Life Isn't Fair - Focus On What's Next

The worst thing a leader can do is hesitate on decisions. When faced with two terrible options, the psychological muscle you must build is the ability to look into the abyss and choose the slightly better path. This is especially difficult because the only value you add as a leader is when you make decisions most people don't like—if everyone agrees, they would have made that decision without you.

Ben Horowitz believes that leadership isn't about avoiding pain but running toward it. The most destructive leadership mistake is hesitation, which happens when both available choices seem horrible. For example, when Loudcloud went public with only $2 million in trailing revenue at 18 months old, it seemed insane—the Wall Street Journal wrote about how stupid it was, and Business Week called it "the IPO from Hell." But the alternative was bankruptcy, which would have been worse.

This courage to make difficult decisions comes from confidence, which founders often lose after making expensive mistakes. When a leader loses confidence, they hesitate, and senior team members jump into the void to make decisions themselves, creating a political, dysfunctional organization. Much of what a16z does is help founders maintain confidence through these inevitable struggles.

For CEOs specifically, Ben emphasizes that you can't develop people in areas where you lack expertise. While a VP of Engineering can develop engineers, a CEO can't realistically turn a mediocre CFO into a world-class one. Instead, CEOs need "managerial leverage"—finding people who bring ideas to you rather than you having to push them. As Ben puts it: "If I have the ideas about what your department should do next, that's no leverage. What's leverage is if you're telling me what you should do and how you can push the company forward."

The path to success isn't about avoiding failure but building resilience through it. Ben notes that "the median on the CEO test is like 18, not 90," meaning you have to be comfortable getting D-minuses because a D-minus is fine as long as you don't get an F. The psychological challenge is maintaining confidence while climbing the competency curve, which is why Ben believes C-minus students sometimes make better CEOs—they're used to failing.

This perspective explains why Ben wrote The Hard Thing About Hard Things—to normalize the struggle that every leader faces, contrary to the success narratives that make it seem like companies are built through genius ideas and smooth execution. Even the most successful founders like Mark Zuckerberg and Sam Altman go through the same struggles as everyone else.

The ultimate leadership lesson Ben shares is that how you feel about yourself will end up meaning as much as anything else. As one of his managers told him: "No credit will be given for predicting rain, only credit for building an ark." For leaders, it doesn't matter if you predict failure—you've still failed. What matters is figuring your way out of it.