Episode 15: Dr. James Hollis Joins Man in the Middle (Our Exclusive Interview)

“Dr. James Hollis Joins Man in the Middle (Our Exclusive Interview)”
Episode Overview

What happens when the life you worked so hard to build suddenly feels too small?

In this rare and deeply reflective conversation, Kevin and Joe sit down with Dr. James Hollis to explore the inner crisis many men face in midlife, when achievement no longer satisfies, certainty dissolves, and the soul begins asking different question

Why listen

Dr. James Hollis is a renowned Jungian analyst and the author of more than 19 books, including The Middle Passage, a foundational work that has given language to the psychological and spiritual transition of midlife. His writing has guided generations of men through the often unspoken inner reckoning of the second half of life

Key Quotes

“The ego never knows enough to know enough.”

“The question of the second half of life is not what the world wants from me—but what the soul wants of me.”

“You are not crazy. There is a purpose to what is breaking down.”

“The smallest thing with meaning is greater than the largest thing without it.”

Main Topics Covered

1. The psychology of midlife transition
2. First adulthood vs. second adulthood
3. Why achievement can become a prison
4. Depression as a summons, not a disorder
5. Energy, meaning, and inner authority
6. Shadow work and the unlived life
7. Dreams as guidance systems
8. Patience, endurance, and courage
9. Masculinity, isolation, and authenticity
10. Legacy beyond success

Key Takeaways

1. Midlife unrest is not failure, it is initiation.
2. Letting go of old identities is necessary before new meaning emerges.
3. Feelings, energy levels, and dreams are diagnostic tools, not inconveniences.
4. The second half of life asks for service, not status.
5. This journey cannot be rushed but it can be honored.

Recommended Resource

1. The Middle Passage by James Hollis (a foundational text for men in midlife)
2. Audiobook versions of Hollis’ work, read by the author
3. Prisms and other writings by James Hollis

Next Steps

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