When To Do What You Love

Paul Graham’s essay When To Do What You Love reframes the “follow your passion” debate as fundamentally complex.

The Core Tension

“All other things being equal, why wouldn’t you work on what interests you the most?” But circumstances rarely allow this luxury.

The Money-Interest Trade-off

When earning is the primary goal, pursuing passionate interests typically conflicts with income. However, exceptions exist—particularly when someone possesses rare talent combined with genuine interest.

The Wealth Paradox

Moderate wealth-seeking often requires abandoning passionate work. But aspiring to “hundreds of millions or billions of dollars” actually benefits from pursuing genuine interests.

Startup founders frequently succeed because their passionate projects align with market needs that others overlook.

Addressing Uncertainty

For those genuinely undecided, Graham recommends experimentation rather than analysis. Start early to explore different fields—”figuring out what to work on is a problem that could take years to solve.”

Strategic Considerations

• Choose colleagues carefully since “you’ll become like whoever you work with”
• Stay “upwind”—select paths offering maximum future flexibility

The Great Work Requirement

Pursuing passionate work becomes essential only for those seeking great achievements. It’s a necessary but insufficient condition for excellence.

How do you balance passion and practicality? I’d love to hear at persdre@gmail.com.