What if we framed midlife not as a crisis but as a transformative chrysalis—a liminal period where profound awakenings unfold?

What if we saw it as an opportunity to shed old layers, unfurl our wings, and share the pollen of our wisdom with the world?

Guiding us from pupa to butterfly, we have the Monarch himself, Chip Conley. 

Returning to the show for the second time (Chip first appeared on episode 681), Chip founded the Modern Elder Academy, the pioneering midlife wisdom school dedicated to transforming aging. He is also a New York Times bestselling author. In his latest book, Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age, Chip retools conventional notions of life in our 40s, 50s, and 60s. Drawing from the latest social science research, moving anecdotes, and enduring wisdom, he unveils 12 compelling reasons why life becomes more prosperous and fulfilling as we age.

Today’s conversation revolves around how we conceptualize and define life stages, the concept of Age Fluidity, the age curve of happiness, and the importance of cultivating regenerative communities. We also explore Chip’s personal journey with cancer, the distinction between showing up and showing off, the role of being a conduit for ideas and collaboration, the essence of being a Modern Elder, the concept of age apartheid, and the value of generational dinners.

For individuals seeking to infuse greater purpose and satisfaction into their professional journey, especially those who have dedicated a significant portion of their career to a specific path and are now pondering fresh opportunities, this conversation is a must-listen.

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Peace + Plants,

Rich