Thiel described his years of competitive tracking — from middle school to high school to college to law school — all driven by the comfort of familiar tests and measurable success. He landed at a prestigious New York law firm that felt like Alcatraz: everyone outside wanted in, and everyone inside wanted out. When he lost a Supreme Court clerkship, he was devastated. But a decade later, a friend's first words to him were, 'Aren't you glad you didn't get that clerkship?' Because that loss was what finally broke him free from a track he'd been following since childhood without ever questioning where it led.