From CEO to Soup Kitchen | How Stephen Keys Achieved His Midlife Reinvention. episode artwork

EPISODE · Mar 23, 2026 · 1H 6M

From CEO to Soup Kitchen | How Stephen Keys Achieved His Midlife Reinvention.

from Don't Let The Old Man In

In this week's episode of Don't Let the Old Man In, we sit down with Stephen Keyes, a former CEO, to discuss the critical importance of owning one's mistakes and confronting life's challenges, especially when pursuing a reinvention. Stephen shares his personal reinvention journey, including the profound impact of his divorce, offering valuable life advice on how to overcome challenges in life. This episode is a must-listen for anyone navigating personal development and seeking personal growth through difficult times.In this episode we cover:Owning Your Mess: A Journey of Self-DiscoveryThe Pain of Divorce: A Personal PerspectiveNavigating Loneliness and Rebuilding RelationshipsVolunteering: Finding Purpose in ServiceCreating New Connections with ChildrenThe Importance of Community in MidlifeTransitioning from Success to Significance 20:14The Power of Collective ActionLessons from Volunteering: Giving BackRedefining Identity Through Community EngagementThe Power of Dignity in GivingRunning for a Cause: The Journey of an Ultra MarathonerThe Writer's Journey: Finding Voice and PurposeCareer Transitions: From CEO to CSR AdvocateBuilding the IFS Foundation: Community Impact and EducationThe Greatest Gift: Finding Meaning Beyond Career SuccessCreating Community: The Wisdom Vault and Midlife ConversationsIntegrating Life's Parts: A Journey of Self-DiscoveryFacing Complexity: The Hero's Journey in MidlifePod O'Sullivan brings you the weekly midlife learning podcast: from taking charge of your health, to strengthening your relationships, and finding ways to reconnect with what lifts your spirit – Don’t Let the Old Man In is designed to make sure your second act is even better than the first. Where career pivots, relationship evolutions, and personal reinventions meet practical wisdom, genuine brotherhood, and a healthy dose of humor. Hosted on Acast. See acast.com/privacy for more information.

In this week's episode of Don't Let the Old Man In, we sit down with Stephen Keyes, a former CEO, to discuss the critical importance of owning one's mistakes and confronting life's challenges, especially when pursuing a reinvention. Stephen shares his personal reinvention journey, including the profound impact of his divorce, offering valuable life advice on how to overcome challenges in life. This episode is a must-listen for anyone navigating personal development and seeking personal growth through difficult times.In this episode we cover:Owning Your Mess: A Journey of Self-DiscoveryThe Pain of Divorce: A Personal PerspectiveNavigating Loneliness and Rebuilding RelationshipsVolunteering: Finding Purpose in ServiceCreating New Connections with ChildrenThe Importance of Community in MidlifeTransitioning from Success to Significance 20:14The Power of Collective ActionLessons from Volunteering: Giving BackRedefining Identity Through Community EngagementThe Power of Dignity in GivingRunning for a Cause: The Journey of an Ultra MarathonerThe Writer's Journey: Finding Voice and PurposeCareer Transitions: From CEO to CSR AdvocateBuilding the IFS Foundation: Community Impact and EducationThe Greatest Gift: Finding Meaning Beyond Career SuccessCreating Community: The Wisdom Vault and Midlife ConversationsIntegrating Life's Parts: A Journey of Self-DiscoveryFacing Complexity: The Hero's Journey in MidlifePod O'Sullivan brings you the weekly midlife learning podcast: from taking charge of your health, to strengthening your relationships, and finding ways to reconnect with what lifts your spirit – Don’t Let the Old Man In is designed to make sure your second act is even better than the first. Where career pivots, relationship evolutions, and personal reinventions meet practical wisdom, genuine brotherhood, and a healthy dose of humor. Hosted on Acast. See acast.com/privacy for more information.

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From CEO to Soup Kitchen | How Stephen Keys Achieved His Midlife Reinvention.

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This episode was published on March 23, 2026.

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In this week's episode of Don't Let the Old Man In, we sit down with Stephen Keyes, a former CEO, to discuss the critical importance of owning one's mistakes and confronting life's challenges, especially when pursuing a reinvention. Stephen shares...

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