It is one of our enduring enigmas: iconic endeavors—from Nobel Prize-winning discoveries to entrepreneurial inventions and works in the arts—are often not achievements, but conversions, corrections after failed attempts. This panel considers this riddle of human enterprise. Taking the arts-inspired book The Rise by Sarah Lewis as a departure, the talk explores the irreplaceable gifts that have come from failure in creative endeavors. It reveals the inestimable value of often ignored ideas for entrepreneurship: What do the arts teach us about the cultivating of grit, the hallmark trait required for achievement? What are the breakthroughs that have come from "deliberate amateurs"? Why do near wins often later yield unprecedented triumph on the road to mastery?