561. How to Succeed at Failing, Part 1: The Chain of Events

The devastating Lahaina wildfire wasn’t just a tragedy; it was a predictable and preventable chain of failures, from untrimmed dry grass to a shattered emergency alert system. This concept—that failure is rarely a single event but a sequence of missed opportunities and small errors—frames a deep exploration into why we fail to learn from failure. Through conversations with experts ranging from an astrophysicist-turned-fire-safety engineer to organizational psychologists and a school shooting data researcher, the discussion dismantles the simplistic Silicon Valley mantra to “fail fast,” arguing instead for a more nuanced understanding.

The podcast distinguishes between different types of failure, from the preventable “bad” failures in systems like healthcare or aviation to the inevitable “intelligent” failures that accompany ambitious innovation. A key tension emerges between the emotional need to feel the sting of failure to drive learning and the social fear of shame that causes us to hide our mistakes. This fear is examined through a gendered lens, with evidence suggesting women often feel a lower “license to fail” in professional settings, making them more risk-averse in classrooms and boardrooms.

This framework is then powerfully applied to one of the most urgent and heartbreaking failures: school shootings. The analysis reveals that each shooting represents the catastrophic end point of a long chain where every single preventative intervention—from a parent checking a safe to a counselor interpreting a warning sign—failed. Conversely, the research shows that breaking just one link in that chain, often through simple human connection and a systematic response to red flags, can avert tragedy. The episode concludes by reframing failure not as an inevitable doom but as a series of points where human choice and improved systems can create a virtuous, rather than vicious, circle.

Surprising Insights

• Failure is a chain, not a moment. Catastrophes like the Lahaina fire or a school shooting are the final result of numerous sequential failures where intervention at any point could have changed the outcome.
• A “failure-free life is not a possibility.” Experts argue that falling short is an inherent part of the human condition and of progress, making our goal not to eliminate failure but to fail more wisely.
• The U.S. may lead the world in failure—and that’s a key to its success. An economist argues that America’s greater cultural and legal tolerance for failure (e.g., more forgiving bankruptcy laws) fuels higher rates of entrepreneurship and innovation compared to many European nations.
• School safety cannot be a “learning culture.” Unlike sectors like tech, where experimentation is valued, the consequences in school safety are so dire that the focus must be on preventing the first failure through proven systems, not learning from repeated tragedies.
• The most effective tool to prevent a school shooting might be simple human compassion. Interviews with averted shooters reveal that a single act of kindness, making a troubled person feel seen and valued, can break the chain of events leading to violence.

Practical Takeaways

• Reframe failure as a diagnostic tool. Instead of asking “Who’s to blame?” ask “What are the multiple causes in the chain of events?” Look beyond the immediate, “sharp-end” mistake to systemic contributors.
• Share failures to accelerate collective learning. Actively discussing what went wrong, especially in organizations, prevents others from wasting time repeating the same mistakes and builds psychological safety for smarter risk-taking.
• Distinguish between types of failure. Not all failures are equal. Learn to identify preventable failures (which require better processes) from unavoidable complexities or intelligent failures from worthwhile experiments (which should be analyzed for insight).
• For systemic threats, prioritize prevention over reaction. As with the proposed National Crisis Center model, invest in upstream systems—like universal threat assessment protocols and community crisis resources—that can break chains of failure before they reach a point of no return.
• Practice intentional kindness as a risk-mitigation strategy. On a human level, proactively reaching out to isolated or struggling individuals can address the root of many potential crises, from personal breakdowns to community violence.