370. How to Fail Like a Pro

Episode Summary

Executive Summary: This episode argues that failure is not an exception to creativity but a core mechanism of it. Through stories from physics, writing, comedy, engineering, education, film, and visual art, it shows how creators iterate through setbacks, use failure as data, and often need to redefine success to keep making work.

Main Topics: Failure as an inevitable part of creative success: The episode opens with Saul Perlmutter’s supernova research to illustrate that major breakthroughs require prolonged periods of uncertainty, error, and repeated attempts before success emerges. Creative work as iterative experimentation: James Dyson and Mitch Resnick frame creativity as building, testing, failing, and refining—treating mistakes as information and experimentation as the path to better outcomes. Self-criticism, fear, and the inner critic: Writers, composers, and performers like Jennifer Egan, Nico Muhly, and John Hodgman describe the psychological burden of being both creator and critic, and how fear can block starting or finishing work. Success can itself create failure pressure: Jennifer Egan and Don Hahn explain that after major success, expectations can become paralyzing, leading to doubt, avoidance, and the fear of not matching earlier achievements. Reframing failure as productive information: Experts like Teresa Amabile and creators like Perlmutter and Vogt argue that setbacks provide useful feedback, help narrow what doesn’t work, and can even be desirable when they clarify the purpose of the work. Collaboration, imbalance, and creative partnerships: Mark Duplass reflects on how collaboration can both amplify and strain creativity, especially when partners have different rhythms, and how a separation can be healthy and creatively clarifying. Knowing when a form or format no longer fits: Conan O'Brien discusses reformatting his show to match audience behavior and the modern media environment, showing that failing to adapt can itself be a kind of creative failure.

Key Arguments: Major creative breakthroughs usually require many failures; they are not signs of weakness but evidence of active exploration. A tough problem is worth sustained effort because the process of trying teaches you what does not work and moves you closer to what does. Creative people often function as both boss and employee, which makes self-doubt, harsh self-talk, and paralysis common. Success can be destabilizing because it raises the stakes and makes later work feel like a test of identity rather than a normal project. A growth mindset reduces the emotional cost of failure by treating ability as improvable through practice and experimentation. In engineering and technology, failure is especially central because prototypes must be tested repeatedly before a design works. Creative education should encourage tinkering and safe risk-taking so children learn to recover from mistakes and iterate. Sometimes the right response to repeated failure is to change the medium, format, or collaboration structure rather than force the old model to continue. Failure can be redefined as success when the rejected outcome is more valuable to the creator than to the market, as in the case of Jorinde Voigt reclaiming her paintings. Partnerships can become creatively counterproductive if collaborators' rhythms clash; stepping back can preserve both the relationship and future creative output.

Data Points: Supernovae needed for measurement: 30 some odd - Perlmutter said they expected to need about thirty supernovae to measure the universe’s slowing expansion. Planned project duration: 3 years - The team originally proposed that finding enough supernovae would take at least three years. Telescope access obtained: 12 and a half nights - Perlmutter’s team traded a camera for limited telescope time at an Australian observatory. Useful telescope time actually received: 2 and a half nights - Bad weather reduced the usable observing time over three years. Failures before success in Dyson’s development process: 5,126 failures - James Dyson said he built 5,127 prototypes before arriving at the final vacuum design. Mozart success rate: 60 to 70% - Dean Simonton cited Mozart as an unusually successful hitmaker. Mozart implied failure rate: 30 to 40% - The episode translates Mozart’s hit rate into a failure rate to show even geniuses fail frequently. Duplass film budget that failed: $70,000 - Mark Duplass described an early feature film that cost about seventy thousand dollars and was never finished. Successful short film budget: $3 - The Duplass brothers made a later short film in their kitchen for only three dollars, which went to Sundance. Conan format change: 60 minutes to 30 minutes - Conan O'Brien reduced his late-night show runtime to better match the changing media landscape. Duplass HBO series seasons completed: 2 seasons - Togetherness ran for two seasons before cancellation. Pulitzer Prize: 1 - Jennifer Egan’s A Visit from the Goon Squad won a Pulitzer, which intensified pressure on her next book.

Pivotal Quotes: "failure is an inevitable component of success" — Stephen Dubner / episode framing: The episode’s central thesis, stated after Saul Perlmutter’s story. "It is the most rewarding thing that I can do, but it is a constant struggle" — John Hodgman: Hodgman describing the emotional tension of making creative work while fearing he has run out of ideas. "I had to build 5,127 prototypes. So there were 5,126 failures." — James Dyson: Dyson explaining how repeated prototyping and failure led to the final product.

Implications: For listeners and creative teams, the message is to normalize failure, use it as feedback, and keep iterating. The most durable careers come from resilience, adaptability, and choosing environments where risk is safe and useful.