may not work. We cannot build a trusting relationship without allowing ourselves to be known. We cannot become better leaders without acknowledging that there are things we still need to learn. To live fully is to be vulnerable.

Vulnerability at Home

I feel this most clearly as a parent.

Kelly and I are raising four children, ranging in age from five to fifteen. Parenting makes me feel vulnerable almost every day.

I want to be kind, patient, and emotionally available. I also want to establish boundaries, hold expectations, and prepare our children to navigate a world that will not always be easy.

Sometimes I worry I am being too kind and allowing myself to get railroaded. At other times, I worry I have been too firm and caused one of my kids to shut down.

There is no perfect formula.

Parenting continually exposes the distance between the parent I want to be and the imperfect human being I am. I lose patience. I misunderstand what one of my children needs. I react too quickly. I sometimes recognize afterward that I was trying to control a situation when I should have been curious about it.

Those moments can produce shame, or they can become opportunities for connection and growth.

I try to let my kids hear me say, “I’m sorry. I didn’t handle that the way I wanted to. I’m working to become better for you.”

Apologizing does not diminish my authority as their dad. I believe it strengthens our relationship. It shows them that love does not require perfection. It shows them that adults can take responsibility, repair relationships, and keep learning.

Perhaps one of the most important things our children can see is not a perfect parent, but a parent courageous enough to grow.

Vulnerability in Leadership

Business has exposed me in similar ways.

I am a physical therapist by training. I did not go to business school. Much of what I have learned about entrepreneurship and leadership has come through experience—the school of hard knocks.

I have made mistakes with people, finances, communication, strategy, and timing. I have waited too long to have difficult conversations. I have delivered feedback poorly. I have occasionally tried to protect people from discomfort when what they really needed was clarity.

Leading with both kindness and firmness is difficult. It is especially difficult when you care deeply about people.

At Experience Momentum, we talk about Radical Candor: the responsibility to care personally while challenging directly. It sounds straightforward, but practicing it requires courage. Candor without care can feel cruel. Care without candor can become avoidance. Human-centered leadership asks us to hold both.

It means telling someone the truth while protecting their dignity. It means addressing a performance problem without reducing a person to their performance. It means remembering that accountability and compassion are not opposites. In fact, honest feedback delivered with genuine care may be one of the most respectful things we can offer another person.

Avoiding the conversation might feel comfortable today, but it often creates more confusion, frustration, and resentment tomorrow. That is why vulnerability is foundational to two of our Operating Standards: Leadership That Develops People and Genuine Connection and Human Care.

We cannot develop people if we are unwilling to enter uncomfortable conversations with them. And we cannot create genuine connection if we are always performing certainty, strength, or perfection.

The Courage to Ask for Feedback

Several years ago, a team member gave me a handcrafted woodworking piece for my birthday. It contains three words made well known through Brené Brown’s work: Courage over comfort.

It sits in my home office, where I see it almost every day. Those three words have become a question I can return to: Am I choosing courage, or am I choosing comfort?

Comfort is assuming I am doing a good job. Courage is asking people how my leadership is affecting them.

Comfort is defending my intentions. Courage is listening to someone describe the impact of my actions.

Comfort is explaining why I made a decision. Courage is becoming curious about what I may have missed.

Comfort is waiting for feedback to arrive. Courage is actively inviting it.

Saying, “I want your feedback because I want to become better,” is an act of vulnerability. We are admitting that someone else may see something about us that we cannot yet see ourselves. That can be uncomfortable. It can also be transformational.

Some of the greatest breakthroughs I have experienced in leadership have occurred after I opened up about where I was struggling. When I stopped pretending I had the answer, people stepped forward with ideas, support, perspective, and truth.

Vulnerability does not eliminate leadership responsibility. It helps us carry that responsibility more honestly.

Strengthening the Vulnerability Muscle

I recently had a powerful conversation on the Redefine What’s Possible podcast with Reggie D. Ford, author, speaker, resilience expert, and creator of the Vulnerability Muscle Framework.

Reggie’s story includes childhood trauma, poverty, violence, achievement, healing, and the gradual realization that some of the behaviors that helped him survive were not the same behaviors that would help him thrive.

One of the most powerful ideas from our conversation was that vulnerability is a muscle. And muscles become stronger through use.

We strengthen vulnerability each time we tell the truth about what we are experiencing. We strengthen it when we walk into therapy, initiate a difficult conversation, admit a mistake, establish a boundary, or allow someone trustworthy to see beyond the polished exterior.

Reggie described vulnerability as trusting yourself enough to trust others.

That does not mean sharing everything with everyone. Discernment and boundaries matter. It means becoming secure enough in yourself that you can risk being honestly known by people who have earned that trust.

His framework also encourages leaders to model vulnerability, understand themselves, choose curiosity over criticism, listen to understand, and continually evaluate how they are growing.

These are not soft skills in the sense that they are easy or optional. They are essential human skills—and some of the hardest skills a leader will ever practice.

Choosing Curiosity Over Certainty

One practice that continues to help me is asking one more question. When someone disappoints us, disagrees with us, or behaves in a way we do not understand, our minds quickly create a story.

They do not care. They are lazy. They are disrespecting me. They should know better.

But what else could be true?

What pressure might they be carrying?

What expectation was unclear?

What am I contributing to this situation?

What have I not yet taken the time to understand?

Curiosity does not eliminate accountability. It helps ensure that our accountability is rooted in understanding rather than assumption. This is vulnerability, too. Curiosity asks us to loosen our grip on the belief that our first interpretation must be correct.

Staying in the Arena

Vulnerability will never be comfortable.

There will always be risk in asking for feedback, telling the truth, apologizing to a child, confronting a performance issue, sharing a struggle, or attempting something we may not do well. But comfort is not the goal. A fully lived life is the goal. Meaningful relationships are the goal. Better leadership is the goal. Growth is the goal.

The arena will leave us dusty. We will make mistakes. We will receive criticism—some of it valuable and some of it not. We will occasionally say the wrong thing, choose the wrong approach, or discover that we have more work to do.

The alternative is to remain safely outside the arena, protected but disconnected from the experiences that make us feel most alive.

I do not want that life. I want to keep choosing courage over comfort.

As a husband.

As a dad.

As a friend.

As a business owner.

As a leader.

And as an imperfect person who is still learning how to care deeply, speak honestly, listen openly, and become a little better each day.

The question is not whether we will feel vulnerable.

The question is whether we will allow that vulnerability to keep us on the sidelines—or whether we will choose to step into the arena anyway.