The Questions That Defines Your Legacy with Karen Dillon and Charles Good | TGLP $288

In this episode of The Good Leadership Podcast, Charles Good sits down with Karen Dillon, co-author of the New York Times bestselling book How Will You Measure Your Life?, to explore one of the most important questions any of us can ask. Most people measure their lives using the wrong metrics—titles, achievements, money, or recognition. But those measures rarely capture what truly matters. Drawing on the work of the late Clayton Christensen, Karen explains how our daily decisions about where we invest our time, energy, and attention quietly shape the kind of life we end up living. This episode challenges listeners to rethink how they define success and to start aligning their daily choices with the person they ultimately want to become. If you’ve ever wondered whether you’re investing your time and energy in the right things, this conversation will give you a powerful framework for thinking about your career, relationships, integrity, and legacy. CHAPTERS 00:00 The Importance of Allowing Children to Face Challenges 01:50 Rethinking Leadership Development: McCall's Theory 04:47 Creating Valuable Experiences for Growth 07:16 Deliberate Family Culture: Building Values Together 11:07 Reinforcing Values in Organizations and Families 14:40 The Trap of Marginal Thinking 21:29 Measuring a Meaningful Life 24:10 Balancing Life's Investments 24:50 Practical Actions for a Fulfilling Life 27:23 Key Insights and Takeaways #HowWillYouMeasureYourLife #IMS #ClaytonChristensen #LifePurpose #MeaningfulLife #outlearn #outlearntooutperform