Courageous Leadership: Why Playing It Safe Is the Biggest Risk

Oct 19

The most expensive career decision I ever made was selling myself short and calling it sensible.

At the time, it sounded responsible. I could explain my choices in ways that made other people comfortable. What I had a harder time admitting was how often I let the fear of disappointing someone, looking inexperienced, or getting it wrong decide what I would allow myself to want.

I have been scared to walk into rooms I worked so hard to reach. Scared to travel abroad after becoming a mother. Scared to leave a role that looked impressive on paper. And scared to tell people I was starting over. Again.

So when I talk about courageous leadership, I am drawing on moments when I wanted to retreat and had to ask myself why. Was I protecting something that mattered, or avoiding the discomfort of being seen trying?

That question has followed me from elevator sales to the United Nations, through motherhood and into building businesses of my own. The answer has rarely arrived neatly. But each chapter has helped me understand what it means to trust myself a little more.

Learning to Belong Before I Felt Ready

When I accepted a role with the United Nations Children’s Fund at 32, I had never even been to New York. Suddenly, this woman from Kansas City, who had been selling elevators and escalators, was stepping into a world of global diplomacy and humanitarian work.

I had a new baby, a relatively new marriage, and a dream I had carried for years. I also had absolutely no idea how to feel at home in the rooms I was about to enter.

On my first day, people asked whether I lived on a farm in Kansas or rode a horse to visit my neighbors. I smiled, but those questions made the distance between where I came from and where I was standing feel a little bit bigger.

Fortunately, I had a plan. At least for my outfit.

I had gone to Macy’s and bought a beautiful white coat, sleek black pants, and a pair of heels. I pulled my hair into a tight bun and dressed like a woman who knew exactly what she was doing. Getting dressed was one part of the day I could figure out, even when navigating the room felt considerably less straightforward.

I wanted to do meaningful work. I also wanted people to believe I deserved to be there. Both were true, and I can admit now that the second desire sometimes got in the way of the first.

There were times I overcompensated for my uncertainty by creating rigid boundaries with my team. I was still learning that being taken seriously did not require me to hold people at a distance or to have the answer to every question. In those moments, the fear of vulnerability far outweighed my own confidence. Other times, I helped build partnerships that made a real difference for children in some of the world’s most marginalized communities. Those moments reminded me why I had wanted the work so badly in the first place.

I still remember giving a presentation in a room filled with heads of state, private-sector partners, and global diplomats. I stammered my way through it, painfully aware of every uneven sentence. When I finished, my boss smiled, nodded, and quietly said, “You got through it.”

She had let me find my way through a difficult moment without taking over or making me feel small. Her response gave me something I needed more than a perfect performance: evidence that I could be uncomfortable and still contribute. She taught me what capability truly meant. To be capable simply requires you to be courageous.

That is how confidence began to grow for me. I did something difficult, survived the imperfect parts, and had a little more experience to draw on for the next time around.

Looking back, I wish I could tell that woman in the white coat that she did not have to edit Kansas out of her story. She could bring her own experiences into the room and learn from the people already there. Belonging did not require becoming someone else.

It is a lesson I return to when I work with leaders today. How much of your energy goes toward proving you belong? And what might become possible if you could put some of that energy into the contribution you came to make?

Finding My Way as a Mother and a Leader

Learning to trust myself at work was one kind of courage. Learning to trust myself as a new mother asked something different of me.

After my firstborn arrived, traveling abroad for work felt different. The thought of going to war-torn countries carried a weight it had not carried before. There was a little person at home who depended on me, and I took that responsibility seriously. I loved the work, but I was scared to leave her.

My husband, Jeff, reminded me that I needed to return to what made me me.

I needed to hear that from someone who understood how much I loved our family. He could see that the part of me drawn to the world, to people, and to meaningful work was still there. Becoming a mother had changed my life profoundly, and I was trying to understand how all of those parts of me could live together.

The answer required care, preparation, and honest conversations about what our family needed. It also required me to acknowledge that having a mission beyond home did not diminish the love I felt inside it.

That experience changed the questions I asked myself. Alongside “What am I afraid of?” I began asking, “What matters enough to work through this fear?”

So, my questions to you are simple. What lights you up? What is your mission? Which parts of yourself have you quietly set aside because you cannot quite see how they fit into the life you have now?

For me, family, purpose, and connection all mattered. Understanding that gave me a foundation for making decisions. I could consider an opportunity in light of my values, rather than letting either fear or excitement make the decision for me.

Courage in leadership needs that same foundation. Otherwise, we can spend years proving we are brave enough to pursue a life we do not actually want.

Being Honest When a Chapter No Longer Fits

Understanding my values helped me recognize another uncomfortable truth: sometimes I was drawn to an opportunity because I liked how it sounded when I told people about it.

I have loved work that was neither glamorous nor easy to explain. Building my residential construction business, for example, has brought me joy I did not always know how to talk about alongside international affairs or keynote speaking. I was quicker to share the parts of my career I thought would impress people.

