I Quit Being a Tech CEO at 40: The "Obituary Moment" - Ken Davenport

What do you do when you are a successful Tech CEO in your 40s, checking every box of societal success, but you realize the story you are writing with your life isn't worth reading?Ken Davenport, author of *The Virtue Ethos* and co-founder of Mission Edge, calls this his "Obituary Moment." In this episode, he shares the courageous story of quitting his company to find a life of actual meaning through Stoic philosophy. He opens up about the ego death of leaving the C-suite and why his friends thought he needed a psychologist when he walked away from the money.This episode dives into the FailCraft theme of rewriting your story before it’s too late. Ken explains how he used the ancient wisdom of Stoicism—specifically the "Dichotomy of Control"—to navigate the chaos of modern life.Discover why "we suffer more in imagination than in reality", how to shift from a for-profit mindset to a mission-driven life, and why true success has nothing to do with your bank account.In this episode of FailCraft, you’ll discover:* The "Obituary Moment": Realizing your current life story isn't worth reading.* Ego vs. Purpose: Why financial success is often a hollow victory.* The Stoic Framework: Using the "Dichotomy of Control" to stop anxiety.* Why friends thought Ken was "crazy" for quitting his CEO role.* Seneca's Wisdom: Why we suffer more in our heads than in real life.* The transition from For-Profit CEO to Non-Profit Founder (Mission Edge).* The 4 Virtues: Wisdom, Courage, Discipline, Justice (and why Wisdom is the hardest).* Ken's definition of true success: Impact over Income.This episode is for anyone feeling stuck in a "successful" but unhappy life, entrepreneurs looking for a deeper purpose, or anyone interested in applying Stoic philosophy to the real world.Connect With Ken Davenport:* Website & Books:https://www.kendavenport.net/* Nonprofit: https://missionedge.org/* LinkedIn: https://www.linkedin.com/in/kgdavenport/Support the Show: * Fuel the FailCraft Mission: https://iferia.nestuge.com/supportme * Subscribe and leave a review! * Share this episode if it resonated!Want to Be a Guest on FailCraft? * Reach out to Ezekiel on PodMatch * PodMatch Host Profile: https://podmatch.com/hostdetailpreview/failcraftChapters:00:00 Hook: The Nagging Feeling of an Empty Life01:18 Introduction: Ken Davenport's Pivot01:51 The "Obituary Moment": Facing an Existential Crisis03:53 Letting Go of the CEO Ego & Identity06:03 Stoicism 101: The Dichotomy of Control08:52 Seneca's Rule: Surviving Your Own Imagination10:50 Building Mission Edge: Purpose Over Profit13:04 The 4 Virtues: Why Wisdom is the Hardest16:54 Ken's Definition of True Success18:27 How to Connect & Learn Stoicism