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 Modern Elder Academy Chip Conley.

What if midlife (and beyond) could include an ever deepening sense of self and more satisfying connections - right alongside all that cascading loss?

Chip and Megan start out talking about midlife, and wind their way to the power of telling the truth about your own life. In the middle, there’s grief: scary diagnoses, the deaths of friends, a near death experience, and some personal wake up calls to the meaning of life.

It’s Ok that You’re Not Ok in the mixed bag of midlife.

6 things you’ll learn in this episode:

• How “hospitality” manifests itself inside grief (and life)
• How suicide deaths in your friend group impact the rest of your life
• What it’s like facing a cancer recurrence *just* as you’re feeling yourself come back to life
• Why community is crucial to our survival
• Coming out as a gay man in the 1980’s, and what coming out to yourself might mean now
• Why you want multigenerational relationships, no matter how old you are now

Content note: this episode contains mention of suicide, along with brief mention of the method.

Related episodes:

Baratunde Thurston on the power of community

Notable quotes:

“One of the challenges with grief is the feeling like it will never end. If you can actually understand what it means to be in that messy middle, you can actually move through the grief more in a more natural, humane, and accelerated fashion.” - Chip Conley

“It is not required that you change the world because of what you've experienced in your life.” - Megan Devine

About our guest:

Chip Conley is a strategic advisor for hospitality and leadership at Airbnb, founder of the Modern Elder Academy, which helps people in their ‘third age’ find a new path forward, and author of Wisdom @ Work: The Making of a Modern Elder. He was a founder board member for Burning Man. Find him on social @ChipConley

About Megan:

Psychotherapist and bestselling author Megan Devine is recognized as one of today’s most insightful and original voices on grief, from life-altering losses to the everyday grief that we don’t call grief. She helms a consulting practice in Los Angeles and serves as an organizational consultant for the healthcare and human resources industries.

The best-selling book on grief in over a decade, Megan’s It’s Ok that You’re Not OK, is a global phenomenon that has been translated into more than 25 languages. Her celebrated animations and explainers have garnered over 75 million views and are used in training programs around the world.

Additional resources:

Want to talk with Megan directly? Join our patreon community for live monthly Q&A sessions: your questions, answered.

Chip’s book - Wisdom @ Work: The Making of a Modern Elder

Modern Elder Academy

Man’s Search for Meaning by Victor Frankl

The Rumi Collection: An Anthology of Translations of Mevlana Jalaluddin Rumi

Check out Megan’s best-selling books - It’s OK That You're Not OK and How to Carry What Can’t Be Fixed

Books and resources may contain affiliate links.

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