24. Coaching: courage enabler
Coaching and courage
Yesterday, I spoke with a coach friend about what executive coaching really is. “There’s so much confusion,” she said. People often think coaching is about giving advice, fixing problems, or teaching leadership skills. Others confuse it with therapy.
My current definition is simpler: coaching is courage enabling. Coaching, at its core, helps people access and exercise the courage they need to make meaningful changes in their lives.
What courage really means
I remember when I left my supply chain leadership role at a renewable energy company to become a self‑employed executive coach. On paper, it made no sense — completely different skills, no prior experience working for myself, and no clear roadmap. But it started with recognizing the pain I was experiencing in my own leadership. That pain led me to enroll in a coaching training program. The work of coaching felt deeply connected to who I was, yet I still couldn’t fully make the leap. It wasn’t until I began working with an executive coach that my passion for change became clearer. Through that process, I found the courage to define small, deliberate steps toward a different life — and, more importantly, to take them.
What is courage? Philosophers have wrestled with courage for centuries. Aristotle described it as the “golden mean” between recklessness and cowardice — knowing what to fear, what not to fear, and acting wisely. Paul Tillich, in The Courage to Be, framed it as affirming your existence even when anxiety and doubt threaten to overwhelm you. Existentialists like Camus and Sartre saw courage as showing up authentically — refusing to live someone else’s script when the world offers no guarantees.
In my work, I see three kinds of courage again and again:
Courage to see reality clearly — facing what is, even when it’s uncomfortable.
Courage to take the first step — moving out of the familiar and into possibility.
Courage to persist — continuing when resistance, setbacks, or pushback arise.
In leadership and self-authoring, courage is often quieter than we imagine. It isn’t always about grand gestures. Sometimes it’s saying no to a meeting invitation from an influential figure, taking three weeks away to rest and reflect, or initiating a difficult conversation. These small, deliberate acts slowly shape who we become.
The open door, Peter Vilhelm Ilsted
Why courage feels fard
Most coaching clients I meet live with an internal tension between what they think they “should” do and what they actually do each day. Often, this tension plays out through the three types of courage:
Some don’t yet have the courage to see clearly. They sense a deep unease, a knot in the stomach, but can’t name what’s wrong. Without unpacking that, they stay stuck. Others struggle with the courage to take the first step. They know something needs to change but surrender to thoughts like, “It’s just the way it is,” or, “I don’t know what I can do.” Feeling trapped, they imagine no options at all. Then there are those who fear carrying through. They hesitate because of potential fallout such as being judged, reprimanded, sidelined, or losing financial security.
Most people believe this third barrier is the biggest deterrent. But after deeper conversations, many of my clients realize that the first two deserve far more attention. You can’t persist with courage if you don’t yet see clearly or believe you have agency.
Cultural values often make these struggles more complex, especially for Asian Americans. Many of my clients grew up with messages shaped by filial piety, group harmony, and saving face. For them, courage can feel like betrayal of parents’ sacrifices, community belonging, or deeply held norms about respect. I often hear quiet resignation: “Life is suffering. That’s just how it is.”
Others swing the opposite way. After years of silence, their frustration builds until they fantasize about rebellion: “I want to scream at my boss and quit.” For them, courage feels possible only through burning everything down.
Coaching as a courage enabler
One client came into coaching deeply frustrated by the lack of growth in her role. Her boss rarely gave feedback, didn’t recognize her contributions, and offered little support. She felt unseen and stuck. Through coaching, we slowed down to unpack her story — what she expected, where her voice had been silent, and what truly mattered to her. Together, we brainstormed small experiments: sharing her work more visibly, initiating conversations with peers, inviting feedback differently.
Three months later, something shifted. After leading two highly visible projects, her boss began to recognize her contributions and provide resources she had long requested. In coaching, we explored what this meant: Should she pause her job search? Should she test whether this recognition signaled deeper, long-term change?
Coaching didn’t “fix” her situation. It gave her clarity, helped her design and test new actions, and provided accountability. Most importantly, it helped her step out of frustration and into agency.
An invitation
What would it be like if someone asked you: What’s the most important change you want to make right now?
What if you had a partner to brainstorm small experiments, hold you accountable, and help you navigate the pushback you might face along the way?
This is why I think of coaching as courage enabling. It creates the conditions for seeing more clearly, experimenting with possibility, and staying grounded when fear arises.
The courage itself has to come from you — but you don’t have to walk the path alone.