The Wise Owls in the Leadership Tree: Cultivating Your Kensho Flock

Leadership is not a solitary endeavor. It thrives in connection, nurtured by the wisdom of those who guide, challenge, and inspire us. In my leadership journey, I’ve come to call these mentors my “Wise Owls”—figures perched high in the canopy of my leadership tree, offering perspective, insight, and encouragement to help me grow.

The metaphor of the tree is central to how I view leadership. Like a tree, a leader is rooted in core values, strengthened through resilience, and stretched outward by the branches of connection and influence. The fruit of this growth is the wisdom we share and the impact we leave on others. However, no tree grows in isolation; it is nourished by the ecosystem surrounding it. For leaders, this ecosystem is our Kensho Flock—a circle of Wise Owls whose guidance helps us to thrive.

Racing across open waters has taught me profound lessons about leadership, mirroring the unpredictable storms leaders face. Just like a tree weathering wind and rain, leadership requires deep roots, flexible branches, and the resilience to stand tall through adversity.

The Resilient Leader: Rooted in Purpose, Flexible in Action

The wisdom of the tree offers a timeless metaphor for leadership. A resilient tree doesn’t resist storms; it bends, absorbs, and adapts while remaining deeply rooted in the soil that sustains it. Leaders who embody this wisdom recognize that strength comes from within—anchored in values, nourished by learning, and tested by challenges.

What if the secret to authentic leadership lies in something as simple as a tree? Trees embody resilience, adaptability, and connection, offering profound lessons for leaders. Like a seed growing into a strong and flexible tree, leadership requires nurturing roots in self-awareness, values, and relationships, while branches extend outward toward growth and opportunity.

The tree’s wisdom isn’t about striving for perfection but embracing change, balancing strength with vulnerability, and fostering collective growth. From the “wood wide web” of interconnected roots to the ability to bend without breaking in a storm, trees remind us that true leadership thrives through connection and adaptability.

“I fear being judged.” This powerful sentiment has gripped my heart, often stifling my voice and clouding my actions with doubt. The fear of judgment can quietly infiltrate our lives, influencing decisions and self-perception. Through my journey, I found inspiration in Jamie Kern Lima's "Worthy," which illuminated the path to embracing vulnerability. Lima's story transformed my perspective, turning fear into an opportunity for growth. Let’s explore this together, cultivating self-compassion and courage, and reclaiming our power to define our worth amidst the noise of judgment.