• Fireside Chat

Modern Leadership: The Courage to Lead Differently

Jerry Colonna & Chip Conley

Gather with REBOOT author and legendary CEO coach Jerry Colonna, alongside MEA founder and renowned entrepreneur Chip Conley, for a powerful live session examining the next frontier of leadership—radical self-inquiry. Discover why successful leaders are embracing vulnerability and conscious growth as pathways to creating meaningful impact in the world.

What You’ll Learn

  • The unexpected ways vulnerability and authenticity amplify your leadership influence
  • The reasons why better leadership begins with transforming your relationship with power
  • How to turn professional achievement into meaningful impact through radical self-inquiry
  • How to access deeper wisdom that transforms both you and those you lead

Can’t join us live? No problem! Register now and get the full replay sent straight to your inbox.


February 10, 2025 11:00 AM PT 02:00 PM ET

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Meet Your Hosts

Jerry Colonna

Author of “Reboot: Leadership and the Art of Growing Up” and “Reunion: Leadership and the Longing to

Jerry Colonna is the CEO and co-founder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. Prior to his career as a coach, he was a partner with JPMorgan Partners (JPMP), the private equity arm of JP Morgan Chase and he co-founded Flatiron Partners.

Chip Conley

Chip Conley is a hospitality entrepreneur, author, and the founder of MEA.

Chip is a three-time TED speaker and the New York Times bestselling author of Wisdom at Work: The Making of a Modern Elder and Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age. As founder of the second largest boutique hotel chain in America and “modern elder” to the young Airbnb founders, Chip is a globally-recognized thought leader on the future of work and the competitive advantages of a multi-generational workplace.

Inspired by his experience of intergenerational mentoring at Airbnb – where his guidance was instrumental to the company’s extraordinary success – Chip founded MEA in 2017 to help other people in midlife find their own meaningful way to keep learning and sharing the wisdom gained from their lived experiences to create fulfilling and exciting second adulthoods. Since then he has dedicated much of his life to reframing the concept of aging and helping people navigate midlife with renewed purpose and possibility.

Discover Upcoming Wisdom

Who Am I Now? Clarity and Freedom to Thrive

Jill Nykoliation & Derek Gehl
May 1, 2025 1:30 PM PT 04:30 PM ET

After decades of moving at a million miles an hour – striving, building, compromising, accomplishing – have you paused to reflect on who you truly are now?

Join host Derek Gehl for an illuminating conversation with human insight specialist and award-winning business leader and brand strategist Jill Nykoliation. From guiding global brands to coaching executives through pivotal life transitions, Jill brings a unique perspective on identity and reinvention.

Just a few things we’ll explore:

  • The Science of Identity – what research tells us about shedding outdated versions of ourselves
  • The Midlife Opportunity – why this stage offers unique potential for transformation
  • The Liberation of Clarity – how defining who you are now creates freedom to thrive

Whether you’re feeling stuck in old patterns, seeking greater purpose, or simply curious about the next chapter of your life – you’ll leave this live chat with practical insights and renewed excitement about who you’re becoming.

Crossroads & Classics: Navigating Transitions with Art & Literature

David Carl, Dr. Claudia Hauer, Mary Hofstedt & Kari Cardinale
May 6, 2025 1:00 PM PT 04:00 PM ET

Join host Kari Cardinale for a warm and enlightening conversation with St. John’s faculty David Carl and Claudia Hauer, alongside MEA facilitator Lead Mary Hofstedt. Together, they’ll explore how classics, art, and poetry light our path through life’s transitions in this special MEA and St. John’s College collaboration.

  • The Power of Literary Wisdom – How Victor Frankl’s insights on choosing our response creates space for personal growth
  • Ancient Philosophy in Modern Life – Unpacking Plato’s allegory of the cave and the universal hero’s journey
  • Art as Transition Guide – Georgia O’Keeffe’s Santa Fe journey and how visual art illuminates our pathways

Come discover how the classics can walk beside you through life’s biggest moments in this special gathering of MEA and St. John’s College.