In How Will You Measure Your Life, renowned HBS professor Clayton Christensen (of Innovator’s Dilemma fame) explores happiness and fulfilment. The core thesis is that most people, even the most intelligent and ambitious people in the world (or perhaps them especially), don’t adequately strategise about their long-term happiness, leading to lives that may be full of successes on paper but underneath are swimming in regret.

Each chapter outlines a particular area of life that Christensen feels is important (e.g, career choice, parenting, integrity), and provides a relevant management theory, along with a business case to illustrate its use, and many personal anecdotes to support the application of the theory to personal lives.

I was worried that the book would be a variety of cringeworthy applications of management theories to personal life – loose analogies rather than applicable mental models. This is somewhat true in the second half of the book as Christensen explores marriage and parenting, but generally, the theories seem useful and well-chosen, especially in the context of job satisfaction.

Christensen’s book is an important read for young ambitious people because it highlights an unpleasant possible future world: one in which you achieve the things that you currently want, but end up deeply unhappy because you’ve been optimising under a misspecified utility function.

Key ideas

• Core thesis: people don’t strategise about what will make them happy
  • instead, they focus on near-term heuristics like money and career success without considering what will create long-term meaning
  • career is certainly part of that, but people often optimise for this at the expense of “investing” in relationships and family, which for most people end up being the dominant contributor to happiness and fulfilment.
• Job satisfaction: Herzberg’s Two-Factor Theory of Motivation:
  • job satisfaction and dissatisfaction are two orthogonal axes
  • hygiene factors determine dissatisfaction: comp (!), job security, work conditions, bureaucracy.
  • motivators create satisfaction: intrinsic growth, mastery/achievement
  • in jobs like trading, money is a motivator because it is so correlated with growth/mastery/performance.
• Serendipity vs planning:
  • Honda case study: dirt bike was a serendipitous offshoot of struggles to launch a motorbike in the US in the 60s.
  • Deliberate vs emergent strategy:
    • deliberate makes sense if you are confident you have found a fulfilling path
    • Discovery-driven planning is a technique to balance deliberate and emergent strategies
• Capabilities theory:
  • companies should look at capabilities to understand what should be done in-house vs outsourcing
  • capabilities are either: resources, processes, priorities
  • likewise, when raising children, some things need to be done in-house
• Marginal thinking:
  • an overall strategy is the sum of tactics. “one-off” misaligned tactics done repeatedly lead to a bad strategy.
  • The marginal cost of doing something “just this once” always seems to be negligible, but the full cost will typically be much higher.

Highlights

• Thesis
• Theories and mental models
• Career satisfaction
• Balancing planning with serendipity
• Underinvestment in personal life
• Marriage
• Parenting
• Developing experiences