To Be Lost is Simply to Be Becoming

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.