Reboot Podcast Episode #171 – The Great Midlife Edit – with Chip Conley

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.


Chip Conley

Chip Conley

Modern Elder Academy (MEA) founder and New York Times bestselling author.

View Bio

Episode Description

In this episode of The Reboot Podcast, Jerry Colonna sits down with the insightful Chip Conley, author of Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age. Together, they explore the transformational journey of embracing midlife as a time of growth and wisdom. Chip shares his personal tale of crisis and renewal, emphasizing the fear and cultural pressures surrounding aging.

They ponder the role of an elder and the importance of embracing uncertainty, impermanence, and transition in life. The conversation touches on the significance of emotional intelligence, the three stages of transition, and leaving a positive legacy for future generations.

Helpful links: 

Join Jerry and Chip at M|E|A this September for their workshop, “Reboot: Leadership & the Art of Growing Up.” This program is for leaders (you don’t have to be a start-up CEO) who want to deepen their relationship with themselves and others so they can make a bigger impact in the world. Register here. 

Learning to Love Midlife | Wisdom at Work: The Making of a Modern Elder | Men at Forty by Donald Justice | The Midlife Unraveling by Brene Brown | How We Live Is How We Die | How Will You Measure Your Life | The Guest House by Rumi | The Anatomy of a Transition

Podcast Topics