No Stupid Questions
No Stupid Questions

43. What Do We Really Learn From Failure?

Also: what is teasing supposed to accomplish? This episode originally aired on March 14, 2021.

Featured Speakers

Stephen Dubner Guest

Topics Discussed

Episode Summary

Executive Summary: The episode first examines why Stephen Dubner ended the live game show Tell Me Something I Don't Know: it was fun and fruitful, but hard to make excellent both as a live event and as a polished podcast. The second half explores teasing as playful bonding that depends heavily on status, setting, and nonverbal cues—especially difficult in virtual communication.

Main Topics: Why Tell Me Something I Don't Know ended (Priority: 5/5): Dubner explains that the live show was enjoyable and valuable, but the team could not make it simultaneously great for the live audience and for later audio editing without sacrificing other work. Learning from failure and knowing when to stop (Priority: 5/5): The hosts frame the show’s end as a productive failure: it revealed what Dubner’s team does well, what core competence means, and why stopping can be the right strategic choice. Core competence and portfolio thinking (Priority: 4/5): Dubner argues that organizations and individuals should focus on what they are best at while treating experimental projects like a portfolio—keeping risky ideas alongside safer ones. The psychology of teasing (Priority: 5/5): The second segment asks what teasing accomplishes, concluding that it often serves affiliation, bonding, and oblique communication rather than literal insult. Status, power, and context in teasing (Priority: 5/5): The hosts emphasize that teasing usually flows downward in status hierarchies and can become threatening or awkward when power differences are ignored, especially at work or online. Nonverbal cues and the limits of virtual communication (Priority: 4/5): They note that teasing relies on tone, timing, and facial expression—signals that are weakened or lost in video calls, texts, and other mediated settings. Roasts, joking, and public discomfort (Priority: 3/5): The conversation ends by distinguishing playful roasting from cruelty, with both hosts acknowledging discomfort around public humiliation humor even while recognizing its social role.

Key Arguments: A project can be worthwhile even if it eventually ends, as long as it generates learning, relationships, and transferable skills. Tell Me Something I Don't Know could not meet two incompatible goals at once: being excellent live and excellent as an edited podcast. Dubner sees failure as useful when it clarifies process flaws, task difficulty, and complexity rather than personal incompetence. Organizations should encourage experimentation, but risky bets are easier for people with control over their own schedules and careers than for most employees. Teasing is usually meant to bond, provoke indirectly, or broach delicate topics, not merely to insult. Status matters: teasing from higher to lower status is safer than the reverse, and teasing up the hierarchy can be risky. Video calls and text strip away the cues that tell listeners not to take teasing literally, making misunderstanding more likely. Roasts can expose social truths, but they also make some listeners cringe because they border on humiliation.

Data Points: California live shows: 2 - Dubner says Tell Me Something I Don't Know had one show in San Francisco and one in Los Angeles. Taping length: 3.5 hours - At one point, the team recorded a three-and-a-half-hour taping to produce a 45-minute podcast. Podcast length target: 45 minutes - The edited audio they hoped to extract from the long live taping. Estimated audience size: 1,000 to 2,000 - Dubner contrasts the small live audience with the much larger later podcast audience. Potential podcast audience: 1 million to 2 million - Dubner describes the later listening audience he prioritized when judging the project. Success rate estimate: 95% - Dubner says roughly 95% of people involved or attending had a great time. Tenure clock: zero or one - Duckworth describes the all-or-nothing pressure of tenure early in her career. White House Correspondents dinner attendance since: 1983 - The fact check notes the featured comedian tradition began in 1983. Presidents attended the White House Correspondents dinner: 15 - The fact check states 15 presidents have attended since the event began. Reagan absence year: 1981 - Reagan did not attend because he was recovering from an assassination attempt.

Pivotal Quotes: "It was mostly fun, but it wasn't as good ever as I wanted it to be, and therefore it became a lot less fun." — Stephen Dubner: Dubner explains why he decided to end Tell Me Something I Don't Know. "I think teasing is like gravity. It usually flows downward." — Angela Duckworth: Duckworth summarizes her view that status strongly shapes who teases whom. "Might not work, might not be fun, might lose a ton of money, but let's try it and see how well we can do." — Stephen Dubner: Dubner describes the spirit of experimental work, while noting that most people cannot take such risks easily.

Implications: Try experiments, but know when a project’s structure makes excellence unlikely. Teasing can strengthen relationships, but only when status, mood, and medium make it safe and clearly playful.

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