It took time to recognize how much influence that instinct could have over my choices. And it made the lesson I learned at St. Jude particularly personal.

I loved the people I worked with and deeply respected the mission. I still do. Yet I came to understand that the role did not align with the scope of leadership and direction I wanted to pursue.

Admitting that was hard because I had chosen it. I questioned my judgment. I wondered whether I should give it more time. I reminded myself how fortunate I was to have the opportunity at all.

Underneath those thoughts was a question I found harder to say out loud: What would people think if I left?

I had to separate my gratitude for the organization from my responsibility for my own future. I could appreciate the opportunity and the people while recognizing that I wanted to build something different.

Leaving meant giving up the reassurance of a recognizable institution. I would have to explain what I wanted in my own words, then take responsibility for pursuing it. I did not have every answer, but I was becoming clearer about the cost of continuing to ignore what I knew.

An organization can do extraordinary work and still be the wrong fit for your next chapter. Recognizing that calls for honesty, respect, and a thoughtful transition. It also calls for a little compassion toward the person who made the original decision with the information she had at the time.

I am still learning that last part.

Letting People See Me Begin Again

Each of these experiences has made the next chapter possible, even when the connection was hard to see at the time.

I have sold elevators, served as a Vice President at UNICEF USA, worked at St. Jude, built a speaking practice, and started a residential construction business. Put those chapters together and I might sound like someone who finds change easy.

Living them has felt considerably less tidy.

With every new beginning, I have wondered whether people would understand. Would they think I had lost my direction? Would I have to explain myself if it did not work?

Yet once I said what I wanted out loud and began doing the work, those imagined reactions took up less space. There were decisions to make, people to serve, and problems to solve. My attention had somewhere more useful to go.

I can see now that I brought something forward from each experience. The woman who sold elevators is still here. So is the woman who walked into the United Nations feeling intimidated, and the mother who was afraid to get on a plane. I draw on all of them in the work I do today.

For me, the courage of leadership includes allowing people to see that evolution while it is still happening. We ask others to learn, adapt, and try again. There is value in letting them see us do it, too.

Making Courage Part of Everyday Leadership

Of course, most opportunities to practice courage arrive in the middle of an ordinary day. You may need to voice a concern in a meeting, admit that an approach you championed needs to change, or apply for the responsibility you keep hoping someone will offer you.

The decisions look different, but I have found a few practices useful across all of them.

1) Start With What Matters to You

Before asking whether you are brave enough to pursue something, ask why you want it. A promotion might offer financial stability, greater contribution, or the chance to shape a team. Understanding what you hope to gain helps you decide what the opportunity is worth.

One question I find especially revealing is this: If no one were impressed by this decision, would I still want to make it?

2) Get Specific About the Fear

Once you understand what you want, name what is holding you back. Finish the sentence, “If I do this, I am afraid that…” and be as honest as you can.

Losing income calls for a different response from looking inexperienced. One may require a financial plan; the other may require accepting that learning is visible. Specific fears give you something to prepare for, question, or discuss with someone you trust.

3) Give Staying the Same Equal Attention

We are often thorough about what could go wrong if we change. Consider the consequences of continuing as you are with the same care.

If nothing changes for another year, what happens to your energy and contribution? What happens to your team if the difficult conversation never takes place? A familiar choice still has consequences. Include them in your decision.

4) Take a Step That Helps You Learn

You do not need to solve the entire future before making your next move. Request the conversation, put numbers around the business idea, or offer your perspective in the meeting.

Choose an action that gives you useful information. You may discover that you need more preparation, or that the opportunity is closer than you thought. Either way, you have something more concrete to work with than anticipation.

5) Invite an Honest Perspective

Jeff’s reminder mattered because he knew the person underneath the fear. Find someone who understands your values and can help you think clearly about your choices.

You still own the decision. But someone who knows you well may notice when the explanation you have rehearsed so carefully no longer sounds like you.

Choosing a Life I Believe In

These practices have not made every decision easy, and I cannot promise that every courageous choice will work out the way you hope. Some of mine have involved disappointment, awkward explanations, and a very real wish that I had known more before I began.

I also know what it feels like to make myself smaller so my life is easier to explain. I have spent enough time doing that to recognize the cost.

So when I catch myself hesitating now, I try to slow down and listen. Is there a responsibility I need to honor? A practical problem I need to solve? Or am I giving someone else’s imagined opinion more authority than my own values?

I think about the woman in the white coat. I feel a tenderness toward her now that I struggled to offer myself then. She was trying so hard to get everything right. She could not yet see how much she would learn by showing up as she was.

Perhaps there is a version of you who needs that same kindness today. The one considering a new role, preparing for an honest conversation, or quietly admitting that she wants something different.

You can be grateful for the life you have built and still be curious about what comes next. Begin with one honest admission, then one thoughtful step. Let yourself learn along the way.

One day, someone you love may come to you afraid to pursue something that matters deeply to them. I hope you can tell them about a time you were afraid, too, and how you found your way forward.