Midlife Transitions: How to Lean in Rather than Resist the ‘Messy Middle’ with Chip Conley

Reimagining Love

When it comes to life stages, “midlife” often gets the short end of the stick. We speak about adolescence and retirement as vistas rich with opportunity and possibility while we joke about midlife and its related crises. However, when we adopt an affectionate perspective, opportunity and joy prove to be just as possible in this “messy middle” stage.

Many transitions take place over the decades following age 50. These milestones are no less impactful than those we celebrate, such as graduation and marriage, and yet most of us lack rituals to mark these evolutions and help us build communities of support in this time of great potential.

Chip Conley was a disruptive force in the hospitality industry for decades. In 2018, he combined his experiences mentoring at Airbnb with his own midlife transition to launch the Modern Elder Academy (MEA). Today, the world's first “midlife wisdom school” offers luxurious, personal growth retreats in Baja California and New Mexico. Chip is also the author of seven books, including his most recent, Learning to Love Midlife.

In December 2024, Dr. Alexandra will be at the Santa Fe ranch location of MEA leading a 5-day retreat for couples centered on healing the past, deepening connection, and creating a relational vision for the future. You can attend with your partner or on your own. To learn more about the retreat, Loving You Without Losing Me: A Retreat for Couples, visit the website and schedule a free consultation call with the MEA admissions team.

Whether you are approaching midlife, are in the midst of it, or if midlife is in your rearview mirror, Chip’s affectionate and curious approach to this often overlooked and undervalued stage will illuminate new outlooks and possibilities for how we lean into life’s transitions.

Relevant Links:

• Read Chip’s latest book Learning to Love Midlife
• Learn more about Chip and get his free Anatomy of a Transition resource on his website
• Learn more about Dr. Alexandra’s December 2024 retreat at MEA
• Order Dr. Alexandra's new book, Love Every Day
• Subscribe to Dr. Alexandra’s Newsletter
• Submit a Listener Question

Join Dr. Alexandra's five-day retreat with the Modern Elder Academy — Get 10% off with code 'GF10'

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Hey Reimagining Love Listeners! Quick note here that we’re going to be on a very short two week break starting Sept 17th. When we return on October 1st, we’re going to start publishing new episodes on an every other week schedule with occasional bonus episodes sprinkled throughout. If you're craving more content in the meantime, you can always search the back catalog and/or find juicy blog posts and other resources at dralexandrasolomon.com.