The New Midlife Male: Welcome to the Most Passionate, Powerful, Productive, and Purposeful Time of Your Life 

 January 26, 2024

By  Jed Diamond

Part 2

            In Part 1, I introduced readers to an expanded understanding of midlife and the unique journey that men make as we embark on what for many is a true hero’s journey.  In his pathfinding new book, Learning to Love Midlife: 12 Reasons Why Life Gets Better With Age, Chip Conley offers a unique guide for every man (and woman) who is dealing with the confusing and challenging time known as “midlife.”

            Chip Conley is CEO of the Modern Elder Academy, the first midlife wisdom school, and a New York Times bestselling author. “What’s wrong with me?” Chip asked himself in the Introduction to Learning to Love Midlife.

“That was the question that haunted me in my mid-40s,” says Conley. “I hated my life, partly because every piece of it was falling apart. Yet I clung to those pieces as if they were a tattered life preserver.”

            I first med Chip Conley shortly after he opened the Phoenix Hotel in San Francisco in 1987. I was planning a men’s retreat and his quirky hotel seemed like the perfect place. He went on to create a string of boutique hotels, Joie de Vivre Hospitality, and became the second-largest operator of boutique hotels in the world. He later became a mentor to the young entrepreneurs who started Airbnb and was named the company’s Head of Global Hospitality and Strategy.

            I recently interviewed Chip for a podcast at MenAlive. You can see the full interview here. I asked him about his own challenges in midlife, how he came to write the book, and his belief that midlife extends from age 35 to 75.

            I’ve been writing about midlife since 1997 when my book, Male Menopause, was published and become an international bestseller translated into fourteen foreign languages. I said,

“Male menopause, also called Andropause or Manopause, begins with hormonal, physiological, and chemical changes that occur in men generally between the ages of forty and fifty-five. These changes affect all aspects of a man’s life. Male menopause is thus, a physical condition with psychological, interpersonal, social, and spiritual dimensions.”

            I went on to say,

“My first experience with this change of life occurred the day I was born on December 21, 1943. When my mother announced, “it’s a boy,” and lifted me up for my father to hold, he was thirty-seven years old and in the midst of a major life crisis. Over the next five years, he became increasingly depressed and withdrawn. He had what my mother called ‘a midlife nervous breakdown.’ Just before my sixth birthday, he took an overdose of sleeping pills. Though he didn’t die, our lives were never again the same.”

            He was committed to the state mental hospital in Camarillo, north of our home in Los Angeles. I wrote about his own journey of survival and redemption in my book, My Distant Dad: Healing the Family Father Wound. Too many men hit midlife with little understanding, preparation, or guidance. Chip Conley’s journey was not as rocky as my father’s, but he faced his own difficult challenges. “I felt completely alone,” says Chip of this period in his life, “an idiot without a village.”

            He goes on to say,

“Midlife is when we begin to worry that life isn’t turning out the way we expected. We may feel a sense of lost opportunity and frustrated longings. Or feel that we’ve sold out and are living someone else’s life. It’s when we can look in the mirror and see a stranger.”

Chip talks about The Midlife Unraveling.

“Midlife is the initiation into a time of massive transitions. A drizzle of disappointments. Parents passing away, kids leaving home, financial reckonings, changing jobs, changing spouses, hormonal wackiness, scary health diagnoses, addictive behaviors becoming unwieldly, and the stirrings of a growing curiosity about the meaning of life.” (What’s it all about Alfie?)

Chip offers a wonderful vision of a positive transformation in the midst of the unraveling.

“When a caterpillar is fully grown, it uses a button of silk to fasten its body to a twig and then forms a chrysalis. Within this protective chrysalis, the transformational magic of metamorphosis occurs. While it’s a bit dark, gooey, and solitary, it’s a transition, not a crisis. And of course, on the other side is a beautiful butterfly.”

The 12 Reasons Why Life Gets Better With Age

            Chip details five important areas of our lives and within each one he offers a number of positive and transformative things we can address:

The Physical Life

  1. “I Have More Life Left Than I Thought.”
  2. “I’m Relieved My Body No Longer Defines Me.”

The Emotional Life

  • “I’m Making Friends With My Emotions”
  • “I Invest in My Social Wellness.”
  • “I Have No More ‘Fucks’ Left to Give.”

The Mental Life

  • “I’m Mastering My Wisdom.”
  • “I Understand How My Story Serves Me.”
  • “I’ve Learned How to Edit My Life.”

The Vocational Life

  • “I’m Joyfully Stepping Off the Treadmill.”
  • “I’m Starting to Experience Time Affluence.”

The Spiritual Life

  1. “I’ve Discovered My Soul.”
  2. I Feel As If I’m Growing Whole.”

You can learn more about Chip and his work and order his book by visiting him here. You will learn more about his new book, Learning to Love Midlife: 12 Reasons Why Life Gets Better With Age, his six other books, courses, and classes.

If you’d like to read more articles by me, you can sign up for my free newsletter here.

Best Wishes,

Jed Diamond


Founder and VHS (Visionary Healer Scholar) of MenAlive

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