You Weren’t Meant to Have a Boss

Paul Graham’s essay You Weren’t Meant to Have a Boss argues that humans are evolutionarily designed to work in small groups, and large organizations fundamentally conflict with our natural inclinations.

Natural Group Size

Humans thrive in groups of roughly 8 people, become difficult to manage around 20, and function poorly at 50+. Yet modern companies employ hundreds or thousands, necessitating hierarchical structures that constrain individual freedom.

The Tree Problem

Large organizations adopt tree structures with managers as connecting points. This creates a critical issue: as organizational size grows, individual freedom shrinks proportionally.

Each person’s autonomy decreases because “each group tries its best to work as if it were the small group” it was designed to be.

The Food Analogy

Corporate jobs resemble junk food—immediately appealing but ultimately damaging. They offer salary and prestige but extract a psychological cost through constrained autonomy and diminished mental engagement.

Impact on Programmers

Programmers suffer especially in large companies because programming requires constant innovation. Yet bureaucratic structures resist novelty. Even at Google, programmers can’t implement many desired ideas due to legacy code and organizational overhead.

My Takeaway

This essay recommends ambitious programmers pursue startups or small companies rather than large corporations. Working independently aligns with human nature in ways big organizations cannot.