In this episode, I discuss How Will You Measure Your Life? by Clayton Christensen, James Allworth, and Karen Dillon—a book that takes the management theories Christensen taught at Harvard Business School and applies them to one of the most important questions we can ask ourselves: What makes for a fulfilling life?

Rather than relying on inspirational advice, Christensen argues that the same principles that help companies succeed can also help us make better decisions about our careers, relationships, and personal lives.

I spend most of the episode focusing on three ideas that stood out to me.

First is the concept of deliberate strategy vs. emergent strategy. We often believe we need to map out every step of our future, but Christensen shows that many of the most successful companies—and people—arrive somewhere they never originally planned. The key isn't predicting the future; it's having clear values while remaining flexible enough to recognize and pursue unexpected opportunities.

Next, I dive into motivation theory, exploring why money and external rewards only go so far. Christensen draws on research showing that while fair compensation matters, long-term fulfillment comes from meaningful work, opportunities to grow, responsibility, and making a genuine contribution. It's a useful framework for thinking about both our own careers and how we lead teams.

Finally, we discuss outsourcing—not just as a business decision, but as a life decision. Which responsibilities should you keep because they create meaning or strengthen relationships, and which are better delegated so you can spend more time on what matters most? Viewing your personal life through the same lens as resource allocation in business can lead to surprisingly powerful insights.

Whether you're building a company, managing a career, or simply trying to live more intentionally, this book offers practical mental models for aligning your daily decisions with the life you ultimately want to build.

Books referenced (affiliate links):

How Will You Measure Your Life?: https://amzn.to/4faaYjs

Top Five Regrets of the Dying: https://amzn.to/3TnA060

Getting to Plan B: https://amzn.to/4wH3uu6

The Innovator's Dilemma: https://amzn.to/4wcAzhH

Rise and Fall of Strategic Planning: https://amzn.to/3T7apOK

Discovery-Driven Growth: https://amzn.to/4yt5K9S

The Origin and Evolution of New Businesses: https://amzn.to/3T3z9ra