Jerry Colonna, often called the “CEO Whisperer,” is a former venture capitalist who helped shape the early development of Silicon Valley and went on to mentor many of its entrepreneurs. His book Reboot: Leadership and the Art of Growing Up (2019) challenges the myth that success is about control and certainty. Instead, he invites us to see leadership—and life itself—as a process of becoming, where doubt and disorientation aren’t failures but essential teachers:
What if being lost is part of the path? What if we are supposed to tack across the surface of the lake, sailing into the wind instead of wishing it was only at our backs? What if feeling lost, directionless, and uncertain of the progress is an indicator of growth? What if it means you’re exactly where you need to be, on the pathless path?
Being lost isn’t failure; it’s part of the journey itself. When we feel uncertain or directionless, it’s often a sign that we’re moving beyond the familiar, stretching into new territory. The discomfort of not knowing is less a mistake than a marker of growth.
The obstacle isn’t only something to overcome; it’s the guide that shapes us. Headwinds force us to adjust, to tack differently, to discover resilience we might never have found in calm waters. Ease comforts, but resistance transforms.
Idea for Impact: To be lost isn’t to lose—it’s to become.
You’re mid-presentation. Your palms sweat, your heart drums, and you’re convinced the room can see every sign of it. They can’t. Your internal state is private. The version of you the audience sees is far steadier than the one you feel.
Everyone carries an inner critic. It fills quiet moments with familiar doubts: I have to do this perfectly. If I try, I might fail. I’m not good enough. I’ll never catch up.
We romanticize transformation—new routines, cleaner diets, sharper habits. But in practice, change rarely arrives in cinematic sweeps. It comes in quieter forms: a switch from soda to water, a walk around the block, skipping the evening snack. Small choices. Easily overlooked. In aggregate, 
The biggest obstacles in your way aren’t out there; they’re in your head—and in your habits. Drop them, or they’ll drag you.
Are you finding it challenging to take action?
So, you’re asking, “How can I overcome my fear?”
Early in their careers, salespeople who make more calls often outperform their peers who make fewer.
Fear is a nuance of vulnerability. Being vulnerable often means