Iconoclastic Leadership: Embracing Reality’s Shifts

“All reality is iconoclastic.” – C.S. Lewis

Every so often, something in our lives strikes us with that unmistakable jolt, such as a word, an event, a conversation, that makes us pause and say, “Hmm,” or even “Oh.” The question is: do we move on, or do we stop long enough to ponder, and let it teach us something?

Recently, a single word did that for me: iconoclasticcharacterized by attack on cherished beliefs or institutions. I heard it on a podcast, and it lodged itself so deeply that it followed me into my dreams. As I sat with it, I realized how many moments in my life have felt like a shattering of expectations. And, I have seen that more deeply it is a shattering of assumptions and beliefs I didn’t even know I was holding. That kind of shattering is uncomfortable, but it’s also a doorway. It invites us into grief, reflection, and ultimately, transformation. We move to something new.

For leaders navigating a world in upheaval, embracing the iconoclastic isn’t optional. It’s essential.

Why Leaders Must Pay Attention to the Iconoclastic

When our assumptions no longer match reality, our decisions drift off course. It is like navigating with a compass that’s a few degrees off true north. Each step seems small, but over time, the distance from where we intended to go becomes significant.

The iconoclastic moments are signals. They tell us that something needs updating. They may feel inconvenient, emotional, or time-consuming, but ignoring them only compounds the misalignment.

A new book by Marshall Goldsmith and Cornelia Choe, The Panoramic Leader, captures this beautifully: your decisions are only as good as the world you can see. Their premise echoed what this word had already stirred in me. Leaders must widen their perspective, especially when reality challenges their long-held beliefs.

What Holds Us Back: Fear and Ego

Two forces often keep leaders from engaging with the iconoclastic:

  • Fear – The unknown is unsettling. Leaders often feel pressure to “be the ones who know,” and iconoclastic moments expose the truth that we don’t always know. That can feel like losing control.
  • Ego – To admit we don’t know is an act of humility. It can shake our identity as leaders. Yet, on the other side of that humility is freedom. This is the freedom to learn, adapt, and lead with authenticity that helps our leadership expand.

Both fear and ego are natural. But they are also invitations to grow. What do you see as holding you back?

How to Embrace the Iconoclastic

Slow down. Adaptive leadership calls this the “balcony view”. It is stepping back to see the broader landscape rather than reacting from a short-sighted perspective.

Seek perspective. Who else has insight into the challenge you’re facing? What might they see that you don’t?

Notice what’s already breaking. Has something stopped working? Are you pushing forward with a plan that no longer fits reality? The cracks may be pointing toward innovation.

Return to your values. They are your internal compass. When reality shifts, values help you discern the next right step.

Allow yourself to grieve. When assumptions shatter, there is loss. Naming that loss creates space for something new to emerge.

Moving Through to the Other Side

Lewis said all reality is iconoclastic. Another favorite quote for me is by Richard Rohr, which he phrases as a prayer: “Lord, humble me in the presence of my reality.” Together, these ideas remind us that leadership isn’t about clinging to what was nor to an outcome. It is about courageously facing what is.

Iconoclastic moments may feel negative at first glance, but they hold beauty. They clear away what no longer serves us and make room for clarity, innovation, and deeper authenticity.

So, what is iconoclastic for you right now professionally or personally? And what is one step you will take as you move through it?

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