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 ... Show More
Today
Me, But Better: Olga Khazan On The Science of Personality Change, Challenging Fixed Mindsets, & The Big Five Traits That Shape Your Life
Olga Khazan is a staff writer for The Atlantic and author of "Me, But Better." This conversation explores personality mutability and Olga's experiment to transform from anxious introvert to someone freed from her own patterns. We discuss the Big Five traits, her Miami breakdown t ... Show More
2h 12m
Aug 18
Addiction, Celebrity, Public Shaming & Truth: The Performance Art of James Frey, Celebrated Writer of Ill-Repute
James Frey is the author of "A Million Little Pieces," a book that spoke to the deepest, darkest parts of countless readers in early recovery. This conversation explores his journey to become literature's bad boy, his heroes like Baudelaire and Henry Miller, and his philosophy of ... Show More
2h 34m
Aug 14
ROLL ON: The State of Podcasting In 2025
Roll On resurfaces from the chrysalis! Adam Skolnick and I unpack 90 days post-surgery, why the caterpillar needs a tortoise mind to become a butterfly, and the death of authentic podcasting. On tap: The state of Podcastistan, why I'm breaking up with viral culture, and the unexp ... Show More
1h 35m
Feb 2024
Chip Conley: How to Thrive in Midlife
Do you want to make your midlife the best years of your life? Joining Sarah Grynberg this week is hospitality visionary and bestselling author, Chip Conley. Chip is the founder of Joie de Vivre Hospitality, and Modern Elder Academy, and the former Head of Global Hospitality and S ... Show More
1 h
Apr 2024
Chip Conley on Learning to Love Midlife
Chip Conley is a bestselling author and co-founder of the Modern Elder Academy, the world’s first “midlife wisdom school”. After an impressive career in the hospitality industry, first as the founder of Joie de Vivre Hospitality, then as Airbnb’s Head of Global Hospitality and St ... Show More
42m 52s
Jan 2024
Making Peace with Your Midlife, Mid-career Self
Research shows that happiness bottoms out for people in their mid to late 40s. We might struggle with mid-career slumps, caring for both children and aging parents, and existential questions about whether everything has turned out as we'd planned. But Chip Conley says we can appr ... Show More
29m 27s
May 2023
What’s It All For? Loss and Meaning In Midlife with Chip Conley
Midlife has a lot of messy stuff in it: divorce, the death of your parents, menopause, health scares, empty nests, career changes, feeling increasingly irrelevant - “midlife” has terrible branding, according to author, modern elder, hospitality expert, and CEO and co-founder of M ... Show More
47m 30s