In this episode, Margaret and David explore what it means to smile at fear — and how this practice can help us become braver, more self-aware leaders. Drawing on David’s book, The Spiritual Path of Leadership: Awakening Your Inner Sage, they explore how fear shapes our behavior, why we sometimes withhold what needs to be said, and what becomes possible when we choose courage over avoidance.
Smile at Fear: What’s Really Holding Us Back?
As leaders, we often need to have difficult conversations. We need to give feedback, name problems, or share an idea that might challenge the status quo. But before we ever open our mouths, our minds can become a movie theater of worst-case scenarios. What if someone gets angry? What if we hurt their feelings? What if they quit?
These fears often have roots in earlier experiences of being shamed, criticized, or punished for speaking up. David shares a banger of an example, a time he tried to solve a problem on the board in math class, got the wrong answer, and had the teacher throw an eraser at his head and tell him to sit down.
We learn to protect ourselves by staying quiet, avoiding conflict, or retreating into a comfortable cocoon. For example, David decided that he was forever finished with getting up in front of the class.
David and Margaret invite listeners to recognize these patterns with compassion rather than judgment. Fear may have served us in the past, but it doesn’t have to make our decisions for us today.
The Price of Staying Silent
Speaking up has risks and often comes with a price tag. But so does silence.
When we withhold what we think, feel, or know, when we don’t name what IS, we must deal with a different price tag.
When leaders avoid difficult conversations, teams lose opportunities to surface important information, solve problems, and make better decisions. Team members lose opportunities to grow. Silence can also create awkwardness, erode psychological safety, and fuel the familiar “meeting after the meeting,” where people say what they didn’t or couldn’t say in the room. This fuels triangulation and cultures of gossip.
The goal isn’t to speak without considering the impact of our words. It’s to recognize that avoiding discomfort isn’t always the kindest or most constructive choice.
Make Room for Courage, Compassion, and Intuition
So what does it mean to smile at fear? First, notice it. Instead of treating fear as a stop sign, greet it like an old friend: Oh, there’s that guy again. Then, consider both scenarios: what might happen if you speak up and what might happen if you don’t.
Courage doesn’t require us to become comfortable with discomfort–or with fear. Rather, smiling at fear invites leaders to allow the discomfort to be there … and choose our next action anyway. Self-compassion can help: acknowledge that you’re experiencing a difficult moment, remember that you’re not alone, and offer yourself some kindness as you take the risk.
Margaret shares a personal example of finally having a conversation with her partner. She had written an essay about something she does, but was reluctant to publish it because it named some things about her partner that she’d been hesitant to say out loud. After sitting in fear for weeks, she finally smiled at the fear and shared it with him. By speaking honestly and taking accountability for her own behavior, she helped bring an unspoken issue into the open. What she’d feared might be painful instead created relief and validation for him. (Here’s the essay on Substack)
What Happens After You Speak?
Speaking up is only part of the practice. Once you’ve said the thing, stay present. Notice how it lands. Listen, take responsibility for your impact, and be willing to learn or repair if needed. You can’t control another person’s reaction, but you can choose how you respond.
The invitation is simple: the next time fear tells you to stay silent, try smiling at it. You might discover a different path forward.
