The secret to moving through uncertainty
On Saturday morning, International Women’s Day, I had the honor of speaking at Esq. Apprentice, a nonprofit that supports women of color on their journey to becoming lawyers.
The topic was “Trusting Yourself: Navigating Fear & Resistance.” I shared a Cherokee fable you may know.
A long time ago, a grandfather sat with his grandson and told him:
“There is a battle inside all of us, between two wolves. One wolf is fear and worry. The other is wisdom and love."
The grandson, wide-eyed, asked, “Which wolf wins?” The grandfather smiled.
“The one you feed.”
I love this story because it reminds me that we always have a choice in where we put our energy. And yet, how often do we unknowingly feed the wolf of fear—focusing on doubt instead of hope?
Fear is persuasive, and the toughest part is that it sounds rational.
It tells you that the chances of getting that job or promotion are zero. That your boss won’t agree to you moving to another department. That you have to be more “realistic.”
I know this voice well.
Some mornings, I wake up feeling fully empowered, like I am exactly where I need to be. Other times, my mind is in the grip of fear, questioning whether I’m doing enough, whether I’m doing it the right way, or where the world is headed in these uncertain times.
And after coaching hundreds of leaders, I know I’m not alone in this.
We all have moments—or even days—of doubt. We all have inner voices shaped by fear. And yet, our hearts always ask us to move forward anyway.
The Growth Cycle: Why Fear Feels Like Failure
Every time we step into something new—a career change, new leadership role, or creative project—we move through a natural cycle:
Inception (Vision) – That first spark of inspiration, the feeling that something big is possible.
Doubt & Resistance (Uncertainty) – This is where fear-based Saboteurs show up, whispering all the reasons we should stop. “Abort now!”
Experimentation (Messy Middle) – This is where courage is born. You take steps even when you don’t feel ready. You learn. You adjust. The fear doesn’t go away, but it stops making your decisions for you.
Breakthrough (Flow & Clarity) – Your confidence stabilizes. The fear is still there, but it now feels like part of the process.
But most of us mistake Step 2—Uncertainty—as failure.
In his book "Immunity to Change," Dr. Robert Kegan, a developmental psychologist at Harvard, explains that people resist change even when they consciously want it. He describes how, when we transition from old ways of thinking into new ones, we experience a disorienting phase before clarity emerges.
So if you feel uncertain, you’re not stuck—you’re on the verge of something new.
"Every outcome or circumstance can be turned into a gift and opportunity if you choose to see it that way." — Shirzad Chamine
You don’t have to give up when you’re in Uncertainty or Messy Middle stage, or wait until fear disappears (because it doesn’t).
You just have to stop letting it drive. That’s where Breakthroughs happen.
