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Christopher Kolenda - Leadership Development Expert & Strategic Advisor; Retired Army Colonel; Bestselling Author of "Zero Sum Victory: What We're Getting Wrong About War"

Christopher Kolenda

Profile updated October 11, 2025
LocationTravels from Milwaukee, WI, USA
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$10,000 - $20,000
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About Christopher Kolenda

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Why Not? How 1,700 Miles on a Bike Revealed the Secrets to Achieving Improbable Goals

What would you dare to do if you knew you would succeed?

By answering that question, you’ve identified a transformation zone goal.

But here’s the challenge: you cannot achieve transformation zone goals using comfort zone habits.

Discomfort lies between comfort and transformation; it’s the zone where you fear everyone will watch you fall on your face. That fear prevents you from moving forward on goals that light you up.

What if you had a proven, repeatable way to navigate discomfort safely?

This keynote is for CEOs and high-performing leaders who want to break through barriers to growth and ignite their transformational goals.

Told through the lens of a 1700-mile bicycle ride to honor his unit’s fallen soldiers, Chris Kolenda illustrates how you cross the bridge between current performance and future potential.

Mastering this process enables you to:

  • Envision your transformation zone goals
  • Develop the strategies you need to break through your comfort zone and turn discomfort into growth
  • Activate the resilience to bounce forward relentlessly from challenges
  • Ignite new possibilities previously hidden from view.

With compelling stories and actionable strategies, Kalenda equips you with practical steps for navigating the discomfort zone, so you grow beyond your perceived limits and build the endurance to reach extraordinary heights.

You’ll describe your transformation zone goal and have the confidence to write Why Not in front of it.

Actionable Objectives you will gain strategies to:

  • Inspire people to contribute their best to your organization’s success.
  • Master ways to respond to challenges and avoid self-sabotaging reactions.
  • Determine who to put in your inner circle and who to keep away from it.
  • Create 1mm adjustments that deliver massive impact.
  • Recognize and address emotional triggers undermining your credibility.
  • Build bridges that inspire co-creation, and avoid walls that invite friction.

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Books by Christopher Kolenda

Transforming How We Fight - Book by Christopher Kolenda

Transforming How We Fight” (2025)

Transforming How We Fight

Zero-sum Victory What We're Getting Wrong about War - Book by Christopher Kolenda

Zero-sum Victory What We're Getting Wrong about War” (2021)

Zero-sum Victory What We're Getting Wrong about War

Leadership The Warrior's Art - Book by Christopher Kolenda

Leadership The Warrior's Art” (2021)

Leadership The Warrior's Art

The Counterinsurgency Challenge A Parable of Leadership and Decision Making in Modern Conflict - Book by Christopher Kolenda

The Counterinsurgency Challenge A Parable of Leadership and Decision Making in Modern Conflict” (2012)

The Counterinsurgency Challenge A Parable of Leadership and Decision Making in Modern Conflict

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