Book Review: How Will You Measure Your Life? by Clayton Christensen

A few weeks ago, I picked up How Will You Measure Your Life? by Clayton Christensen, and wow—this book hit me harder than I expected. It’s one of those rare reads that quietly reshapes how you think about work, relationships, and what it actually means to live a good life.

So in classic fashion, I wanted to share some of my key takeaways, why this book matters, and whether it’s worth your time.

Actually, Christensen—famous for coining "disruptive innovation"—takes the tools we usually apply to building businesses and flips them to help us design our lives. Think of it like this: what if you treated your career, your relationships, and your personal values like a startup? Would they be thriving—or quietly running on autopilot?

The book is structured around three questions:

1. How can I be sure that I’ll be happy in my career?

2. How can I be sure that my relationships will be a source of joy?

3. How can I be sure I won’t lose my integrity and end up like Enron executives or in jail? (Yes, it gets real.)

Here’s my favorite highlights as I went through the book: 

1. Don’t outsource your happiness

Christensen argues that chasing prestige, money, or other people’s definitions of success often leads to unfulfilling careers. Instead, focus on what motivates you intrinsically—what he calls the “job to be done” in your life.

It reminded me of the Ikigai framework: doing work that you love, that you’re good at, that the world needs, and that pays enough to sustain your lifestyle.

2. How you spend your time = your actual priorities

You can say you care about your family, but if you’re spending 80% of your week at work and the rest scrolling LinkedIn and trying to "optimize" your life, then your actions don’t match your values.

That hit me. I’ve been guilty of chasing productivity for its own sake. This was a reminder to allocate time intentionally, not just efficiently.

3. Success doesn't always look like success

Some of Christensen’s classmates from Harvard went on to incredible careers—but personal disasters. Divorces, estranged children, even prison. The point? Long-term fulfillment isn't about being the best on paper—it’s about living in alignment with your principles.

So, who Should Read It?

• If you're early in your career and feeling the tension between ambition and authenticity.

• If you're in a “successful” job but wondering if this is all there is.

• If you love frameworks and want to apply them beyond startups and strategy decks.

How Will You Measure Your Life? isn’t a typical self-help book. It’s not prescriptive or cheesy. It’s thoughtful, grounded, and full of gentle prompts that nudge you toward better questions. It’s especially great if you’re into books like The Pathless Path by Paul Millerd. Highly recommend reading this one slowly, maybe even journaling your answers as you go. This book isn’t about fixing your life—it’s about understanding what you want your life to be in the first place.