How Will You Measure Your Life? (Most of Us Get It Wrong) with Karen Dillon & Charles Good | TGLP #282
Mon Feb 02 2026
In this episode of the Good Leadership Podcast, host Charles Good speaks with Karen Dillon, former editor of Harvard Business Review and co-author of 'How Will You Measure Your Life?'
They explore the intersection of business theory and personal fulfillment, discussing how rigorous decision-making and understanding intrinsic motivation can lead to a more satisfying life. Dillon shares insights from her collaboration with Clayton Christensen, emphasizing the importance of applying business theories to personal decisions, the high achiever paradox, and the significance of relationships in achieving long-term happiness.
Chapters
00:00 Introduction to Karen Dillon's Journey
02:19 The Impact of Clay Christensen's Teachings
04:47 Understanding Business Theory and Life Decisions
07:17 Herzberg's Two Factor Theory Explained
09:29 The Importance of Intrinsic Motivators
11:11 Self-Check for Long-Term Fulfillment
12:04 Deliberate vs. Emergent Strategy in Business
14:30 Testing Assumptions in Decision Making
16:33 Financial Constraints Leading to Innovation
18:53 The High Achiever Paradox
22:22 Jobs to Be Done Theory in Relationships
27:25 Understanding Emotional Needs in Relationships
29:09 Outsourcing Responsibilities: Lessons from Dell
32:06 Key Insights and Takeaways
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In this episode of the Good Leadership Podcast, host Charles Good speaks with Karen Dillon, former editor of Harvard Business Review and co-author of 'How Will You Measure Your Life?' They explore the intersection of business theory and personal fulfillment, discussing how rigorous decision-making and understanding intrinsic motivation can lead to a more satisfying life. Dillon shares insights from her collaboration with Clayton Christensen, emphasizing the importance of applying business theories to personal decisions, the high achiever paradox, and the significance of relationships in achieving long-term happiness. Chapters 00:00 Introduction to Karen Dillon's Journey 02:19 The Impact of Clay Christensen's Teachings 04:47 Understanding Business Theory and Life Decisions 07:17 Herzberg's Two Factor Theory Explained 09:29 The Importance of Intrinsic Motivators 11:11 Self-Check for Long-Term Fulfillment 12:04 Deliberate vs. Emergent Strategy in Business 14:30 Testing Assumptions in Decision Making 16:33 Financial Constraints Leading to Innovation 18:53 The High Achiever Paradox 22:22 Jobs to Be Done Theory in Relationships 27:25 Understanding Emotional Needs in Relationships 29:09 Outsourcing Responsibilities: Lessons from Dell 32:06 Key Insights and Takeaways